METHYL 4,6-O-BENZYLIDENE-BETA-D-GLUCOPYRANOSIDE

Base Information

• Chemical Name: METHYL 4,6-O-BENZYLIDENE-BETA-D-GLUCOPYRANOSIDE
• CAS No.: 14155-23-8
• Molecular Formula: C14H18 O6
• Molecular Weight: 282.293
• Hs Code.: 29389090
• Mol file: 14155-23-8.mol

Synonyms:Glucopyranoside,methyl 4,6-O-benzylidene-, b-D- (8CI); Pyrano[3,2-d]-1,3-dioxin, b-D-glucopyranoside deriv.; Methyl 4,6-O-benzylidene-b-D-glucopyranoside

Chemical Property of METHYL 4,6-O-BENZYLIDENE-BETA-D-GLUCOPYRANOSIDE

Chemical Property:

• Vapor Pressure: 9.45E-10mmHg at 25°C
• Melting Point: 198-200°C
• Refractive Index: 1.586
• Boiling Point: 473oC at 760 mmHg
• Flash Point: 239.8oC
• PSA: 77.38000
• Density: 1.36g/cm3
• LogP: 0.19370
• Storage Temp.: -20°C Freezer
• Solubility.: Methanol (Slightly), Water (Slightly, Heated)

Purity/Quality:

98%Min ^*data from raw suppliers

Methyl 4,6-O-Benzylidene-b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl 4,6-O-Benzylidene-β-D-glucopyranoside is used in the selective α-D-glucosylation of methyl 4,6-O-benzylidene-α- and -β-D-glucopyranosides.

Technology Process of METHYL 4,6-O-BENZYLIDENE-BETA-D-GLUCOPYRANOSIDE

There total 46 articles about METHYL 4,6-O-BENZYLIDENE-BETA-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: 98.0%

benzaldehyde dimethyl acetal (1125-88-8) + (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol (617-04-9) → methyl-4,6-O-phenylmethylene-α-D-mannopyranoside (3162-96-7,4148-58-7,4153-17-7,4288-93-1,5328-47-2,6988-39-2,13566-32-0,14155-23-8,27994-50-9,37093-57-5,37093-59-7,57701-27-6,59168-66-0,64552-06-3,65391-13-1,65391-14-2,65530-26-9,66512-65-0,71117-36-7,71117-37-8,71117-41-4,72904-85-9,74560-56-8,79549-74-9,86783-81-5,96093-51-5,98633-13-7,110415-35-5,110415-36-6,110850-29-8,124020-29-7,126924-12-7,129263-21-4,131433-03-9,145920-49-6,146863-04-9)

Guidance literature:

With camphor-10-sulfonic acid;

DOI:10.1021/ol030023t

Reference yield: 98.0%

benzaldehyde dimethyl acetal (1125-88-8) + methyl beta-D-galactopyranoside (1824-94-8) → methyl 4,6-O-benzylidene-β-D-galactopyranoside (3162-96-7,4148-58-7,4153-17-7,4288-93-1,5328-47-2,6988-39-2,13566-32-0,14155-23-8,27994-50-9,37093-57-5,37093-59-7,57701-27-6,59168-66-0,64552-06-3,65391-13-1,65391-14-2,65530-26-9,66512-65-0,71117-36-7,71117-37-8,71117-41-4,72904-85-9,74560-56-8,79549-74-9,86783-81-5,96093-51-5,98633-13-7,110415-35-5,110415-36-6,110850-29-8,124020-29-7,126924-12-7,129263-21-4,131433-03-9,145920-49-6,146863-04-9)

Guidance literature:

With sulfuric acid; In methanol; Heating;

DOI:10.1007/BF00581609

Reference yield: 96.0%

benzaldehyde dimethyl acetal (1125-88-8) + methyl beta-D-glucopyranoside (709-50-2) → methyl 4,6-O-benzylidene-β-D-glucopyranoside (14155-23-8)

Guidance literature:

With sulfuric acid; In methanol; Heating;

DOI:10.1007/BF00581609

upstream raw materials:

methyl β-D-galactopyranoside

benzaldehyde dimethyl acetal

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

benzaldehyde

Downstream raw materials:

Methyl-4,5-O-benzyliden-2,3-carbonato-α-D-mannopyranosid

methyl 4,6-O-benzylidene-2,3-di-O-methyl-α-D-mannopyranoside

methyl 4,6-O-benzylidene-α-D-galactopyranoside 2,3-bis(methanesulfonate)

(4aR)-6c-Methoxy-2c-phenyl-(4ar,9at)-hexahydro-[1,3]dioxino[5,4-e][1,4]dioxepin-7ξ,9ξ-diol

Refernces

• 1、 Joseph, Cosam C.,Zwanenburg, Binne,Chittenden, Gordon J. F.. "A rapid and facile preparation of methyl 4,6-O-benzylidene-α-D-glucopyranoside and some related compounds". . p. 493 - 497. Retrieved 2003.
• 2、 Maki, Yuta,Kajihara, Yasuhiro,Nomura, Kota,Okamoto, Ryo,Izumi, Masayuki,Mizutani, Yasuhisa. "Acceleration and deceleration factors on the hydrolysis reaction of 4,6-O-benzylidene acetal group". . p. 15849 - 15856. Retrieved 2021/01/18.
• 3、 Sauer, Maximilian M.,Jakob, Roman P.,Luber, Thomas,Canonica, Fabia,Navarra, Giulio,Ernst, Beat,Unverzagt, Carlo,Maier, Timm,Glockshuber, Rudi. "Binding of the Bacterial Adhesin FimH to Its Natural, Multivalent High-Mannose Type Glycan Targets". supporting information. p. 936 - 944. Retrieved 2019/01/11.