1,2,3,4-TETRABENZYL-BETA-D-GLUCOPYRANOSE

Base Information

• Chemical Name: 1,2,3,4-TETRABENZYL-BETA-D-GLUCOPYRANOSE
• CAS No.: 27851-29-2
• Molecular Formula: C34H36 O6
• Molecular Weight: 540.656
• Hs Code.: 2932999099
• Mol file: 27851-29-2.mol

Synonyms:Glucopyranoside,benzyl 2,3,4-tri-O-benzyl-, b-D- (8CI); Benzyl 2,3,4-tri-O-benzyl-b-D-glucopyranoside

Chemical Property of 1,2,3,4-TETRABENZYL-BETA-D-GLUCOPYRANOSE

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 100-102°C
• Boiling Point: 666.57°C at 760 mmHg
• PKA: 14.48±0.10(Predicted)
• Flash Point: 356.929°C
• PSA: 66.38000
• Density: 1.22±0.1 g/cm3 (20 ºC 760 Torr)
• LogP: 5.67660
• Storage Temp.: -20?C Freezer
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

98% ^*data from raw suppliers

Benzyl 2,3,4-Tri-O-benzyl-b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Benzyl 2,3,4-Tri-O-benzyl-D-glucopyranoside is an intermediate used in the synthesis of Isomaltose-13C (I821252), which is labelled Isomaltose. One of the main product of transformation of maltose into prebiotic isomaltooligosaccharides by novel α-glucosidase from Xantophyllomyces dendrorhous.

Technology Process of 1,2,3,4-TETRABENZYL-BETA-D-GLUCOPYRANOSE

There total 30 articles about 1,2,3,4-TETRABENZYL-BETA-D-GLUCOPYRANOSE 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: 97.0%

benzyl 6-O-acetyl-2,3,4-tri-O-benzyl-β-D-gluco-pyranoside (27851-30-5) → benzyl 2,3,4-tri-O-benzyl-D-glucopyranoside (27851-29-2)

Guidance literature:

With sodium methylate; In methanol; for 5h;

DOI:10.1016/j.carres.2005.02.013

Reference yield: 88.0%

(2R,3R,4S,5R,6R)-2,3,4,5-tetrakis(benzyloxy)-6-((trityloxy)methyl)tetrahydro-2H-pyran (27851-28-1,39687-22-4) → benzyl 2,3,4-tri-O-benzyl-D-glucopyranoside (27851-29-2)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; dichloromethane; at 20 ℃; for 6h;

DOI:10.1039/b212066f

Reference yield: 88.0%

benzyl 6-O-tert-butyldiphenylsilyl-2,3,4-tri-O-benzyl-β-D-glucopyranoside (291527-97-4) → benzyl 2,3,4-tri-O-benzyl-D-glucopyranoside (27851-29-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 9h;

DOI:10.1021/jo000220v

upstream raw materials:

benzyl 4,6-O-benzylidene-2,3-tri-O-benzyl-β-D-glucopyranoside

benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside

benzyl 6-O-acetyl-2,3,4-tri-O-benzyl-β-D-gluco-pyranoside

benzyl 2,3,4-tri-O-benzyl-6-O-(p-toluenesulfonyl)-β-D-glucopyranoside

Downstream raw materials:

benzyl O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside

benzyl O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside

benzyl O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-mannopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside

C₆₉H₇₁FO₁₂

Refernces

• 1、 -. "INHIBITORS OF MALARIAL AND PLASMODIUM FALCIPARUM HEXOSE TRANSPORTER AND USES THEREOF". Paragraph 00504; 00506. . Retrieved 2021/08/14.
• 2、 Saehlim, Natthiya,Athipornchai, Anan,Sirion, Uthaiwan,Saeeng, Rungnapha. "New class of alkynyl glycoside analogues as tyrosinase inhibitors". supporting information. . Retrieved 2020/06/01.