methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside
• CAS No.: 64694-18-4
• Molecular Formula: C₆₂H₆₆O₁₁
• Molecular Weight: 987.199
• Mol file: 64694-18-4.mol

Synonyms:methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside

Chemical Property of methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside

There total 171 articles about methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-α-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%

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) + (2R,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-chlorotetrahydro-2H-pyran (92470-93-4) → methyl 4-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)(1→4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside (64694-18-4,77117-44-3,81307-79-1,82805-15-0,82805-16-1,82805-17-2,82805-18-3,84799-76-8,114817-97-9,114817-98-0,117894-99-2,123806-51-9,123877-32-7,117894-98-1)

Guidance literature:

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside; (2R,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-chlorotetrahydro-2H-pyran; With silver(l) oxide; In dichloromethane; at 0 ℃; for 0.166667h; Molecular sieve; Inert atmosphere;

With trifluorormethanesulfonic acid; In dichloromethane; at 0 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

DOI:10.1002/chem.201905576

Reference yield: 85.0%

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) + 2,3,4,6-tetra-O-benzyl-D-mannopyranose (4132-28-9,4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5) → methyl 4-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)(1→4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside (64694-18-4,77117-44-3,81307-79-1,82805-15-0,82805-16-1,82805-17-2,82805-18-3,84799-76-8,114817-97-9,114817-98-0,117894-99-2,123806-51-9,123877-32-7,117894-98-1)

Guidance literature:

2,3,4,6-tetra-O-benzyl-D-mannopyranose; With phthalic anhydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; acetonitrile; at 20 ℃; for 0.25h; Molecular sieve; Inert atmosphere;

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside; With di-tert-butylmethylpyridine; In dichloromethane; acetonitrile; at 0 ℃; for 0.25h; Inert atmosphere;

With trifluoromethylsulfonic anhydride; In dichloromethane; acetonitrile; at 0 - 20 ℃; stereoselective reaction; Inert atmosphere;

DOI:10.1021/ja710935z

Reference yield: 83.0%

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) + phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside (38184-10-0) → methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside (64694-18-4)

Guidance literature:

phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside; With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; N,N-dimethyl-formamide; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside; In dichloromethane; at 0 ℃; for 24h; Reagent/catalyst; stereoselective reaction; Inert atmosphere;

DOI:10.1021/jacs.8b00669

upstream raw materials:

1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose

methyl 2,3,6-tri-O-benzyl-4-O-trimethylsilyl-α-D-glucopyranoside

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside

1-deoxy-1-(S-ethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

Downstream raw materials:

debenzylated disaccharide

Refernces

• 1、 -. "HEPARANASE INHIBITORS FOR TREATMENT OF DIABETES". Paragraph 0302; 0321; 0328. . Retrieved 2021/07/10.
• 2、 Escopy, Samira,Singh, Yashapal,Stine, Keith J.,Demchenko, Alexei V.. "A Streamlined Regenerative Glycosylation Reaction: Direct, Acid-Free Activation of Thioglycosides". . p. 354 - 361. Retrieved 2020/12/02.