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

Base Information

• Chemical Name: 1,4,6-Tri-O-acetyl-a-D-mannopyranose 2,3-Carbonate
• CAS No.: 53958-20-6
• Molecular Formula: C13H16O10
• Molecular Weight: 332.26
• Mol file: 53958-20-6.mol

Synonyms:1,4,6-Tri-O-acetyl-2,3-O-carbonyl-a-D-mannopyranose;2,3-O-Carbonyl-1,4,6-tri-O-acetyl-α-D-mannopyranose;1,4,6-Tri-O-acetyl-α-D-mannopyranose 2,3-Carbonate

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

Chemical Property:

• Melting Point: 115-117°C
• Boiling Point: 487.5±45.0 °C(Predicted)
• PSA: 123.66000
• Density: 1.42±0.1 g/cm3(Predicted)
• LogP: -0.32680

Purity/Quality:

98%Min ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 1,4,6-Tri-O-acetyl-a-D-mannopyranose 2,3-Carbonate is used for the synthesis of -mannosides 1,4,6-Tri-O-acetyl-α-D-mannopyranose 2,3-Carbonate (cas# 53958-20-6) is a compound useful in organic synthesis.

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

There total 5 articles about 1,4,6-Tri-O-acetyl-a-D-mannopyranose 2,3-Carbonate 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:

methyl 4,6-O-isopropylidene-α-D-mannopyranoside (63167-67-9) → 1,4,6-tri-O-acetyl-2,3-O-carbonyl-α-D-mannopyranose (53958-20-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / triethylamine / benzene; dioxane / 4 h / 0 °C

2: 1.) 90percent trifluoroacetic acid; 2.) sulphuric acid / 1.) ethanol, chloroform, 10 min, room t.; 2.) 4 h, room t.

With sulfuric acid; triethylamine; trifluoroacetic acid; In 1,4-dioxane; benzene;

DOI:10.1016/S0008-6215(00)85552-4

Reference yield:

(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol (617-04-9) → 1,4,6-tri-O-acetyl-2,3-O-carbonyl-α-D-mannopyranose (53958-20-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent

2: 74 percent / triethylamine / benzene; dioxane / 4 h / 0 °C

3: 1.) 90percent trifluoroacetic acid; 2.) sulphuric acid / 1.) ethanol, chloroform, 10 min, room t.; 2.) 4 h, room t.

With sulfuric acid; triethylamine; trifluoroacetic acid; In 1,4-dioxane; benzene;

DOI:10.1016/S0008-6215(00)85552-4

Reference yield:

acetic anhydride (108-24-7) + methyl 2,3-O-carbonyl-4,6-O-isopropylidene-α-D-mannopyranoside (74948-73-5) → 1,4,6-tri-O-acetyl-2,3-O-carbonyl-α-D-mannopyranose (53958-20-6) + 1,4,6-tri-O-acetyl-2,3-O-carbonyl-β-D-mannopyranose (103559-62-2)

Guidance literature:

With sulfuric acid; trifluoroacetic acid; Yield given. Multistep reaction; 1.) ethanol, chloroform, 10 min, room t.; 2.) 4 h, room t.;

DOI:10.1016/S0008-6215(00)85552-4

upstream raw materials:

acetic anhydride

methyl 2,3-O-carbonyl-4,6-O-isopropylidene-α-D-mannopyranoside

methyl 4,6-O-isopropylidene-α-D-mannopyranoside

(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

Downstream raw materials:

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

Refernces