2,3,2',3',4',6'-Hexa-O-acetyl-1,6-anhydro-b-D-cellobiose

Base Information

• Chemical Name: 2,3,2',3',4',6'-Hexa-O-acetyl-1,6-anhydro-b-D-cellobiose
• CAS No.: 38631-27-5
• Molecular Formula: C₂₄H₃₂O₁₆
• Molecular Weight: 576.508
• Hs Code.: 2940000080
• Mol file: 38631-27-5.mol

Synonyms:2,3,2',3',4',6'-Hexa-O-acetyl-1,6-anhydro-b-D-cellobiose;1,6-Anhydro-beta-cellobiose hexaacetate;Cellobiosan hexaacetate

Chemical Property of 2,3,2',3',4',6'-Hexa-O-acetyl-1,6-anhydro-b-D-cellobiose

Chemical Property:

• PSA: 194.72000
• LogP: -0.92680

Purity/Quality:

98% ^*data from raw suppliers

CellobiosanHexaacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Cellobiosan hexaacetate is a cellobiosan (C254950) derivative and an enzyme substrate for β-?D-?glucosidase.

Technology Process of 2,3,2',3',4',6'-Hexa-O-acetyl-1,6-anhydro-b-D-cellobiose

There total 13 articles about 2,3,2',3',4',6'-Hexa-O-acetyl-1,6-anhydro-b-D-cellobiose 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:

acetic anhydride (108-24-7) + O4-(Tetra-O-acetyl-β-D-glucopyranosyl)-1,6-anhydro-β-D-mannopyranose (7225-54-9,67650-35-5) → O2,O3-Diacetyl-O4-(tetra-O-acetyl-β-D-glucopyranosyl)-1,6-anhydro-β-D-mannopyranose (2672-62-0,25878-57-3,28868-67-9,38631-27-5,56907-27-8,61117-14-4,61278-03-3,78215-48-2,139013-90-4)

Guidance literature:

With sodium acetate;

DOI:10.1021/ja01851a065

Reference yield:

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → O2,O3-Diacetyl-O4-(tetra-O-acetyl-β-D-galactopyranosyl)-1,6-anhydro-β-D-mannopyranose (2672-62-0,25878-57-3,28868-67-9,38631-27-5,56907-27-8,61117-14-4,61278-03-3,78215-48-2,139013-90-4)

Guidance literature:

With chloroform; iodine; silver(l) oxide; Erwaermen des Reaktionsprodukts mit wss. Essigsaeure und Erwaermen des danach isolierten Reaktionsprodukts mit Acetanhydrid und Natriumacetat;

DOI:10.1021/ja01260a031

Reference yield:

O2,O3-isopropylidene-O4-(tetra-O-acetyl-β-D-glucopyranosyl)-1,6-anhydro-β-D-mannopyranose (5346-69-0) → O2,O3-Diacetyl-O4-(tetra-O-acetyl-β-D-glucopyranosyl)-1,6-anhydro-β-D-mannopyranose (2672-62-0,25878-57-3,28868-67-9,38631-27-5,56907-27-8,61117-14-4,61278-03-3,78215-48-2,139013-90-4)

Guidance literature:

Multi-step reaction with 2 steps

1: aqueous acetic acid

2: pyridine

With pyridine; acetic acid;

DOI:10.1021/ja01851a065

upstream raw materials:

acetic anhydride

O⁴-(Tetra-O-acetyl-β-D-glucopyranosyl)-1,6-anhydro-β-D-mannopyranose

O²,O³-isopropylidene-O⁴-(tetra-O-acetyl-β-D-glucopyranosyl)-1,6-anhydro-β-D-mannopyranose

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Downstream raw materials:

1,6-anhydro-6'-O-trityl-β-cellobiose

1,6-anhydro-2,3-di-O-benzoyl-4-O-(2,3,4-tri-O-benzoyl-6-O-trityl-β-D-glucopyranosyl)-β-D-glucopyranose

1,6-anhydro-2,3-di-O-benzoyl-4-O-(2,3,4-tri-O-benzoyl-6-O-trityl-α-L-idopyranosyl)-β-D-glucopyranose

1,6-anhydro-2,3-di-O-benzyl-4-O-(2,3,4-tri-O-benzyl-6-O-trityl-β-D-glucopyranosyl)-β-D-glucopyranose

Refernces

• 1、 Tamura, Junichi,Schmidt, R. R.. "EFFECT OF PROTECTING GROUPS AND SOLVENTS IN ANOMERIC O-ALKYLATION OF MANNOPYRANOSE". . p. 895 - 912. Retrieved 2007/10/02.
• 2、 Kloosterman, M.,Dees, M. J.,Marel, G. A. van der,Boom, J. H. van. "Mild procedures for the synthesis of 1,6-anhydroaldohexopyranoses". . p. 116 - 119. Retrieved 2007/10/02.