METHYL-2,6-DI-O-BENZOYL-ALPHA-D-GLUCOPYRANOSIDE

Base Information

• Chemical Name: METHYL-2,6-DI-O-BENZOYL-ALPHA-D-GLUCOPYRANOSIDE
• CAS No.: 26927-44-6
• Molecular Formula: C21H22 O8
• Molecular Weight: 402.401
• Mol file: 26927-44-6.mol

Synonyms:Methyl2,6-di-O-benzoyl-a-D-glucopyranoside

Chemical Property of METHYL-2,6-DI-O-BENZOYL-ALPHA-D-GLUCOPYRANOSIDE

Chemical Property:

• Melting Point: 141-142 °C
• Boiling Point: 568.8±50.0 °C(Predicted)
• PKA: 12.59±0.70(Predicted)
• PSA: 111.52000
• Density: 1.36±0.1 g/cm3(Predicted)
• LogP: 1.16210

Purity/Quality:

99% ^*data from raw suppliers

METHYL-2,6-DI-O-BENZOYL-ALPHA-D-GLUCOPYRANOSIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of METHYL-2,6-DI-O-BENZOYL-ALPHA-D-GLUCOPYRANOSIDE

There total 35 articles about METHYL-2,6-DI-O-BENZOYL-ALPHA-D-GLUCOPYRANOSIDE 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: 93.0%

methyl 2,6-di-O-benzoyl-3,4-di-O-benzyl-β-D-galactopyranoside (81561-90-2) → methyl 2,6-di-O-benzoyl-β-D-galactopyranoside (26927-44-6,29575-27-7,51996-13-5,88087-63-2,29575-26-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 30 - 40 ℃; for 72h;

DOI:10.1016/S0008-6215(00)81006-X

Reference yield: 91.0%

benzoyl chloride (98-88-4) + methyl-alpha-D-glucopyranoside (97-30-3) → methyl 2,3,6-tri-O-benzoyl-α-D-glucopyranoside (57784-06-2,6344-46-3) + methyl 2,6-di-O-benzoyl-α-D-glycopyranoside (26927-44-6)

Guidance literature:

methyl-alpha-D-glucopyranoside; With di(n-butyl)tin oxide; In toluene; benzene; Heating;

benzoyl chloride; In toluene; at 100 ℃; for 0.5h;

DOI:10.1016/S0040-4020(02)00661-0

Reference yield: 89.0%

methyl 3,4-di-O-(oxo(phenyl)acetyl)-2,6-di-O-benzoyl-α-D-glucopyranoside → methyl 2,6-di-O-benzoyl-α-D-glycopyranoside (26927-44-6)

Guidance literature:

With acetyl chloride; In methanol; at 20 ℃; Reagent/catalyst; Inert atmosphere;

DOI:10.1021/acs.joc.9b00126

upstream raw materials:

benzoyl chloride

methyl-alpha-D-glucopyranoside

methyl O²-benzoyl-α-D-glucoside

benzoic acid

Downstream raw materials:

(2R,3aS,4R,6S,7R,7aS)-7-Benzoyloxy-4-benzoyloxymethyl-6-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-carboxylic acid methyl ester

(2S,3aS,4R,6S,7R,7aS)-7-Benzoyloxy-4-benzoyloxymethyl-6-methoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-carboxylic acid methyl ester

Refernces

• 1、 Rasool, Javeed Ur,Kumar, Atul,Ali, Asif,Ahmed, Qazi Naveed. "Triethylamine-methanol mediated selective removal of oxophenylacetyl ester in saccharides". . p. 338 - 347. Retrieved 2021/01/29.
• 2、 Del Vigo, Enrique A.,Stortz, Carlos A.,Marino, Carla. "Experimental and theoretical study of the O3/O4 regioselectivity of glycosylation reactions of glucopyranosyl acceptors". . . Retrieved 2020/11/10.