benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside

Base Information

• Chemical Name: benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside
• CAS No.: 183953-29-9
• Molecular Formula: C₃₄H₃₄O₆
• Molecular Weight: 538.64
• Mol file: 183953-29-9.mol

Synonyms:benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside

Chemical Property of benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside

There total 8 articles about benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-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: 97.0%

benzyl bromide (100-39-0) + benzyl 4,6-O-benzylidene-β-D-glucopyranoside (30607-98-8,35905-28-3,40983-94-6,56341-65-2,57783-86-5,58006-32-9,72869-10-4,73366-72-0,79549-73-8,110850-30-1,113973-86-7,117895-05-3) → benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside (183953-29-9)

Guidance literature:

benzyl 4,6-O-benzylidene-β-D-glucopyranoside; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 0.5h; Inert atmosphere;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 48h; Inert atmosphere;

DOI:10.1021/jacs.6b06937

Reference yield:

benzyl bromide (100-39-0) + benzyl 4,6-O-benzylidene-β-D-glucopyranoside (30607-98-8,35905-28-3,40983-94-6,56341-65-2,57783-86-5,58006-32-9,72869-10-4,73366-72-0,79549-73-8,110850-30-1,113973-86-7,117895-05-3) → benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside (70144-60-4) + benzyl 2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside (86420-81-7) + benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside (183953-29-9)

Guidance literature:

With sodium hydroxide; tetra-(n-butyl)ammonium iodide; In dichloromethane; for 24h; Title compound not separated from byproducts; Ambient temperature;

DOI:10.1002/(SICI)1521-3897(199902)341:2<159::AID-PRAC159>3.0.CO;2-6

Reference yield:

(2R,3R,4S,5S,6R)-2-(benzyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (4304-12-5) → benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside (183953-29-9)

Guidance literature:

Multi-step reaction with 2 steps

1: benzaldehyde; zinc chloride

2: potassium hydroxide

With potassium hydroxide; benzaldehyde; zinc(II) chloride;

upstream raw materials:

benzyl bromide

benzyl 4,6-O-benzylidene-β-D-glucopyranoside

(2R,3R,4S,5S,6R)-2-(benzyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

D-glucose pentaacetate

Downstream raw materials:

benzyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside

L-1-deoxy-3,4,5,6-tetra-O-benzyl-myo-inositol

(2R,3R,4S,5S)-2,3,4,5-Tetrakis-benzyloxy-6-methylene-tetrahydro-pyran

D-2-deoxy-3,4,5,6-tetra-O-benzyl-myo-inositol

Refernces

• 1、 -. "TANNIN INHIBITORS OF HIV". . . Retrieved 2013/10/07.