2-(2'-O-benzyl-3',4',6'-tri-O-benzoyl-1-thio-α-D-glucopyranosyl)-benzoxazole

Base Information

• Chemical Name: 2-(2'-O-benzyl-3',4',6'-tri-O-benzoyl-1-thio-α-D-glucopyranosyl)-benzoxazole
• CAS No.: 957476-29-8
• Molecular Formula: C₄₁H₃₃NO₉S
• Molecular Weight: 715.78
• Mol file: 957476-29-8.mol

Synonyms:2-(2'-O-benzyl-3',4',6'-tri-O-benzoyl-1-thio-α-D-glucopyranosyl)-benzoxazole

Chemical Property of 2-(2'-O-benzyl-3',4',6'-tri-O-benzoyl-1-thio-α-D-glucopyranosyl)-benzoxazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 2-(2'-O-benzyl-3',4',6'-tri-O-benzoyl-1-thio-α-D-glucopyranosyl)-benzoxazole

There total 2 articles about 2-(2'-O-benzyl-3',4',6'-tri-O-benzoyl-1-thio-α-D-glucopyranosyl)-benzoxazole 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: 50.0%

2-sulfanyl-1,3-benzoxazole (2382-96-9,118090-08-7) + 1,3,4,6-tetra-O-benzoyl-2-O-benzyl-D-glucopyranose → 2-(2'-O-benzyl-3',4',6'-tri-O-benzoyl-1-thio-α-D-glucopyranosyl)-benzoxazole (957476-29-8)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; at 20 ℃; for 12h;

DOI:10.1021/ol701466u

Reference yield:

3,4,6-tri-O-benzoyl-2-O-benzyl-α-D-glucopyranosyl bromide (72946-46-4) → 2-(2'-O-benzyl-3',4',6'-tri-O-benzoyl-1-thio-α-D-glucopyranosyl)-benzoxazole (957476-29-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / Ag₂CO₃ / acetone; H₂O / 20 °C

2: 50 percent / Ph₃P; DEAD / CH₂Cl₂; tetrahydrofuran / 12 h / 20 °C

With triphenylphosphine; silver carbonate; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; water; acetone;

DOI:10.1021/ol701466u

Reference yield: 13.0%

2-(2'-O-benzyl-3',4',6'-tri-O-benzoyl-1-thio-α-D-glucopyranosyl)-benzoxazole (957476-29-8) + 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (4064-06-6) → 6-O-(2'-O-benzyl-3',4',6'-tri-O-benzoyl-α-D-glucopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside

Guidance literature:

With 5A molecular sieve; copper(II) bis(trifluoromethanesulfonate); at 20 ℃; for 14h;

DOI:10.1021/ol701466u

upstream raw materials:

2-sulfanyl-1,3-benzoxazole

3,4,6-tri-O-benzoyl-2-O-benzyl-α-D-glucopyranosyl bromide