(2'S,3'S,3R,4R,5S,6S)-1-bromo-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-acetylcyclohex-1-ene-3,4,5,6-tetraol

Base Information

Chemical Name:(2'S,3'S,3R,4R,5S,6S)-1-bromo-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-acetylcyclohex-1-ene-3,4,5,6-tetraol
CAS No.:596834-82-1
Molecular Formula:C₂₁H₂₇BrO₇
Molecular Weight:471.345
Hs Code.:

Synonyms:(2'S,3'S,3R,4R,5S,6S)-1-bromo-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-acetylcyclohex-1-ene-3,4,5,6-tetraol

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Chemical Property of (2'S,3'S,3R,4R,5S,6S)-1-bromo-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-acetylcyclohex-1-ene-3,4,5,6-tetraol

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Technology Process of (2'S,3'S,3R,4R,5S,6S)-1-bromo-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-acetylcyclohex-1-ene-3,4,5,6-tetraol

There total 1 articles about (2'S,3'S,3R,4R,5S,6S)-1-bromo-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-acetylcyclohex-1-ene-3,4,5,6-tetraol 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:

: 108-24-7
acetic anhydride

: 596834-80-9
(2'S,3'S,3R,4R,5S)-1-bromo-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)cyclohex-1-ene-3,4,5,6-tetraol

: 596834-82-1
(2'S,3'S,3R,4R,5S,6S)-1-bromo-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-acetylcyclohex-1-ene-3,4,5,6-tetraol

Guidance literature:: With pyridine; dmap; In dichloromethane; at 20 ℃; for 6h;
DOI:10.1016/S0040-4020(03)00697-5

Reference yield: 97.0%

: 596834-82-1
(2'S,3'S,3R,4R,5S,6S)-1-bromo-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-acetylcyclohex-1-ene-3,4,5,6-tetraol

: 596834-80-9
(2'S,3'S,3R,4R,5S)-1-bromo-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)cyclohex-1-ene-3,4,5,6-tetraol

Guidance literature:: With potassium carbonate; In methanol; at 20 ℃; for 5.5h;
DOI:10.1016/S0040-4020(03)00697-5

Reference yield:

: 596834-82-1
(2'S,3'S,3R,4R,5S,6S)-1-bromo-3-O-benzyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-acetylcyclohex-1-ene-3,4,5,6-tetraol

: 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: 97 percent / K₂CO₃ / methanol / 5.5 h / 20 °C

2.1: ClCOCOCl; DMSO / CH₂Cl₂ / -78 °C

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

With oxalyl dichloride; potassium carbonate; dimethyl sulfoxide; In methanol; dichloromethane; 2.1: Swern oxidation;
DOI:10.1016/S0040-4020(03)00697-5