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

Base Information

• Chemical Name: phenyl O-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1-3)-2,4-di-O-benzyl-1-thio-α-D-mannopyranoside
• CAS No.: 210295-20-8
• Molecular Formula: C₄₀H₄₆O₁₄S
• Molecular Weight: 782.863
• Mol file: 210295-20-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about phenyl O-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1-3)-2,4-di-O-benzyl-1-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: 86.0%

Chloro-acetic acid (2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-6-phenylsulfanyl-4-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester (216776-90-8) → phenyl O-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1-3)-2,4-di-O-benzyl-1-thio-α-D-mannopyranoside (210295-20-8)

Guidance literature:

With sodium hydrogencarbonate; thiourea; In ethanol; at 70 ℃; for 12h;

DOI:10.1080/07328309808001897

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate (121238-27-5) + phenyl 2,4-di-O-benzyl-1-phenylthio-α-D-mannopyranoside (210295-06-0) → Acetic acid (2R,3R,4S,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-((2R,3S,4S,5S,6R)-3,5-bis-benzyloxy-4-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-4-yl ester + phenyl O-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1-3)-2,4-di-O-benzyl-1-thio-α-D-mannopyranoside (210295-20-8) + C54H64O23S (210295-21-9)

Guidance literature:

With trifluorormethanesulfonic acid; AW 300 MS; In 1,2-dichloro-ethane; at -20 ℃; for 1h;

DOI:10.1016/S0008-6215(97)10001-5

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-mannopyranose (22860-22-6) → phenyl O-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1-3)-2,4-di-O-benzyl-1-thio-α-D-mannopyranoside (210295-20-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 35.1 g / DBU / CH₂Cl₂ / 2 h / 0 °C

2: 4 mg / TfOH, AW 300 MS / 1,2-dichloro-ethane / 1 h / -20 °C

With trifluorormethanesulfonic acid; AW 300 MS; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1016/S0008-6215(97)10001-5

upstream raw materials:

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate

phenyl 2,4-di-O-benzyl-1-phenylthio-α-D-mannopyranoside

Chloro-acetic acid (2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-6-phenylsulfanyl-4-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

phenyl 2,4-di-O-benzyl-6-O-chloroacetyl-1-thio-α-D-mannopyranoside

Downstream raw materials:

O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1-2)-O-(3,4,6-tri-O-acetyl-α-D-mannopyranosyl)-(1-6)-[O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1-3)]-2,4-di-O-benzyl-D-mannopyranosyl trichloroacetimidate