phenyl 3-azido-2-O-benzyl-4,6-O-benzylidene-3-deoxy-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:phenyl 3-azido-2-O-benzyl-4,6-O-benzylidene-3-deoxy-1-thio-β-D-glucopyranoside
CAS No.:868258-57-5
Molecular Formula:C₂₆H₂₅N₃O₄S
Molecular Weight:475.568
Hs Code.:

Synonyms:phenyl 3-azido-2-O-benzyl-4,6-O-benzylidene-3-deoxy-1-thio-β-D-glucopyranoside

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Chemical Property of phenyl 3-azido-2-O-benzyl-4,6-O-benzylidene-3-deoxy-1-thio-β-D-glucopyranoside

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Technology Process of phenyl 3-azido-2-O-benzyl-4,6-O-benzylidene-3-deoxy-1-thio-β-D-glucopyranoside

There total 4 articles about phenyl 3-azido-2-O-benzyl-4,6-O-benzylidene-3-deoxy-1-thio-β-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: 96.0%

: 868258-56-4
phenyl 3-azido-4,6-O-benzylidene-3-deoxy-1-thio-β-D-glucopyranoside

: 100-39-0
benzyl bromide

: 868258-57-5
phenyl 3-azido-2-O-benzyl-4,6-O-benzylidene-3-deoxy-1-thio-β-D-glucopyranoside

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; Cooling with ice;
DOI:10.1021/acs.joc.5b00248

Reference yield:

: 205676-46-6
phenyl 3-azido-3-deoxy-1-thio-β-D-glucopyranoside

: 868258-57-5
phenyl 3-azido-2-O-benzyl-4,6-O-benzylidene-3-deoxy-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: TsOH*H₂O / dimethylformamide / 0.5 h / 60 °C

2: 0.92 g / NaH; TBAI / tetrahydrofuran

With tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/jm050368c

Reference yield:

: 139631-37-1
3-azido-1,3-dideoxy-1-(phenylsulfenyl)-2,4,6-tri-O-acetyl-β-D-gluco-pyranose

: 868258-57-5
phenyl 3-azido-2-O-benzyl-4,6-O-benzylidene-3-deoxy-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: MeONa / methanol / 1 h

2: TsOH*H₂O / dimethylformamide / 0.5 h / 60 °C

3: 0.92 g / NaH; TBAI / tetrahydrofuran

With sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1021/jm050368c