Subscribe to RSS
DOI: 10.1055/s-0030-1260966
Odorless Eco-Friendly Synthesis of Thio- and Selenoglycosides in Ionic Liquid
Publication History
Publication Date:
25 July 2011 (online)
Abstract
An environmentally benign odorless methodology for the preparation of 1,2-trans-thio- and selenoglycosides is reported. In a one-pot condition, the reductive cleavage of disulfides and diselenides using triethylsilane and borontrifluoride diethyletherate combination followed by the reaction of the in situ generated thiolate and selenoetes with glycosyl acetate derivatives in recyclable room-temperature ionic liquid, [BMIM]˙BF4 resulted in excellent yields of thio- and selenoglycosides avoiding the use of obnoxious thiols/selenols and metallic catalysts.
Key words
thioglycoside - selenoglycoside - disulfide - diselenide - triethylsilane - ionic liquid
- Supporting Information for this article is available online:
- Supporting Information
-
1a
Oscarson S. In Carbohydrates in Chemistry and Biology Vol. 1:Ernst B.Hart GW.Sinay P. Wiley-VCH; Weinheim: 2000. p.93-116 -
1b
Nicolaou KC.Ueno H. In Preparative Carbohydrate ChemistryHanessian S. Marcel Dekker; New York: 1997. p.313-338 -
2a
Tsai TYR.Jin H.Wiesner K. Can. J. Chem. 1984, 62: 1403 -
2b
Wuts PGM.Bigelow SS. J. Org. Chem. 1983, 48: 3489 -
2c
Lear MJ.Yoshimura F.Hirama M. Angew. Chem. Int. Ed. 2001, 40: 946 -
2d
Nicolaou KC.Dolle RE.Papahatjis DP.Randall JL. J. Am. Chem. Soc. 1984, 106: 4189 -
2e
Dolle RE.Nicolaou KC.
J. Am. Chem. Soc. 1985, 107: 1691 -
2f
Nicolaou KC.Bockovich NJ.Carcanague DR.Hummel CW.Even LF. J. Am. Chem. Soc. 1992, 114: 8701 -
3a
Codee JDC.Litjens REJN.van den Bos LJ.Overkleeft HS.van der Marel GA. Chem. Soc. Rev. 2005, 34: 769 -
3b
Garegg PJ. Adv. Carbohydr. Chem. Biochem. 1997, 52: 179 -
3c
Fugedi P.Garegg PJ.Lohn H.Norberg T. Glycoconjugate J. 1987, 4: 97 -
3d
Toshima K.Tatsuta K. Chem. Rev. 1993, 93: 1503 -
3e
Ferrier RJ.Furneaux RH. Methods Carbohydr. Chem. 1980, 8: 251 -
3f
Kartha KPR.Field RA. In Best Synthetic Methods: CarbohydratesOsborn HMI. Academic Press; Oxford: 2003. p.121-145 -
4a
Rosenbrook W.Riley DA.Lartey PA. Tetrahedron Lett. 1985, 26: 3 -
4b
Posner GH.Haines SR. Tetrahedron Lett. 1985, 26: 5 -
4c
Nicolaou KC.Dolle RE.Papahatjis DP.Randall LJ. J. Chem. Soc., Chem. Commun. 1984, 1155 -
5a
Kahne D.Walker S.Cheng Y.van Engen D. J. Am. Chem. Soc. 1989, 111: 6881 -
5b
Raghavan S.Kahne D.
J. Am. Chem. Soc. 1993, 115: 1580 -
5c
Yan L.Kahne D. J. Am. Chem. Soc. 1996, 118: 9239 -
5d
Crich D.Sun S.
J. Org. Chem. 1997, 62: 1198 -
6a
Brown DS.Ley SV.Vile S. Tetrahedron Lett. 1988, 29: 4873 -
6b
Brown DS.Ley SV.Vile S.Thompson M. Tetrahedron 1991, 47: 1329 -
6c
Chang GX.Lowary TL. Org. Lett. 2000, 2: 1505 -
6d
Vlahov IR.Vlahova PI.Linhardt RJ. J. Am. Chem. Soc. 1997, 119: 1480 -
7a
Khan SH.Hindsgaul O. In Molecular GlycobiologyFukuda M.Hindsgaul O. IRL; Oxford: 1994. p.206 -
7b
Norberg T. In Modern Methods in Carbohydrate Synthesis, Frontiers in Natural Product Research Series Vol. 1:Khan SH.O’Neill RA. Harwood Academic Publishers; Amsterdam: 1995. p.82-106 -
8a
Varki A. Glycobiology 1993, 3: 97 -
8b
Witczak ZJ. Curr. Med. Chem. 1999, 6: 165 - 9
Kanie O.Ito Y.Ogawa T. J. Am. Chem. Soc. 1994, 116: 12073 -
10a
Ferrier RJ.Hay RW.Vethaviyasar N. Carbohydr. Res. 1973, 27: 55 -
10b
Lemieux RU. Can. J. Chem. 1951, 29: 1079 -
10c
Lönn H. Carbohydr. Res. 1985, 139: 105 -
10d
Das SK.Roy N. Carbohydr. Res. 1996, 296: 1079 -
10e
Kihlberg JO.Leigh DA.Bundle DR. J. Org. Chem. 1990, 55: 2860 -
10f
Agnihotri G.Tiwari P.Misra AK. Carbohydr. Res. 2005, 340: 1393 -
10g
Tai CA.Kulkarni SS.Hung SC. J. Org. Chem. 2003, 68: 8719 -
10h
Weng SS.Lin YD.Chen CT. Org. Lett. 2006, 8: 5633 -
11a
Hanessian S.Guindon Y. Carbohydr. Res. 1980, 86: C3 -
11b
Pozsgay V.Jennings HJ. Tetrahedron Lett. 1987, 28: 1375 -
11c
Kameyama A.Ishida H.Kiso M.Hasegawa A. J. Carbohydr. Chem. 1991, 10: 549 -
12a
Mukherjee C.Tiwari P.Misra AK. Tetrahedron Lett. 2006, 47: 441 -
12b
Zhao X.Yu Z.Yan S.Wu S.Liu R.He W.Wang L. J. Org. Chem. 2005, 70: 7338 -
13a
Tiwari P.Agnihotri G.Misra AK. J. Carbohydr. Chem. 2005, 24: 723 -
13b
Ibatullin FM.Shabalin KA.Janis JV.Shavva AG. Tetrahedron Lett. 2003, 44: 7961 -
14a
Randell KD.Johnston BD.Brown PN.Pinto BM. Carbohydr. Res. 2000, 325: 253 -
14b
Jiaang W.-T.Chang M.-Y.Tseng P.-H.Chen S.-T. Tetrahedron Lett. 2000, 41: 3127 -
15a
Mehta S.Pinto BM. J. Org. Chem. 1993, 58: 3269 -
15b
Mehta S.Pinto BM. Tetrahedron Lett. 1991, 32: 4435 -
16a
Crich D.Suk D.-H.Sun S. Tetrahedron: Asymmetry 2003, 14: 2861 -
16b
Witczak ZJ.Whistler RL. Heterocycles 1982, 19: 1719 -
17a
Gerz M.Matter H.Kessler H. Angew. Chem., Int. Ed. Engl. 1993, 32: 269 -
17b
Aloui M.Chambers DJ.Cumpstey I.Fairbanks AJ.Redgrave AJ.Seward CMP. Chem. Eur. J. 2002, 8: 2608 -
18a
Debenham SD.Toone EJ. Tetrahedron: Asymmetry 2000, 11: 385 -
18b
Aravind A.Baskaran S. Tetrahedron Lett. 2005, 46: 743 -
18c
Aravind A.Mohanty SK.Pratap TV.Baskaran S. Tetrahedron Lett. 2005, 46: 2965 -
19a
Jain N.Kumar A.Chauhan S.Chauhan SMS. Tetrahedron 2005, 61: 1015 -
19b
Murugesan S.Linhardt RJ. Curr. Org. Synth. 2005, 2: 437 -
20a
Pakulski Z. Synthesis 2003, 2074 -
20b
Galan MC.Jouvin K.Alvarez-Dorta D. Carbohydr. Res. 2010, 345: 45 -
20c
Park T.-J.Weiwer M.Yuan X.Baytas SN.Munoz EV.Murugesan S.Linhardt RJ. Carbohydr. Res. 2007, 342: 614 -
20d
Rencurosi A.Lay L.Russo G.Caneva E.Poletti L. J. Org. Chem. 2005, 70: 7765 -
20e
Forsyth SA.MacGarlane DR.Thomson RJ.von Itzstein M. Chem. Commun. 2002, 714 -
20f
Zhang J.Ragauskas AJ. Carbohydr. Res. 2005, 340: 2812 - 21
Dasgupta F.Garegg PJ. Acta Chem. Scand. 1989, 43: 471 - 22
Mukherjee CM.Misra AK. J. Carbohydr. Chem. 2007, 26: 213 - 23
Martin-Lomas M.Khiar N.Garcia S.Koessler J.-L.Nieto PM.Rademacher TW. Chem. Eur. J. 2000, 6: 3608 - 24
Khiar N.Martin-Lomas M. J. Org. Chem. 1995, 60: 7017 - 25
Pozsgay V.Jennings HJ. J. Org. Chem. 1988, 53: 4042 - 26
Chowdhury US. Tetrahedron 1996, 52: 12775 - 27
Tropper FD.Andersson FO.Grand-Maitre C.Roy R. Synthesis 1991, 734 - 28
Tiwari P.Misra AK. Tetrahedron Lett. 2006, 47: 2345
References and Notes
Spectral data of products, which have
not been reported earlier, are presented below.
p
-Nitrophenyl
2,3,4,6-Tetra-
O
-acetyl-1-thio-β-
d
-glucopyranoside
(16)
Yellow solid; mp 180-182 ˚C; [α]D -32.7
(c 1.2, CHCl3). IR (KBr):
2923, 2368, 1753, 1344, 1220, 1042, 770 cm-¹. ¹H NMR
(200 MHz, CDCl3): δ = 8.16 (d, J = 8.9 Hz,
2 H), 7.59 (d, J = 8.8
Hz, 2 H), 5.28 (t, J = 9.2
Hz each, 1 H, H-3), 5.08 (t, J = 9.7
Hz each, 1 H, H-2), 5.04 (t, J = 9.6
Hz each, 1 H, H-4), 4.89 (d, J = 10.0
Hz, 1 H, H-1), 4.25-4.21 (m, 2 H, H-6a,b), 3.85-3.80
(m, 1 H, H-5), 2.10, 2.08, 2.04, 2.0 (4 s, 12 H, 4 COCH3). ¹³C
NMR (50 MHz, CDCl3): δ = 170.2, 169.9, 169.2,
169.0, 147.6, 141.6, 131.7 (2 C), 124.1 (2 C), 84.6, 76.6, 74.0,
70.0, 68.3, 62.2, 21.0, 20.9, 20.8 (2 C). ESI-MS: m/z = 508.1 [M + Na]+.
Anal. Calcd for C20H23NO11S (485.10):
C, 49.48; H, 4.78. Found: C, 49.25; H, 5.0.
Benzyl
2,3,4,6-Tetra-
O
-acetyl-1-seleno-β-
d
-gluco-pyranoside
(31)
Yellow oil; [α]D
²5 -30
(c 1.5, CHCl3). IR (neat):
2934, 1769, 1357, 1242, 1074, 764 cm-¹. ¹H
NMR (300 MHz, CDCl3):
δ = 7.40-7.21
(m, 5 H, ArH), 5.88 (d, J = 8.5
Hz, 1 H), 5.27 (t, J = 9.5
Hz each, 1 H), 5.06-4.89 (m, 2 H), 4.34-4.19 (m, 2
H), 3.90 (d, J = 11.1
Hz, 1 H), 3.83-3.67 (ABq, J = 12.0 Hz,
2 H), 2.08, 2.02, 1.99 (3 s, 12 H, 4 COCH
3). ¹³C
NMR (50 MHz, CDCl3): δ = 171.0, 170.8,
169.9 (2 C), 135.0-127.0 (ArC), 78.8, 76.3, 71.7, 71.2,
69.9, 68.6, 62.0, 26.6, 21.0, 20.9 (2 C). ESI-MS: m/z = 525.0 [M + Na]+.
Anal. Calcd for C21H26O9Se (502.07):
C, 50.31; H, 5.23. Found: C, 50.08; H, 5.50.
Benzyl 2,3,4,6-Tetra-
O
-acetyl-1-seleno-α-
d
-manno-pyranoside
(33)
Yellow oil; [α]D
²5 +126.8
(c 1.0, CHCl3). IR (neat):
2972, 2362, 1742, 1598, 1373, 1246, 1107, 1050, 977, 756 cm-¹. ¹H
NMR (200 MHz, CDCl3): δ = 7.28-7.09
(m, 5 H, ArH), 5.35 (br s, 1 H, H-2), 5.24 (br s, 1 H, H-1), 5.20-5.16
(m, 2 H, H-3 and H-4), 4.24-4.20 (m, 2 H, H-6ab),
3.91-3.85 (m, 1 H, H-5), 3.77-3.73 (ABq, J = 12.0 Hz,
2 H, CH2Ph), 2.07, 2.03, 1.98, 1.90 (4 s, 12 H, 4 COCH3). ¹³C
NMR (50 MHz, CDCl3): δ = 170.2, 169.4
(2 C), 169.3, 137.6, 128.6 (2 C), 128.3 (2 C), 126.8, 77.6, 71.4,
70.6, 69.7, 65.8, 61.8, 27.4, 20.5, 20.4, 20.3, 20.2. ESI-MS: m/z = 525 [M + Na]+.
ESI-MS: m/z = 525.0 [M + Na]+.
Anal. Calcd for C21H26O9Se (502.07):
C, 50.31; H, 5.23. Found: C, 50.09; H, 5.52.
Benzyl 2,3,4-Tri-
O
-acetyl-1-seleno-α-
l
-rhamno-pyranoside (36)
Yellow
oil; [α]D
²5 -114
(c 1.2, CHCl3). IR (neat):
2367, 1756, 1600, 1366, 1230, 955 cm-¹. ¹H
NMR (200 MHz, CDCl3): δ = 7.28-7.14
(m, 5 H, ArH), 5.34 (br s, 1 H, H-1), 5.32-5.30 (m, 1 H,
H-2), 5.18 (dd, J = 9.7,
3.0 Hz, 1 H, H-3), 5.04 (t, J = 9.7
Hz each, 1 H, H-4), 4.12-4.02 (m, 1 H, H-5), 3.83 (ABq, J = 12.2 Hz,
2 H, PhCH2), 2.08, 2.01, 1.93 (3 s, 9 H, 3 COCH3),
1.18 (d, J = 6.2
Hz, 1 H, CCH3). ESI-MS: m/z = 467.0 [M + Na]+.
Anal. Calcd for C19H24O7Se (444.07):
C, 51.47; H, 5.46. Found: C, 51.25; H, 5.70.
Benzyl 2,3,4,6-Tetra-
O
-acetyl-α-
d
-glucopyranosyl-(1→4)-2,3,6-tri-
O
-acetyl-1-seleno-β-
d
-glucopyranoside (39)
Yellow
oil; [α]D
²5 +51
(c 1.0, CHCl3). IR (neat):
3023, 1764, 1418, 1257, 1086, 769 cm-¹. ¹H
NMR (400 MHz, CDCl3):
δ = 7.32-7.20
(m, 5 H, ArH), 5.40-5.23 (m, 2 H), 5.18-5.09 (m,
1 H), 5.06-4.88 (m, 2 H), 4.86-4.76 (m, 1 H),
4.54-4.49 (m, 1 H), 4.46-4.38 (m, 1 H), 4.26-4.16
(m, 2 H), 4.06-3.82 (m, 5 H), 3.58-3.49 (m, 1
H), 2.13, 2.07, 1.99, 1.96, 1.95, 1.94 (6 s, 21 H, 7 COCH3).
ESI-MS: m/z = 813.1 [M + Na]+. Anal.
Calcd for C33H42O17Se (790.16):
C, 50.19; H, 5.36. Found: C, 50.0; H, 5.60.
Phenyl
2,3,4,6-Tetra-
O
-acetyl-β-
d
-galactopyranosyl-(1→4)-2,3,6-tri-
O
-acetyl-1-seleno-β-
d
-glucopyranoside (40)
Yellow
oil; [α]D
²5 +9
(c 1.0, CHCl3). IR (neat):
3036, 1790, 1432, 1276, 1094, 766 cm-¹. ¹H
NMR (400 MHz, CDCl3):
δ = 7.56-7.26
(m, 5 H, ArH), 5.30-5.28 (m, 1 H), 5.16 (t, J = 9.1 Hz
each, 1 H), 5.05 (dd, J = 7.3
Hz each, 1 H), 4.94-4.82 (m, 3 H), 4.51-4.46 (m,
1 H), 4.42 (d, J = 7.9
Hz, 1 H), 4.12-4.02 (m, 3 H), 3.85-3.81 (m, 1
H), 3.70 (t, J = 9.1
Hz each, 1 H), 3.62-3.56 (m, 1 H), 2.13, 2.07, 2.05, 2.01,
2.0, 1.94 (6 s, 21 H, 7 COCH3). ESI-MS: m/z = 799.1 [M + Na]+. Anal.
Calcd for C32H40O17Se (776.14):
C, 49.55; H, 5.20. Found: C, 49.32; H, 5.50.
Benzyl 2,3,4,6-Tetra-
O
-acetyl-β-
d
-galactopyranosyl-(1→4)-2,3,6-tri-
O
-acetyl-1-seleno-β-
d
-glucopyranoside (41)
Yellow
oil; [α]D
²5 +21
(c 1.0, CHCl3). IR (neat):
3023, 1767, 1424, 1281, 1089, 769 cm-¹. ¹H
NMR (400 MHz, CDCl3):
δ = 7.30-7.27
(m, 5 H, ArH), 5.40-5.28 (m, 2 H), 5.20-4.88 (m,
4 H), 4.54-4.44 (m, 2 H), 4.22-4.06 (m, 4 H),
4.02-3.86 (m, 2 H), 3.82-3.70 (m, 1 H), 3.56-3.48
(m, 1 H), 2.17, 2.15, 2.14, 2.06, 2.03, 2.0, 1.97 (7 s, 21 H, 7
COCH3). ESI-MS:
m/z = 813.1 [M + Na]+.
Anal. Calcd for C33H42O17Se (790.16):
C, 50.19; H, 5.36. Found: C, 50.0; H, 5.58.