| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1347325 | Tetrahedron: Asymmetry | 2009 | 7 Pages |
An efficient and highly stereoselective approach to bicyclic aza sugars is described using Grignard reaction on an N-benzyl imine derived from 3-O-benzyl-1,2-O-isopropylidine-α-d-xylo-pentodialdofuranose, ring closing metathesis, and reductive cyclization as key steps.
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(S)-N-Benzyl-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)but-3-en-1-amineC25H31NO4[α]D30=-55.6 (c 0.52, CHCl3)Source of chirality: d-glucoseAbsolute configuration: (3aR,5R,6S,6aR)
(S)-N-Allyl-N-benzyl-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)but-3-en-1-amineC28H35NO4[α]D30=-38.6 (c 0.95, CHCl3)Source of chirality: d-glucoseAbsolute configuration: (3aR,5R,6S,6aR)
(S)-1-Benzyl-2-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-1,2,3,6-tetrahydropyridineC26H31NO4[α]D30=-25.2 (c 0.25, CHCl3)Source of chirality: d-glucoseAbsolute configuration: (3aR,5R,6S,6aR)
(1R,2R,3S,9aS)-Octahydro-1H-quinolizine-1,2,3-triyl triacetateC15H23NO6[α]D30=+8.4 (c 1.3, CHCl3)Source of chirality: d-glucoseAbsolute configuration: (1R,2R,3S,9aS)
(S)-N-Benzyl-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)pent-4-en-1-amineC26H33NO4[α]D30=-30.5 (c 0.85, CHCl3)Source of chirality: d-glucoseAbsolute configuration: (3aR,5R,6S,6aR)
(S)-N-allyl-N-benzyl-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)pent-4-en-1-amineC29H37NO4[α]D30=-57.6 (c 4.3, CHCl3)Source of chirality: d-glucoseAbsolute configuration: (3aR,5R,6S,6aR)
(S)-1-Benzyl-2-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2,3,4,7-tetrahydro-1H-azepineC27H33NO4[α]D30=-155.6 (c 0.25, CHCl3)Source of chirality: d-glucoseAbsolute configuration: (3aR,5R,6S,6aR)
(1R,2R,3S,10aS)-Decahydropyrido[1,2-a]azepine-1,2,3-triyl triacetateC16H25NO6[α]D30=+3.3 (c 0.9, CHCl3)Source of chirality: d-glucoseAbsolute configuration: (1R,2R,3S,10aS)
(R)-N-Benzyl-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)prop-2-en-1-amineC24H29NO4[α]D30=-15.1 (c 0.62, CHCl3)Source of chirality: d-glucoseAbsolute configuration: (3aR,5R,6S,6aR)
(R)-N-Allyl-N-benzyl-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)prop-2-en-1-amineC27H33NO4[α]D30=-16.8 (c 0.475, CHCl3)Source of chirality: d-glucoseAbsolute configuration: (3aR,5R,6S,6aR)
(R)-1-Benzyl-2-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2,5-dihydro-1H-pyrroleC25H29NO4[α]D30=-9.2 (c 1.2, CHCl3)Source of chirality: d-glucoseAbsolute configuration: (3aR,5R,6S,6aR)
6,7,8-Triacetyl, 1-deoxy, castanospermineC14H21NO6[α]D30=+38.3 (c 0.36, CHCl3)Source of chirality: d-glucoseAbsolute configuration: (6S,7R,8R,8aR)
(R)-N-Benzyl-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)pent-4-en-1-amineC26H33NO4[αD30=-34.5 (c 0.575, CHCl3)Source of chirality: d-glucoseAbsolute configuration: (3aR,5R,6S,6aR)
