(3E)-methyl-2-O-benzyl-4,6-O-benzylidene-3-bromomethylene-α-D-glucopyranoside

Base Information

Chemical Name:(3E)-methyl-2-O-benzyl-4,6-O-benzylidene-3-bromomethylene-α-D-glucopyranoside
CAS No.:1431845-83-8
Molecular Formula:C₂₂H₂₃BrO₅
Molecular Weight:447.326
Hs Code.:

Synonyms:(3E)-methyl-2-O-benzyl-4,6-O-benzylidene-3-bromomethylene-α-D-glucopyranoside

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Chemical Property of (3E)-methyl-2-O-benzyl-4,6-O-benzylidene-3-bromomethylene-α-D-glucopyranoside

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Technology Process of (3E)-methyl-2-O-benzyl-4,6-O-benzylidene-3-bromomethylene-α-D-glucopyranoside

There total 1 articles about (3E)-methyl-2-O-benzyl-4,6-O-benzylidene-3-bromomethylene-α-D-glucopyranoside 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: 51.0%

: 1034-49-7
(bromomethyl)triphenyl phosphonium bromide

: 109010-30-2
methyl 2-O-benzyl-4,6-O-benzylidene-α-D-ribo-hexopyranosid-3-ulose

: 1431845-83-8
(3E)-methyl-2-O-benzyl-4,6-O-benzylidene-3-bromomethylene-α-D-glucopyranoside

: 1431846-18-2
C₂₂H₂₃BrO₅

Guidance literature:: (bromomethyl)triphenyl phosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 1h; Inert atmosphere;

methyl 2-O-benzyl-4,6-O-benzylidene-α-D-ribo-hexopyranosid-3-ulose; In tetrahydrofuran; hexane; at 0 ℃; for 3.5h; Inert atmosphere;
DOI:10.1002/anie.201209697

Reference yield: 63.0%

: 1431845-83-8
(3E)-methyl-2-O-benzyl-4,6-O-benzylidene-3-bromomethylene-α-D-glucopyranoside

: 1-tributylstannylglucal

: 1431845-91-8
(3E)-methyl-(3,4,6-tri-O-benzylglucalyl)-(1?7C)-2-O-benzyl-4,6-O-benzylidene-3-methylene-α-D-glucopyranoside

Guidance literature:: With 1-methyl-pyrrolidin-2-one; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In acetonitrile; at 100 ℃; for 14.1667h; Inert atmosphere; Microwave irradiation;
DOI:10.1002/anie.201209697

Reference yield:

: 1431845-83-8
(3E)-methyl-2-O-benzyl-4,6-O-benzylidene-3-bromomethylene-α-D-glucopyranoside

: 1431845-99-6
methyl-(3,4,6-tri-O-benzylglucalyl)-(1?7C)-2-O-benzyl-4,6-O-benzylidene-3-methyl-α-D-allopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1-methyl-pyrrolidin-2-one / acetonitrile / 14.17 h / 100 °C / Inert atmosphere; Microwave irradiation

2: hydrogen / methanol; tetrahydrofuran / 5.5 h / 750.08 Torr / Inert atmosphere

With 1-methyl-pyrrolidin-2-one; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen; In tetrahydrofuran; methanol; acetonitrile; 1: |Stille Cross Coupling;
DOI:10.1002/anie.201209697