(Z)-(2S,3S,4S)-2,3,4-Tris-benzyloxy-5-benzyloxymethyl-6-bromo-hex-5-en-1-ol

Base Information

Chemical Name:(Z)-(2S,3S,4S)-2,3,4-Tris-benzyloxy-5-benzyloxymethyl-6-bromo-hex-5-en-1-ol
CAS No.:774599-33-6
Molecular Formula:C₃₅H₃₇BrO₅
Molecular Weight:617.58
Hs Code.:

Synonyms:(Z)-(2S,3S,4S)-2,3,4-Tris-benzyloxy-5-benzyloxymethyl-6-bromo-hex-5-en-1-ol

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Chemical Property of (Z)-(2S,3S,4S)-2,3,4-Tris-benzyloxy-5-benzyloxymethyl-6-bromo-hex-5-en-1-ol

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Technology Process of (Z)-(2S,3S,4S)-2,3,4-Tris-benzyloxy-5-benzyloxymethyl-6-bromo-hex-5-en-1-ol

There total 3 articles about (Z)-(2S,3S,4S)-2,3,4-Tris-benzyloxy-5-benzyloxymethyl-6-bromo-hex-5-en-1-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: 88.0%

: 774599-17-6
tert-Butyl-dimethyl-((Z)-(2S,3S,4S)-2,3,4-tris-benzyloxy-5-benzyloxymethyl-6-bromo-hex-5-enyloxy)-silane

: 774599-33-6
(Z)-(2S,3S,4S)-2,3,4-Tris-benzyloxy-5-benzyloxymethyl-6-bromo-hex-5-en-1-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1h;
DOI:10.1021/ol0490779

Reference yield:

: 774599-32-5
(3R,4R,5S)-1,3,4,5-Tetrakis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-hexan-2-one

: 774599-33-6
(Z)-(2S,3S,4S)-2,3,4-Tris-benzyloxy-5-benzyloxymethyl-6-bromo-hex-5-en-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1: potassium tert-butoxide / tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / -78 °C

2: 88 percent / TBAF / tetrahydrofuran / 1 h

With potassium tert-butylate; tetrabutyl ammonium fluoride; In tetrahydrofuran; tert-butyl alcohol;
DOI:10.1021/ol0490779

Reference yield:

: 158535-90-1
1,3,4,5-Tetra-O-benzyl-6-O-(tert-butyldimethylsilyl)-L-galactitol

: 774599-33-6
(Z)-(2S,3S,4S)-2,3,4-Tris-benzyloxy-5-benzyloxymethyl-6-bromo-hex-5-en-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: oxalyl chloride / CH₂Cl₂; dimethylsulfoxide / 2.5 h / -78 °C

1.2: 84 percent / Et₃N / 0.25 h / -78 °C

2.1: potassium tert-butoxide / tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / -78 °C

3.1: 88 percent / TBAF / tetrahydrofuran / 1 h

With oxalyl dichloride; potassium tert-butylate; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; tert-butyl alcohol; 1.1: Swern oxidation;
DOI:10.1021/ol0490779