(2R,3R,4R)-5-azido-2,4-bis(benzyloxy)-2-(2-(benzyloxy)ethyl)pentane-1,3-diol

Base Information

Chemical Name:(2R,3R,4R)-5-azido-2,4-bis(benzyloxy)-2-(2-(benzyloxy)ethyl)pentane-1,3-diol
CAS No.:1271332-83-2
Molecular Formula:C₂₈H₃₃N₃O₅
Molecular Weight:491.587
Hs Code.:

Synonyms:(2R,3R,4R)-5-azido-2,4-bis(benzyloxy)-2-(2-(benzyloxy)ethyl)pentane-1,3-diol

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Chemical Property of (2R,3R,4R)-5-azido-2,4-bis(benzyloxy)-2-(2-(benzyloxy)ethyl)pentane-1,3-diol

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Technology Process of (2R,3R,4R)-5-azido-2,4-bis(benzyloxy)-2-(2-(benzyloxy)ethyl)pentane-1,3-diol

There total 10 articles about (2R,3R,4R)-5-azido-2,4-bis(benzyloxy)-2-(2-(benzyloxy)ethyl)pentane-1,3-diol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

: 1271332-80-9
(2R,3R,4R)-1-azido-2,4,6-tris(benzyloxy)-4-formylhexan-3-yl formate

: 1271332-83-2
(2R,3R,4R)-5-azido-2,4-bis(benzyloxy)-2-(2-(benzyloxy)ethyl)pentane-1,3-diol

Guidance literature:: (2R,3R,4R)-1-azido-2,4,6-tris(benzyloxy)-4-formylhexan-3-yl formate; With sodium tetrahydroborate; In methanol; at 0 - 20 ℃;

With ammonium chloride; In methanol; water;
DOI:10.1016/j.tetasy.2010.11.027

Reference yield:

: 1271332-66-1
(R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-6-(2-hydroxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-(trityloxy)ethanol

: 1271332-83-2
(2R,3R,4R)-5-azido-2,4-bis(benzyloxy)-2-(2-(benzyloxy)ethyl)pentane-1,3-diol

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C

1.2: 0 - 20 °C

2.1: silica supported perchloric acid / methanol / 3 h / 20 °C

3.1: dmap; triethylamine / dichloromethane / 1 h / 0 °C

4.1: sodium azide / N,N-dimethyl-formamide / 3 h / 120 °C

5.1: water; trifluoroacetic acid / 1 h / 20 °C

5.2: 0 - 20 °C

6.1: sodium tetrahydroborate / methanol / 0 - 20 °C

With dmap; sodium tetrahydroborate; sodium azide; silica supported perchloric acid; water; sodium hydride; triethylamine; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1016/j.tetasy.2010.11.027

Reference yield:

: 1271332-69-4
(3aR,5R,6R,6aR)-6-(benzyloxy)-5-((R)-1-(benzyloxy)-2-(trityloxy)ethyl)-6-(2-benzyloxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

: 1271332-83-2
(2R,3R,4R)-5-azido-2,4-bis(benzyloxy)-2-(2-(benzyloxy)ethyl)pentane-1,3-diol

Guidance literature:: Multi-step reaction with 5 steps

1.1: silica supported perchloric acid / methanol / 3 h / 20 °C

2.1: dmap; triethylamine / dichloromethane / 1 h / 0 °C

3.1: sodium azide / N,N-dimethyl-formamide / 3 h / 120 °C

4.1: water; trifluoroacetic acid / 1 h / 20 °C

4.2: 0 - 20 °C

5.1: sodium tetrahydroborate / methanol / 0 - 20 °C

With dmap; sodium tetrahydroborate; sodium azide; silica supported perchloric acid; water; triethylamine; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tetasy.2010.11.027