Ethyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: Ethyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside
• CAS No.: 128643-88-9
• Molecular Formula: C₃₁H₃₆O₆S
• Molecular Weight: 536.689
• Mol file: 128643-88-9.mol

Synonyms:Ethyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside

Chemical Property of Ethyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Ethyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside

There total 2 articles about Ethyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-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: 97.0%

ethyl 2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside (39483-51-7,119645-03-3,128850-50-0,126461-54-9) + acetic anhydride (108-24-7) → Ethyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside (128643-88-9)

Guidance literature:

In pyridine;

DOI:10.1016/0008-6215(90)84108-7

Reference yield:

1,6-di-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose (4356-77-8,35094-65-6,61277-56-3,65556-30-1,78185-13-4,78185-15-6,109958-31-8,109958-33-0,113532-02-8,59433-13-5) + ethanethiol (75-08-1) → Ethyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside (128643-88-9) + 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside (171243-42-8)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 3h; optical yield given as %de; Inert atmosphere;

DOI:10.1016/j.carres.2009.06.037

Reference yield: 73.0%

p-methoxyphenyl (2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside + Ethyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside (128643-88-9) → p-methoxyphenyl (6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1→3)-(2-O-acetyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1→3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside + C64H69N3O17

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In diethyl ether; dichloromethane; at -40 ℃; for 1h; Molecular sieve; Inert atmosphere;

DOI:10.3762/bjoc.9.203

upstream raw materials:

ethyl 2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside

acetic anhydride

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

ethanethiol

Downstream raw materials:

Methyl 2-O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-4-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside

methyl 3-O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranoside

6-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose

methyl 2-O-benzyl-4,6-O-benzylidene-3-O-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosyluronate)-β-D-mannopyranoside