2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl chloride

Base Information

• Chemical Name: 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl chloride
• CAS No.: 65827-59-0
• Molecular Formula: C₂₉H₃₁ClO₆
• Molecular Weight: 511.015
• Mol file: 65827-59-0.mol

Synonyms:2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl chloride

Chemical Property of 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl chloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl chloride

There total 6 articles about 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl chloride 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: 91.7%

1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside (68567-54-4) → 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl chloride (65827-59-0)

Guidance literature:

With hydrogenchloride; In diethyl ether; for 3h; Ambient temperature;

Reference yield:

3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose (3254-16-8,4435-05-6,19189-54-9,29748-21-8,50801-29-1,64727-26-0,64727-27-1,65338-02-5,67672-68-8,78418-55-0,80877-03-8,103002-27-3,103002-29-5,132562-62-0) → 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl chloride (65827-59-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / KOH / tetrahydrofuran / 4 h / Heating

2: trimethylsilyl chloride / CH₂Cl₂ / 1 h / 0 °C

With potassium hydroxide; chloro-trimethyl-silane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo034213t

Reference yield:

D-Mannose pentaacetate (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5) → 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl chloride (65827-59-0)

Guidance literature:

Multi-step reaction with 4 steps

1: HBr / 6 h / 20 °C

2: 2,6-lutidine / CH₂Cl₂ / 12 h / 20 °C

3: 66 percent / KOH / tetrahydrofuran / 4 h / Heating

4: trimethylsilyl chloride / CH₂Cl₂ / 1 h / 0 °C

With 2,6-dimethylpyridine; potassium hydroxide; chloro-trimethyl-silane; hydrogen bromide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo034213t

upstream raw materials:

3,4,6-tri-O-benzyl-1,2-O-<1-(R)-methoxyethylidene>-β-D-mannopyranose

1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside

D-Mannose pentaacetate

3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose

Downstream raw materials:

methyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1<*>2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

benzyl O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-O->(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)>-2,4-di-O-benzyl-α-D-mannopyranoside

C₈₅H₉₀O₁₈

C₁₃₉H₁₄₆O₂₈