2-benzyl,3-hydroxy,4,6-benzylidene acetal-β-methyl galactopyranose

Base Information

• Chemical Name: 2-benzyl,3-hydroxy,4,6-benzylidene acetal-β-methyl galactopyranose
• CAS No.: 15038-71-8
• Molecular Formula: C₂₁H₂₄O₆
• Molecular Weight: 372.418
• Mol file: 15038-71-8.mol

Synonyms:2-benzyl,3-hydroxy,4,6-benzylidene acetal-β-methyl galactopyranose

Chemical Property of 2-benzyl,3-hydroxy,4,6-benzylidene acetal-β-methyl galactopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-benzyl,3-hydroxy,4,6-benzylidene acetal-β-methyl galactopyranose

There total 49 articles about 2-benzyl,3-hydroxy,4,6-benzylidene acetal-β-methyl galactopyranose 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: 87.0%

methyl 2-O-benzyl-4,6-O-benzylidene-3-O-p-methoxybenzyl-α-D-mannopyranoside (216758-63-3) → methyl 2-O-benzyl-(R)-4,6-O-benzylidene-α-D-mannopyranoside (15038-71-8,15384-58-4,23392-29-2,40653-23-4,57539-07-8,76375-66-1,81872-62-0,86363-45-3,90639-38-6,108739-91-9,116002-34-7,130192-76-6,131433-04-0,141115-75-5,78185-83-8)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile; at 0 ℃; for 2h;

DOI:10.1080/07328309808001894

Reference yield: 85.0%

methyl endo(phenyl)-2,3:4,6-di-O-benzylidene-α-D-mannopyranoside (73395-15-0) → (2R,4aR,6S,7S,8R,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (2774-19-8,14419-69-3,15887-67-9,23392-28-1,57539-08-9,61277-63-2,74410-51-8,76419-48-2,80734-73-2,86363-44-2,89301-79-1,94061-92-4,94062-87-0,108739-92-0,129706-93-0,143005-12-3,65877-21-6) + methyl 2-O-benzyl-(R)-4,6-O-benzylidene-α-D-mannopyranoside (15038-71-8,15384-58-4,23392-29-2,40653-23-4,57539-07-8,76375-66-1,81872-62-0,86363-45-3,90639-38-6,108739-91-9,116002-34-7,130192-76-6,131433-04-0,141115-75-5,78185-83-8)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -40 - 20 ℃;

DOI:10.1016/S0040-4020(02)01221-8

Reference yield: 85.0%

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) + benzyl bromide (100-39-0) → 2-benzyl,3-hydroxy,4,6-benzylidene acetal-β-methyl galactopyranose (15038-71-8)

Guidance literature:

methyl 4,6-O-benzylidene-β-D-galactopyranoside; With copper dichloride; (S,S)-2,6-bis(4-phenyl-2-oxazolinyl)pyridine; In acetonitrile; at 20 ℃; for 0.333333h;

benzyl bromide; With tetrabutylammomium bromide; silver(l) oxide; In acetonitrile; at 40 ℃; for 4h; regioselective reaction;

DOI:10.1002/adsc.202101121

upstream raw materials:

methyl 4,6-O-benzylidene-α-D-glucopyranoside

N,N-dimethyl(chlorophenylmethylene)ammonium chloride

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

benzyl bromide

Downstream raw materials:

methyl 2-O-benzyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-acetyl-α-D-rhamnopyranosyl)-α-D-glucopyranoside

(4aR,6S,7S,8aR)-7-Benzyloxy-6-methoxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one

methyl 2-O-benzyl-4-O-(2,3,4-tri-O-benzyl-β-L-fucopyranosyl)-α-D-glucopyranoside

methyl 2-O-benzyl-6-O-(2,3,4-tri-O-benzyl-β-L-fucopyranosyl)-α-D-glucopyranoside

Refernces

• 1、 Ren, Bo,Yan, Ningning,Gan, Lu. "Regioselective alkylation of carbohydrates and diols: A cheaper iron catalyst, new applications and mechanism". . p. 46257 - 46262. Retrieved 2017/10/11.
• 2、 Norberg, Oscar,Wu, Bin,Thota, Niranjan,Ge, Jian-Tao,Fauquet, Germain,Saur, Ann-Kathrin,Aastrup, Teodor,Dong, Hai,Yan, Mingdi,Ramstr?m, Olof. "Synthesis and binding affinity analysis of α1-2- and α1-6-O/S-linked dimannosides for the elucidation of sulfur in glycosidic bonds using quartz crystal microbalance sensors". supporting information. p. 35 - 42. Retrieved 2017/10/25.