2,3,6-tri-O-benzyl-4-O-methanesulfonyl-1-phenylthio-β-D-galactopyranoside

Base Information

• Chemical Name: 2,3,6-tri-O-benzyl-4-O-methanesulfonyl-1-phenylthio-β-D-galactopyranoside
• CAS No.: 236115-69-8
• Molecular Formula: C₃₄H₃₆O₇S₂
• Molecular Weight: 620.788

Synonyms:2,3,6-tri-O-benzyl-4-O-methanesulfonyl-1-phenylthio-β-D-galactopyranoside

Chemical Property of 2,3,6-tri-O-benzyl-4-O-methanesulfonyl-1-phenylthio-β-D-galactopyranoside

Chemical Property:

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Technology Process of 2,3,6-tri-O-benzyl-4-O-methanesulfonyl-1-phenylthio-β-D-galactopyranoside

There total 2 articles about 2,3,6-tri-O-benzyl-4-O-methanesulfonyl-1-phenylthio-β-D-galactopyranoside 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: 73.0%

methanesulfonyl chloride (124-63-0) + phenyl 2,3,6-tri-O-benzyl-1-thio-β-D-galactopyranoside (144781-45-3) → 2,3,6-tri-O-benzyl-4-O-methanesulfonyl-1-phenylthio-β-D-galactopyranoside (236115-69-8)

Guidance literature:

With pyridine; at 0 - 20 ℃; for 7h;

DOI:10.1021/ja9910356

Reference yield:

phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside (87470-72-2) → 2,3,6-tri-O-benzyl-4-O-methanesulfonyl-1-phenylthio-β-D-galactopyranoside (236115-69-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / BH₃*Me₃N, AlCl₃ / tetrahydrofuran / Ambient temperature

2: 73 percent / pyridine / 7 h / 0 - 20 °C

With pyridine; aluminium trichloride; trimethylamine-borane; In tetrahydrofuran;

DOI:10.1021/ja9910356

Reference yield: 84.0%

2,3,6-tri-O-benzyl-4-O-methanesulfonyl-1-phenylthio-β-D-galactopyranoside (236115-69-8) → 4-azido-4-deoxy-2,3,6-tri-O-benzyl-1-phenylthio-β-D-glucopyranoside (236115-67-6)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 100 ℃; for 13h;

DOI:10.1021/ja9910356

upstream raw materials:

methanesulfonyl chloride

phenyl 2,3,6-tri-O-benzyl-1-thio-β-D-galactopyranoside

phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

Downstream raw materials:

4-azido-4-deoxy-2,3,6-tri-O-benzyl-1-phenylthio-β-D-glucopyranoside

4-O-(4-azido-4-deoxy-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-2-deoxystreptamine

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