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

Base Information

• Chemical Name: 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
• CAS No.: 216776-90-8
• Molecular Formula: C₄₂H₄₇ClO₁₅S
• Molecular Weight: 859.345
• Mol file: 216776-90-8.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 2 articles about 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 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: 93.0%

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate (121238-27-5) + phenyl 2,4-di-O-benzyl-6-O-chloroacetyl-1-thio-α-D-mannopyranoside (216776-70-4) → 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)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane;

DOI:10.1080/07328309808001897

Reference yield:

phenyl 2,4-di-O-benzyl-1-phenylthio-α-D-mannopyranoside (210295-06-0) → 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)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / toluene; CH₂Cl₂ / 3 h / 60 °C

2: 93 percent / TfOH / CH₂Cl₂

With trifluorormethanesulfonic acid; In dichloromethane; toluene; 1: Acylation / 2: Substitution;

DOI:10.1080/07328309808001897

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

upstream raw materials:

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

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

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

Downstream raw materials:

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

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