methyl 4,6-O-benzylidene-idopyranoside

Base Information

• Chemical Name: methyl 4,6-O-benzylidene-idopyranoside
• CAS No.: 74560-56-8
• Molecular Formula: C14H18 O6
• Molecular Weight: 282.293
• Mol file: 74560-56-8.mol

Synonyms:a-D-Idopyranoside, methyl4,6-O-(phenylmethylene)-, (S)-; Pyrano[3,2-d]-1,3-dioxin, a-D-idopyranoside deriv.

Chemical Property of methyl 4,6-O-benzylidene-idopyranoside

Chemical Property:

• Vapor Pressure: 9.45E-10mmHg at 25°C
• Boiling Point: 473°C at 760 mmHg
• Flash Point: 239.8°C
• PSA: 77.38000
• Density: 1.36g/cm³
• LogP: 0.19370

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4,6-O-benzylidene-idopyranoside

There total 39 articles about methyl 4,6-O-benzylidene-idopyranoside 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: 94.0%

methyl endo(phenyl)-2,3:4,6-di-O-benzylidene-α-D-mannopyranoside (73395-15-0) → 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 phosphomolybdic acid; silica gel; In dichloromethane; at 20 ℃; for 2h; chemoselective reaction;

DOI:10.1002/ejoc.200800963

upstream raw materials:

methyl 2,3-anhydro-4,6-dioxabenzylidene-α-D-talopyranose

methyl 2,3-anhydro-4,6-dioxabenzylidene-α-D-gulopyranose

(diethoxymethyl)benzene

methyl α-D-glucopyranoside

Downstream raw materials:

methyl 4,6-O-(S)-benzylidene-2,3-dimethyl-α-D-idopyranoside

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

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

(2S,4aR,6S,7S,8S,8aS)-8-Benzyloxymethoxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Refernces

• 1、 Fujiki, Katsumasa,Tanaka, Katsunori. "Exploration of the Fluoride Reactivity of Aryltrifluoroborate on Selective Cleavage of Diphenylmethylsilyl Groups". supporting information. p. 4616 - 4620. Retrieved 2020/07/06.
• 2、 Zhang, Wenhui,Wu, Qingquan,Oliver, Allen G.,Serianni, Anthony S.. "Conformational analysis of the disaccharide methyl a-d-mannopyranosyl-(1→3)-2-O-acetyl-β-D-manno-pyranoside monohydrate". . p. 610 - 615. Retrieved 2019/06/14.