1,2,6-Tri-O-acetyl-3,4-di-O-benzyl-a-D-mannopyranose

Base Information

• Chemical Name: 1,2,6-Tri-O-acetyl-3,4-di-O-benzyl-a-D-mannopyranose
• CAS No.: 65827-57-8
• Molecular Formula: C26H30O9
• Molecular Weight: 486.51
• Mol file: 65827-57-8.mol

Synonyms:1,2,6-Tri-O-acetyl-3,4-di-O-benzyl-a-D-mannopyranose;3,4-Di-O-benzyl-1,2,6-tri-O-acetyl-α-D-mannopyranose;3,4-Bis-O-(phenylMethyl)-α-D-Mannopyranose Triacetate

Chemical Property of 1,2,6-Tri-O-acetyl-3,4-di-O-benzyl-a-D-mannopyranose

Chemical Property:

• Vapor Pressure: 4.29E-13mmHg at 25°C
• Melting Point: 73-75°C
• Boiling Point: 572°C at 760 mmHg
• Flash Point: 243°C
• PSA: 106.59000
• Density: 1.24g/cm³
• LogP: 2.94000
• Solubility.: Dichloromethane, Ether, Ethyl acetate, Methanol

Purity/Quality:

98%Min ^*data from raw suppliers

1,2,6-Tri-O-acetyl-3,4-di-O-benzyl-a-D-mannopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3,4-Di-O-benzyl-1,2,6-tri-O-acetyl-α-D-mannopyranose (cas# 65827-57-8) is a compound useful in organic synthesis.

Technology Process of 1,2,6-Tri-O-acetyl-3,4-di-O-benzyl-a-D-mannopyranose

There total 9 articles about 1,2,6-Tri-O-acetyl-3,4-di-O-benzyl-a-D-mannopyranose 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: 72.9%

3,4,6-tri-O-benzyl-1,2-O-(methoxyethylidene)-β-D-mannopyranose (16697-49-7) + acetic anhydride (108-24-7) → 1,2,6-tri-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranose (65827-57-8)

Guidance literature:

With sulfuric acid; In acetic acid; at 0 - 5 ℃; for 2h;

DOI:10.1016/S0008-6215(00)80753-3

Reference yield: 60.0%

acetic anhydride (108-24-7) + 3,4-di-O-benzyl-1,2-O-(1-methoxyethylidene)-6-O-trityl-β-D-mannopyramose (79218-91-0) → 1,2,6-tri-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranose (65827-57-8)

Guidance literature:

With sulfuric acid; In acetic acid; at 0 ℃; for 1.5h;

DOI:10.1016/S0008-6215(00)80753-3

Reference yield:

benzyl bromide (100-39-0) → 1,2,6-tri-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranose (65827-57-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / sodium hydride / dimethylformamide / 16 h / 20 °C

2: 60 percent / H₂SO₄ / acetic acid / 1.5 h / 0 °C

With sulfuric acid; sodium hydride; In acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)80753-3

upstream raw materials:

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

acetic anhydride

3,4-di-O-benzyl-1,2-O-(1-methoxyethylidene)-6-O-trityl-β-D-mannopyramose

(2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2,3-diol

Downstream raw materials:

Acetic acid (2R,3S,4S,5R,6R)-6-acetoxymethyl-4,5-bis-benzyloxy-2-ethylsulfanyl-tetrahydro-pyran-3-yl ester

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

2,6-di-O-acetyl-3,4-di-O-benzyl-β-D-mannopyranosyl bromide

2,6-di-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranosyl bromide

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