(3S,4R,5R,6R,7S)-5-azido-3,4,7-tribenzyloxy-6,8-isopropylidenedioxyoct-1-en

Base Information

Chemical Name:(3S,4R,5R,6R,7S)-5-azido-3,4,7-tribenzyloxy-6,8-isopropylidenedioxyoct-1-en
CAS No.:272775-94-7
Molecular Formula:C₃₂H₃₇N₃O₅
Molecular Weight:543.663
Hs Code.:

Synonyms:(3S,4R,5R,6R,7S)-5-azido-3,4,7-tribenzyloxy-6,8-isopropylidenedioxyoct-1-en

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Chemical Property of (3S,4R,5R,6R,7S)-5-azido-3,4,7-tribenzyloxy-6,8-isopropylidenedioxyoct-1-en

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Technology Process of (3S,4R,5R,6R,7S)-5-azido-3,4,7-tribenzyloxy-6,8-isopropylidenedioxyoct-1-en

There total 22 articles about (3S,4R,5R,6R,7S)-5-azido-3,4,7-tribenzyloxy-6,8-isopropylidenedioxyoct-1-en 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: 79.0%

: 917-57-7
vinyllithium

: 100-39-0
benzyl bromide

: 330801-84-8
(2R,3S,4R,5S)-3-azido-2,5-dibenzyloxy-4,6-isopropylidenedioxy-hexanal

: 272775-94-7
(3S,4R,5R,6R,7S)-5-azido-3,4,7-tribenzyloxy-6,8-isopropylidenedioxyoct-1-en

Guidance literature:: vinyllithium; (2R,3S,4R,5S)-3-azido-2,5-dibenzyloxy-4,6-isopropylidenedioxy-hexanal; In diethyl ether; at -120 ℃;

With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

benzyl bromide; In N,N-dimethyl-formamide; at 0 ℃; for 4h; Further stages.;
DOI:10.1021/jo010925c

Reference yield:

: 100-39-0
benzyl bromide

: 272775-93-6
(3S,4R,5R,6R,7S)-5-azido-4,7-dibenzyloxy-6,8-isopropylidenedioxyoct-1-en-3-ol

: 272775-94-7
(3S,4R,5R,6R,7S)-5-azido-3,4,7-tribenzyloxy-6,8-isopropylidenedioxyoct-1-en

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃;
DOI:10.1021/ol005715l

Reference yield:

: 330801-83-7
(2S,3R,4S,5R)-4-azido-2,5-dibenzyloxy-hexan-1,3,6-triol

: 272775-94-7
(3S,4R,5R,6R,7S)-5-azido-3,4,7-tribenzyloxy-6,8-isopropylidenedioxyoct-1-en

Guidance literature:: Multi-step reaction with 3 steps

1.1: 83 percent / p-TsOH*H₂O / dimethylformamide / 3 h / 0 °C

2.1: trifluoroacetic acid; 1,3-dicyclohexylcarbodiimide; DMSO / benzene; pyridine / 2.5 h / 20 °C

3.1: diethyl ether / -120 °C

3.2: NaH / dimethylformamide / 0.5 h / 0 °C

3.3: 79 percent / dimethylformamide / 4 h / 0 °C

With toluene-4-sulfonic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In pyridine; diethyl ether; N,N-dimethyl-formamide; benzene; 2.1: Moffatt oxidation;
DOI:10.1021/jo010925c