| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1346067 | Tetrahedron: Asymmetry | 2012 | 6 Pages |
The total synthesis of acetyl derivatives of lyxo-(2R,3R,4R)-phytosphingosine and (−)-jaspine B using a Grignard reaction on sugar-imine and a Wittig reaction as the key steps.
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Benzyl benzyl((R)-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)allyl)carbamateC32H35NO6[α]D26=-49.2 (c 2.0, CHCl3)Source of chirality: d-GlucoseAbsolute configuration: (1R,3aR,5R,6S,6aR)
Benzyl benzyl((R)-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-hydroxyethyl)carbamateC31H35NO7[α]D26=-59.3 (c 1.5, CHCl3)Source of chirality: d-GlucoseAbsolute configuration: (1R,3aR,5R,6S,6aR)
(R)-3-Benzyl-4-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)oxazolidin-2-oneC24H27NO6[α]D26=-39.7 (c 1.0, CHCl3)Source of chirality: d-GlucoseAbsolute configuration: (4R,3aR,5R,6S,6aR)
(R)-3-Benzyl-4-((2R,3R,4R)-3-(benzyloxy)-4,5-dihydroxytetrahydrofuran-2-yl)oxazolidin-2-oneC21H23NO6[α]D26=-18.9 (c 1.0, CHCl3)Source of chirality: d-GlucoseAbsolute configuration: (41R,2R,3R,4R, 5R/S)
(R)-3-Benzyl-4-((1R,2R)-2-(benzyloxy)-1-hydroxyhexadec-3-enyl)oxazolidin-2-oneC33H47NO4[α]D26=-28.5 (c 1.0, CHCl3)Source of chirality: d-GlucoseAbsolute configuration: (4R,1R, 2R)
(2R,3R,4R,Z)-2-(Benzylamino)-4-(benzyloxy)octadec-5-ene-1,3-diolC33H52NO3[α]D26=-53.4 (c 1.0, CHCl3)Source of chirality: d-GlucoseAbsolute configuration: (2R,3R,4R,Z)
(2R,3R,4R,Z)-2-(Benzylamino)-4-(benzyloxy)octadec-5-ene-1,3-diolC26H47NO7[α]D26=+3.8 (c 0.62, CHCl3)Source of chirality: d-GlucoseAbsolute configuration: (2R,3R,4R)
tert-Butyl (2R,3R,4R)-1,3,4-trihydroxyoctadecan-2-ylcarbamateC23H47NO5[α]D26=+6.2 (c 1.5, CHCl3)Source of chirality: d-GlucoseAbsolute configuration: (2R,3R,4R)
tert-Butyl (3R,4R,5R)-4-hydroxy-5-tetradecyltetrahydrofuran-3-ylcarbamateC23H45NO5[α]D26=-7.1 (c 1.5, CHCl3)Source of chirality: d-GlucoseAbsolute configuration: (3R,4R,5R)
(2R,3R,4R)-4-Acetamido-2-tetradecyltetrahydrofuran-3-yl acetateC22H42NO2[α]D26=+26.8 (c 1.2, CHCl3)Source of chirality: d-GlucoseAbsolute configuration: (2R,3R,4R)
