ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-thio-α-D-mannopyranoside

Base Information

• Chemical Name: ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-thio-α-D-mannopyranoside
• CAS No.: 221678-96-2
• Molecular Formula: C₅₈H₆₄O₁₁S
• Molecular Weight: 969.206
• Mol file: 221678-96-2.mol

Synonyms:ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-thio-α-D-mannopyranoside

Chemical Property of ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-thio-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-thio-α-D-mannopyranoside

There total 5 articles about ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-thio-α-D-mannopyranoside 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: 75.0%

Ethyl 3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside (129750-23-8) + phenyl 2-O-acetyl-3,4,6-tri-O-Benzyl-1-seleno-α-D-mannopyranoside (152697-19-3) → ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-thio-α-D-mannopyranoside (221678-96-2)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; In diethyl ether; dichloromethane;

DOI:10.1039/a809798d

Reference yield:

3,4,6-tri-O-benzyl-1,2-O-(methoxyethylidene)-β-D-mannopyranose (16697-49-7) → ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-thio-α-D-mannopyranoside (221678-96-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 79 percent / 4 Angstroem molecular sieves / HgBr₂ / acetonitrile / 48 h / 20 °C

2: 91 percent / MeONa / methanol / 16 h / 20 °C

3: 71 percent / NIS; TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / -18 - 20 °C

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; mercury dibromide; In methanol; dichloromethane; acetonitrile; 1: Ring cleavage / 2: Deacetylation / 3: Etherification;

DOI:10.1039/b000873g

Reference yield:

ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside (130525-72-3) → ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-thio-α-D-mannopyranoside (221678-96-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / K₂CO₃; MeOH / 2 h

2: 75 percent / molecular sieves 4 Angstroem; NIS; TfOH / CH₂Cl₂; diethyl ether

With methanol; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; potassium carbonate; In diethyl ether; dichloromethane; 1: Deacetylation / 2: Glycosidation;

upstream raw materials:

Ethyl 3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

phenyl 2-O-acetyl-3,4,6-tri-O-Benzyl-1-seleno-α-D-mannopyranoside

3,4,6-tri-O-benzyl-1,2-O-(methoxyethylidene)-β-D-mannopyranose

ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

Downstream raw materials:

benzyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-α-D-mannopyranoside

8-Methoxycarbonyloctyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->3)-2,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-β-D-mannopyranoside