methyl 6-O-[2-S-(1'-acetyl-2'-methylethenyl)-3,4,6-tri-O-benzyl-2-thio-β-D-glucopyranosyl]-2,3,4-tri-O-benzyl-β-D-glucopyranoside

Base Information

• Chemical Name: methyl 6-O-[2-S-(1'-acetyl-2'-methylethenyl)-3,4,6-tri-O-benzyl-2-thio-β-D-glucopyranosyl]-2,3,4-tri-O-benzyl-β-D-glucopyranoside
• CAS No.: 354797-81-2
• Molecular Formula: C₆₀H₆₆O₁₁S
• Molecular Weight: 995.243
• Mol file: 354797-81-2.mol

Synonyms:methyl 6-O-[2-S-(1'-acetyl-2'-methylethenyl)-3,4,6-tri-O-benzyl-2-thio-β-D-glucopyranosyl]-2,3,4-tri-O-benzyl-β-D-glucopyranoside

Chemical Property of methyl 6-O-[2-S-(1'-acetyl-2'-methylethenyl)-3,4,6-tri-O-benzyl-2-thio-β-D-glucopyranosyl]-2,3,4-tri-O-benzyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 6-O-[2-S-(1'-acetyl-2'-methylethenyl)-3,4,6-tri-O-benzyl-2-thio-β-D-glucopyranosyl]-2,3,4-tri-O-benzyl-β-D-glucopyranoside

There total 4 articles about methyl 6-O-[2-S-(1'-acetyl-2'-methylethenyl)-3,4,6-tri-O-benzyl-2-thio-β-D-glucopyranosyl]-2,3,4-tri-O-benzyl-β-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: 58.0%

methyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside (4356-80-3,34212-64-1,40653-32-5,53008-65-4,55094-38-7,68027-27-0,73111-53-2,128184-63-4,138794-99-7,641635-63-4) + Acetic acid 1-((4aR,6R,7R,8S,8aR)-7,8-bis-benzyloxy-6-benzyloxymethyl-3-methyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalen-2-yl)-ethyl ester (196078-43-0) → methyl 6-O-[2-S-(1'-acetyl-2'-methylethenyl)-3,4,6-tri-O-benzyl-2-thio-β-D-glucopyranosyl]-2,3,4-tri-O-benzyl-β-D-glucopyranoside (354797-81-2)

Guidance literature:

With methyl trifluoromethanesulfonate; In nitromethane; for 0.833333h; Ambient temperature;

DOI:10.1039/a705338j

Reference yield: 38.0%

methyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside (4356-80-3,34212-64-1,40653-32-5,53008-65-4,55094-38-7,68027-27-0,73111-53-2,128184-63-4,138794-99-7,641635-63-4) + [1-((4aR,6R,7R,8S,8aR)-7,8-Bis-benzyloxy-6-benzyloxymethyl-3-methyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalen-2-yl)-ethoxy]-tert-butyl-dimethyl-silane (354797-82-3) → methyl 6-O-[2-S-(1'-acetyl-2'-methylethenyl)-3,4,6-tri-O-benzyl-2-thio-β-D-glucopyranosyl]-2,3,4-tri-O-benzyl-β-D-glucopyranoside (354797-81-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 0.25h;

DOI:10.1002/1099-0690(200106)2001:11<2083::AID-EJOC2083>3.0.CO;2-T

Reference yield:

1-O,2-S-(2-acetyl-1-methyl-1,2-ethenediyl)-3,4,6-tri-O-benzyl-2-thio-α-D-glucopyranose (152420-91-2) → methyl 6-O-[2-S-(1'-acetyl-2'-methylethenyl)-3,4,6-tri-O-benzyl-2-thio-β-D-glucopyranosyl]-2,3,4-tri-O-benzyl-β-D-glucopyranoside (354797-81-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / LiAlH / tetrahydrofuran / 0.5 h / 0 °C

2: 97 percent / DMAP; pyridine / CH₂Cl₂ / 15 h

3: 58 percent / MeOTf / nitromethane / 0.08 h / 20 °C

With pyridine; dmap; methyl trifluoromethanesulfonate; In tetrahydrofuran; nitromethane; dichloromethane;

DOI:10.1002/1099-0690(200106)2001:11<2083::AID-EJOC2083>3.0.CO;2-T

upstream raw materials:

methyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside

Acetic acid 1-((4aR,6R,7R,8S,8aR)-7,8-bis-benzyloxy-6-benzyloxymethyl-3-methyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalen-2-yl)-ethyl ester

[1-((4aR,6R,7R,8S,8aR)-7,8-Bis-benzyloxy-6-benzyloxymethyl-3-methyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalen-2-yl)-ethoxy]-tert-butyl-dimethyl-silane

1-O,2-S-(2-acetyl-1-methyl-1,2-ethenediyl)-3,4,6-tri-O-benzyl-2-thio-α-D-glucopyranose