(Z)-(2R,3S,4S)-2,3,4-Tris-benzyloxy-5-benzyloxymethyl-6-bromo-hex-5-enal

Base Information

Chemical Name:(Z)-(2R,3S,4S)-2,3,4-Tris-benzyloxy-5-benzyloxymethyl-6-bromo-hex-5-enal
CAS No.:774599-18-7
Molecular Formula:C₃₅H₃₅BrO₅
Molecular Weight:615.564
Hs Code.:

Synonyms:(Z)-(2R,3S,4S)-2,3,4-Tris-benzyloxy-5-benzyloxymethyl-6-bromo-hex-5-enal

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Chemical Property of (Z)-(2R,3S,4S)-2,3,4-Tris-benzyloxy-5-benzyloxymethyl-6-bromo-hex-5-enal

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Technology Process of (Z)-(2R,3S,4S)-2,3,4-Tris-benzyloxy-5-benzyloxymethyl-6-bromo-hex-5-enal

There total 4 articles about (Z)-(2R,3S,4S)-2,3,4-Tris-benzyloxy-5-benzyloxymethyl-6-bromo-hex-5-enal 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: 98.0%

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

: 774599-18-7
(Z)-(2R,3S,4S)-2,3,4-Tris-benzyloxy-5-benzyloxymethyl-6-bromo-hex-5-enal

Guidance literature:: (Z)-(2S,3S,4S)-2,3,4-Tris-benzyloxy-5-benzyloxymethyl-6-bromo-hex-5-en-1-ol; With oxalyl dichloride; In dichloromethane; dimethyl sulfoxide; at -78 ℃; for 1h;

With triethylamine; at -78 ℃; for 0.416667h;
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

: 774599-18-7
(Z)-(2R,3S,4S)-2,3,4-Tris-benzyloxy-5-benzyloxymethyl-6-bromo-hex-5-enal

Guidance literature:: Multi-step reaction with 3 steps

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

2.1: 88 percent / TBAF / tetrahydrofuran / 1 h

3.1: oxalyl chloride / CH₂Cl₂; dimethylsulfoxide / 1 h / -78 °C

3.2: 98 percent / Et₃N / 0.42 h / -78 °C

With oxalyl dichloride; potassium tert-butylate; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; tert-butyl alcohol; 3.1: Swern oxidation;
DOI:10.1021/ol0490779

Reference yield:

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

: 774599-18-7
(Z)-(2R,3S,4S)-2,3,4-Tris-benzyloxy-5-benzyloxymethyl-6-bromo-hex-5-enal

Guidance literature:: Multi-step reaction with 2 steps

1.1: 88 percent / TBAF / tetrahydrofuran / 1 h

2.1: oxalyl chloride / CH₂Cl₂; dimethylsulfoxide / 1 h / -78 °C

2.2: 98 percent / Et₃N / 0.42 h / -78 °C

With oxalyl dichloride; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; 2.1: Swern oxidation;
DOI:10.1021/ol0490779