Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2003(2): 0247-0250
DOI: 10.1055/s-2003-36831
DOI: 10.1055/s-2003-36831
PAPER
© Georg Thieme Verlag Stuttgart · New YorkMolecular Iodine-Catalyzed Highly Stereoselective Synthesis of Sugar Acetylenes
Further Information
Received
21 August 2002
Publication Date:
22 January 2003 (online)
Publication History
Publication Date:
22 January 2003 (online)

Abstract
d-Glycals react smoothly with alkynylsilanes in the presence of a catalytic amount of molecular iodine under mild and convenient reaction conditions to afford the corresponding alkynyl sugars in excellent yields with high α-selectivity.
Key words
molecular iodine - alkynylsilanes - C-glycosides - sugar acetylenes
- 1a
Postema MHD. Tetrahedron 1992, 48: 8545 - 1b
Hanessian SC. In Total Synthesis of Natural Products: The Chiron Approach Pergamon Press; Oxford: 1984. - 2a
Lewis MD.Cha JK.Kishi Y. J. Am. Chem. Soc. 1982, 104: 4976 - 2b
Paterson L.Keown LE. Tetrahedron Lett. 1997, 38: 5727 - 2c
Horita K.Sakurai Y.Nagasawa M.Hachiya S.Yonemistu O. Synlett 1994, 43 - 3
Weatherman RV.Mortell KH.Chervenak M.Kiessling LL.Toone EJ. Biochemistry 1996, 35: 3619 - 4
Isobe M.Nishizawa R.Hosokawa S.Nishikawa T. Chem. Commun. 1998, 2665 - 5a
Hosokawa S.Isobe M. Synlett 1995, 1179 - 5b
Jiang Y.Ichikawa Y.Isobe M. Synlett 1995, 1185 - 5c
Hosokawa S.Isobe M. Synlett 1996, 351 - 6a
Tsukiyama T.Isobe M. Tetrahedron Lett. 1992, 33: 7911 - 6b
Huang G.Isobe M. Tetrahedron 2001, 57: 10241 - 6c
Tsukiyama T.Peters SC.Isobe M. Synlett 1993, 413 - 6d
Hosokawa S.Kirschbaum B.Isobe M. Tetrahedron Lett. 1998, 39: 1917 - 7a
Kartha KPR.Ballell L.Bilke J.McNeil M.Field RA. J. Chem. Soc,. Perkin Trans. 1 2001, 770 - 7b
Koreeda M.Houston TA.Shull BK.Klemke E.Tuinman RJ. Synlett 1995, 90 - 7c
Vaino AR.Szarek WA. Synlett 1995, 1157 - 7d
Lipshutz BH.Keith J. Tetrahedron Lett. 1998, 39: 2495 - 8a
Yadav JS.Reddy BVS.Hashim SR. J. Chem. Soc., Perkin Trans. 1 2000, 3025 - 8b
Yadav JS.Reddy BVS.Sabitha G.Reddy GSKK. Synthesis 2000, 1532 - 8c
Yadav JS.Reddy BVS.Rao CV.Rao KV. J. Chem. Soc., Perkin Trans. 1 2002, 1401