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

Base Information

Chemical Name:(3E)-methyl-2-O-benzyl-4,6-O-benzylidene-3-bromomethylene-α-Dmannopyranoside
CAS No.:1431845-84-9
Molecular Formula:C₂₂H₂₃BrO₅
Molecular Weight:447.326
Hs Code.:

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

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

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

There total 1 articles about (3E)-methyl-2-O-benzyl-4,6-O-benzylidene-3-bromomethylene-α-Dmannopyranoside 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: 86.0%

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

: 141115-76-6
methyl 2-O-benzyl-4,6-O-(R)-benzylidene-α-D-arabinohexopyranosid-3-ulose

: 1431845-84-9
(3E)-methyl-2-O-benzyl-4,6-O-benzylidene-3-bromomethylene-α-Dmannopyranoside

Guidance literature:: (bromomethyl)triphenyl phosphonium bromide; With potassium tert-butylate; In tetrahydrofuran; at -78 ℃; for 1.5h; Inert atmosphere;

methyl 2-O-benzyl-4,6-O-(R)-benzylidene-α-D-arabinohexopyranosid-3-ulose; In tetrahydrofuran; at -78 - -25 ℃; for 2.16667h; Inert atmosphere;
DOI:10.1002/anie.201209697

Reference yield: 78.0%

: 1431845-84-9
(3E)-methyl-2-O-benzyl-4,6-O-benzylidene-3-bromomethylene-α-Dmannopyranoside

: 1-tributylstannylglucal

: 1431845-92-9
(3E)-methyl-(3,4,6-tri-O-benzylglucalyl)-(1?7C)-2-O-benzyl-4,6-O-benzylidene-3-methylene-α-D-mannopyranoside

Guidance literature:: With 1-methyl-pyrrolidin-2-one; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In acetonitrile; at 105 ℃; for 6.66667h; Inert atmosphere;
DOI:10.1002/anie.201209697

Reference yield:

: 1431845-84-9
(3E)-methyl-2-O-benzyl-4,6-O-benzylidene-3-bromomethylene-α-Dmannopyranoside

: 1431846-05-7
(3E)-methyl-(3,4,6-tri-O-benzyl-1-deoxy-β-D-glucopyranosyl)-(1?7C)-2-O-benzyl-4,6-O-benzylidene-3-methylene-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1-methyl-pyrrolidin-2-one / acetonitrile / 6.67 h / 105 °C / Inert atmosphere

2: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.33 h / -78 - 0 °C / Inert atmosphere

3: diisobutylaluminium hydride / hexane; toluene / 1 h / -78 - 20 °C / Inert atmosphere

With 1-methyl-pyrrolidin-2-one; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 3,3-dimethyldioxirane; diisobutylaluminium hydride; In hexane; dichloromethane; acetone; toluene; acetonitrile; 1: |Stille Cross Coupling;
DOI:10.1002/anie.201209697