(2S,3R,4E)-2-azido-1-tert-butyldimethylsilyloxy-3-(4-methoxybenzyl)-4-octadecen-3-ol

Base Information

Chemical Name:(2S,3R,4E)-2-azido-1-tert-butyldimethylsilyloxy-3-(4-methoxybenzyl)-4-octadecen-3-ol
CAS No.:152386-91-9
Molecular Formula:C₃₂H₅₇N₃O₃Si
Molecular Weight:559.908
Hs Code.:

Synonyms:(2S,3R,4E)-2-azido-1-tert-butyldimethylsilyloxy-3-(4-methoxybenzyl)-4-octadecen-3-ol

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Chemical Property of (2S,3R,4E)-2-azido-1-tert-butyldimethylsilyloxy-3-(4-methoxybenzyl)-4-octadecen-3-ol

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Technology Process of (2S,3R,4E)-2-azido-1-tert-butyldimethylsilyloxy-3-(4-methoxybenzyl)-4-octadecen-3-ol

There total 7 articles about (2S,3R,4E)-2-azido-1-tert-butyldimethylsilyloxy-3-(4-methoxybenzyl)-4-octadecen-3-ol 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:

: 152386-90-8
Methanesulfonic acid (E)-(1R,2R)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-heptadec-3-enyl ester

: 152386-91-9
(2S,3R,4E)-2-azido-1-tert-butyldimethylsilyloxy-3-(4-methoxybenzyl)-4-octadecen-3-ol

Guidance literature:: With sodium azide; 18-crown-6 ether; In N,N-dimethyl-formamide; at 75 ℃; for 20h; Yield given;
DOI:10.1016/S0040-4020(01)81834-2

Reference yield:

: 152386-84-0
(2R,3R)-2-O-(4-methoxybenzyl)-1,2,3,4-butanetetrol

: 152386-91-9
(2S,3R,4E)-2-azido-1-tert-butyldimethylsilyloxy-3-(4-methoxybenzyl)-4-octadecen-3-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 89 percent / p-TsOH / tetrahydrofuran

2: 1) DMSO, (COCl)2, 2) NEt₃ / 1) -78 deg C, 2 h, 2) -78 deg C, 30 min

3: 1) PhLi / 1) toluene/Et₂O, 0 deg C, 20 min, 2) THF, -30 deg C, 1 h

4: 93 percent / 2percent aq. H₂SO₄ / methanol / Ambient temperature

5: 91 percent / NEt₃, DMAP / CH₂Cl₂

6: NEt₃, DMAP / CH₂Cl₂ / 0 °C

7: NaN₃ / 18-crown-6 / dimethylformamide / 20 h / 75 °C

With dmap; sodium azide; oxalyl dichloride; sulfuric acid; toluene-4-sulfonic acid; dimethyl sulfoxide; phenyllithium; triethylamine; 18-crown-6 ether; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)81834-2

Reference yield:

: 152386-85-1
(1R,2S)-1-((R)-2,2-diethyl-1,3-dioxolan-4-yl)-2-((4-methoxybenzyl)oxy)ethan-1-ol

: 152386-91-9
(2S,3R,4E)-2-azido-1-tert-butyldimethylsilyloxy-3-(4-methoxybenzyl)-4-octadecen-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 1) DMSO, (COCl)2, 2) NEt₃ / 1) -78 deg C, 2 h, 2) -78 deg C, 30 min

2: 1) PhLi / 1) toluene/Et₂O, 0 deg C, 20 min, 2) THF, -30 deg C, 1 h

3: 93 percent / 2percent aq. H₂SO₄ / methanol / Ambient temperature

4: 91 percent / NEt₃, DMAP / CH₂Cl₂

5: NEt₃, DMAP / CH₂Cl₂ / 0 °C

6: NaN₃ / 18-crown-6 / dimethylformamide / 20 h / 75 °C

With dmap; sodium azide; oxalyl dichloride; sulfuric acid; dimethyl sulfoxide; phenyllithium; triethylamine; 18-crown-6 ether; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)81834-2