(3R,4R,5S,6S)-1-bromo-3-benzyloxy-4-hydroxy-5,6-(isopropylidenedioxy)cyclohex-1-ene

Base Information

Chemical Name:(3R,4R,5S,6S)-1-bromo-3-benzyloxy-4-hydroxy-5,6-(isopropylidenedioxy)cyclohex-1-ene
CAS No.:596834-79-6
Molecular Formula:C₁₆H₁₉BrO₄
Molecular Weight:355.228
Hs Code.:

Synonyms:(3R,4R,5S,6S)-1-bromo-3-benzyloxy-4-hydroxy-5,6-(isopropylidenedioxy)cyclohex-1-ene

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Chemical Property of (3R,4R,5S,6S)-1-bromo-3-benzyloxy-4-hydroxy-5,6-(isopropylidenedioxy)cyclohex-1-ene

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Technology Process of (3R,4R,5S,6S)-1-bromo-3-benzyloxy-4-hydroxy-5,6-(isopropylidenedioxy)cyclohex-1-ene

There total 1 articles about (3R,4R,5S,6S)-1-bromo-3-benzyloxy-4-hydroxy-5,6-(isopropylidenedioxy)cyclohex-1-ene 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: 63.0%

: 100-39-0
benzyl bromide

: 137501-12-3,130669-72-6
(3aS,4R,5R,7aS)-7-bromo-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo[d][1,3]dioxole-4,5-diol

: 596834-79-6
(3R,4R,5S,6S)-1-bromo-3-benzyloxy-4-hydroxy-5,6-(isopropylidenedioxy)cyclohex-1-ene

Guidance literature:: (3aS,4R,5R,7aS)-7-bromo-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo[d][1,3]dioxole-4,5-diol; With di(n-butyl)tin oxide; In toluene; for 5.5h; Heating;

benzyl bromide; With cesium fluoride; In N,N-dimethyl-formamide; at 20 ℃; for 18h;
DOI:10.1016/S0040-4020(03)00697-5

Reference yield:

: 596834-79-6
(3R,4R,5S,6S)-1-bromo-3-benzyloxy-4-hydroxy-5,6-(isopropylidenedioxy)cyclohex-1-ene

: (2S,3S,4aR,5S,6R,8aS)-5-Benzyloxy-7-bromo-6,8-difluoro-2,3-dimethoxy-2,3-dimethyl-2,3,4a,5,6,8a-hexahydro-benzo[1,4]dioxine

Guidance literature:: Multi-step reaction with 3 steps

1.1: CSA; trimethyl-orthoformate / 24 h / Heating

2.1: ClCOCOCl; DMSO / CH₂Cl₂ / -78 °C

2.2: 78 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: 30 percent / [CH₃OCH₂CH₂]NSF₃ / 72 h / 20 °C

With oxalyl dichloride; [CH₃OCH₂CH₂]NSF₃; camphor-10-sulfonic acid; dimethyl sulfoxide; trimethyl orthoformate; In dichloromethane; 2.1: Swern oxidation;
DOI:10.1016/S0040-4020(03)00697-5

Reference yield:

: 596834-79-6
(3R,4R,5S,6S)-1-bromo-3-benzyloxy-4-hydroxy-5,6-(isopropylidenedioxy)cyclohex-1-ene

: 596834-81-0
(2'S,3'S,4R,5R,6S)-2-bromo-4-O-benzyl-5-O,6-O-(2',3'-dimethoxybutane-2',3'-diyl)cyclohex-2-en-1-one-3,4,5-triol

Guidance literature:: Multi-step reaction with 2 steps

1.1: CSA; trimethyl-orthoformate / 24 h / Heating

2.1: ClCOCOCl; DMSO / CH₂Cl₂ / -78 °C

2.2: 78 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

With oxalyl dichloride; camphor-10-sulfonic acid; dimethyl sulfoxide; trimethyl orthoformate; In dichloromethane; 2.1: Swern oxidation;
DOI:10.1016/S0040-4020(03)00697-5