Methyl 4,6-O-benzylidene-a-D-galactopyranoside

Base Information

• Chemical Name: Methyl 4,6-O-benzylidene-a-D-galactopyranoside
• CAS No.: 4288-93-1
• Molecular Formula: C14H18 O6
• Molecular Weight: 282.293
• European Community (EC) Number: 806-036-0
• Nikkaji Number: J418.660E
• Mol file: 4288-93-1.mol

Synonyms:Methyl 4,6-O-benzylidene-a-D-galactopyranoside;72904-85-9;METHYL-4,6-O-BENZYLIDEN-ALPHA-D-GALACTOPYRANOSIDE;4288-93-1;(4aR,6S,7R,8R,8aR)-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol;SCHEMBL5575995;MFCD08274512;AKOS015919191;Methyl4,6-O-benzylidene-a-D-galactopyranoside;W-203658;Methyl 4-O,6-O-benzylidene-alpha-D-galactopyranoside;Methyl-4,6-O-benzylidene-alpha-D-galactopyranoside, 95%

Chemical Property of Methyl 4,6-O-benzylidene-a-D-galactopyranoside

Chemical Property:

• Melting Point: 153-158°C
• Boiling Point: 473°Cat760mmHg
• Flash Point: 239.8°C
• PSA: 77.38000
• Density: 1.36g/cm³
• LogP: 0.19370
• Storage Temp.: ?20°C
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 282.11033829
• Heavy Atom Count: 20
• Complexity: 319

Purity/Quality:

98% ^*data from raw suppliers

Methyl-4,6-O-benzylidene-α-D-galactopyranoside 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(C(C2C(O1)COC(O2)C3=CC=CC=C3)O)O
• Isomeric SMILES: CO[C@@H]1[C@@H]([C@H]([C@@H]2[C@H](O1)COC(O2)C3=CC=CC=C3)O)O

Technology Process of Methyl 4,6-O-benzylidene-a-D-galactopyranoside

There total 43 articles about Methyl 4,6-O-benzylidene-a-D-galactopyranoside 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: 96.4%

benzaldehyde dimethyl acetal (1125-88-8) + methyl α-D-galactopyranoside (3396-99-4) → methyl 4,6-O-benzylidene-α-D-galactopyranoside (4288-93-1)

Guidance literature:

tetrafluoroboric acid; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.1016/0008-6215(85)85171-5

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 2-O-allyl-4,6-O-benzylidene-α-D-allopyranoside

(4aS,6R,7S,8R,8aS)-8-Allyloxy-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.