methyl 6-deoxy-6-(p-nitrophenylthio)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 6-deoxy-6-(p-nitrophenylthio)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• CAS No.: 126360-03-0
• Molecular Formula: C₃₄H₃₅NO₇S
• Molecular Weight: 601.72
• Mol file: 126360-03-0.mol

Synonyms:methyl 6-deoxy-6-(p-nitrophenylthio)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

Chemical Property of methyl 6-deoxy-6-(p-nitrophenylthio)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 6-deoxy-6-(p-nitrophenylthio)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

There total 3 articles about methyl 6-deoxy-6-(p-nitrophenylthio)-2,3,4-tri-O-benzyl-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: 86.0%

methyl 2,3,4-tri-O-benzyl-6-O-(4-methylbenzenesulfonyl)-α-D-glucopyranoside (114219-26-0) + para-nitrobenzenethiol (1849-36-1) → methyl 6-deoxy-6-(p-nitrophenylthio)-2,3,4-tri-O-benzyl-α-D-glucopyranoside (126360-03-0)

Guidance literature:

With sodium ethanolate; In ethanol; 1 h, 0 deg C and 24 h room t.;

DOI:10.1246/bcsj.62.3026

Reference yield:

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) → methyl 6-deoxy-6-(p-nitrophenylthio)-2,3,4-tri-O-benzyl-α-D-glucopyranoside (126360-03-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / pyridine / 24 h / Ambient temperature

2: 86 percent / NaOEt / ethanol / 1 h, 0 deg C and 24 h room t.

With pyridine; sodium ethanolate; In ethanol;

DOI:10.1246/bcsj.62.3026

Reference yield:

methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (7177-79-9,13035-24-0,29600-81-5,33164-02-2,51842-18-3,52526-59-7,78738-75-7,99212-27-8,101312-02-1,107795-23-3,108739-87-3,129170-92-9,13225-19-9) → methyl 6-deoxy-6-(p-nitrophenylthio)-2,3,4-tri-O-benzyl-α-D-glucopyranoside (126360-03-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) LiAlH₄ 2.) AlCl₃ / 1.) CH₂Cl₂, ether, reflux, 2.) CH₂Cl₂, ether 3 h, reflux

2: 96 percent / pyridine / 24 h / Ambient temperature

3: 86 percent / NaOEt / ethanol / 1 h, 0 deg C and 24 h room t.

With pyridine; lithium aluminium tetrahydride; aluminium trichloride; sodium ethanolate; In ethanol;

DOI:10.1246/bcsj.62.3026

upstream raw materials:

methyl 2,3,4-tri-O-benzyl-6-O-(4-methylbenzenesulfonyl)-α-D-glucopyranoside

para-nitrobenzenethiol

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

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