Divergent Synthesis of Aminocyclopentitol Analogues via Stereoselective Amination of Cyclic Polybenzyl Ether with Chlorosulfonyl Isocyanate

Abstract

The divergent synthesis of some novel aminocyclopentitol analogues was concisely achieved from readily available d-galactose via the highly diastereoselective amination of carbocyclic polybenzyl ether using chlorosulfonyl isocyanate, diastereoselective dihydroxylation, and epoxidation as the key steps.

Key words

amination - aminocyclopentitol - chlorosulfonyl isocyanate - divergent synthesis - ether

• References and Notes

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• 15 Characterization Data of 6 R_f = 0.26 (CH₂Cl₂–MeOH–EtOH–NH₄OH = 5:2:2:1); [α]²⁵ _D +38.96 (c 1.0, CHCl₃). ¹H NMR (300 MHz, CD₃OD): δ = 5.71 (d, J = 1.2 Hz, 1 H), 4.46 (d, J = 5.4 Hz, 1 H), 4.21–4.16 (m, 2 H), 3.83–3.77 (m, 2 H). ¹³C NMR (125 MHz, CD₃OD): δ = 146.9, 128.3, 79.2, 73.3, 61.2, 59.0. HRMS (EI): m/z calcd for C₆H₁₁NO₃ [M]⁺: 145.0739; found: 145.0742.
• 16 Characterization Data of 7 R_f = 0.17 (CH₂Cl₂–MeOH–EtOH–NH₄OH = 5:3:3:1); [α]²⁵ _D –36.8 (c 1.0, CHCl₃). ¹H NMR (300 MHz, D₂O): δ = 4.43–4.39 (m, 1 H), 4.25 (d, J = 8.7 Hz, 1 H), 4.00 (d, J = 4.8 Hz, 1 H), 3.82 (d, J = 12.3 Hz, 1 H), 3.63 (d, J = 12.0 Hz, 1 H), 3.62–3.57 (m, 1 H). ¹³C NMR (125 MHz, D₂O): δ = 81.4, 74.1, 73.7, 67.9, 62.4, 56.7. HRMS (EI): m/z calcd for C₆H₁₃NO₅ [M]⁺: 179.0794; found: 179.0795.
• 17 Characterization Data of 8 R_f = 0.23 (CH₂Cl₂–MeOH–EtOH–NH₄OH = 5:2:1:1). [α]²⁵ _D –42.8 (c 1.0, CHCl₃). ¹H NMR (300 MHz, D₂O): δ = 4.30–4.23 (m, 2 H), 3.87 (dd, J = 7.8, 5.4 Hz, 1 H), 3.77 (s, 1 H), 3.66 (d, J = 13.2 Hz, 1 H), 3.57 (d, J = 8.1 Hz, 1 H). ¹³C NMR (125 MHz, D₂O): δ = 74.8, 68.6, 66.2, 61.8, 57.9, 56.2. HRMS (EI): m/z calcd for C₆H₁₁NO₄ [M]⁺: 161.0688; found: 161.0689.