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

Base Information

• Chemical Name: ethyl 3,4,6-tri-O-acetyl-2-O-benzoyl-1-thio-α-D-mannopyranoside
• CAS No.: 515813-86-2
• Molecular Formula: C₂₁H₂₆O₉S
• Molecular Weight: 454.498
• Mol file: 515813-86-2.mol

Synonyms:ethyl 3,4,6-tri-O-acetyl-2-O-benzoyl-1-thio-α-D-mannopyranoside

Chemical Property of ethyl 3,4,6-tri-O-acetyl-2-O-benzoyl-1-thio-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 3,4,6-tri-O-acetyl-2-O-benzoyl-1-thio-α-D-mannopyranoside

There total 5 articles about ethyl 3,4,6-tri-O-acetyl-2-O-benzoyl-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: 65.0%

1,3,4,6-tetra-O-acetyl-2-O-benzoyl-α-D-mannopyranose (154092-35-0) + ethanethiol (75-08-1) → ethyl 3,4,6-tri-O-acetyl-2-O-benzoyl-1-thio-β-D-mannopyranoside + ethyl 3,4,6-tri-O-acetyl-2-O-benzoyl-1-thio-α-D-mannopyranoside (515813-86-2)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 5 - 7 ℃; for 24h;

DOI:10.1081/CAR-120016846

Reference yield: 58.0%

ethanethiol (75-08-1) + 1,3,4,6-tetra-O-acetyl-2-O-benzoyl-β-D-mannopyranose (515813-83-9) → ethyl 3,4,6-tri-O-acetyl-2-O-benzoyl-1-thio-β-D-mannopyranoside + ethyl 3,4,6-tri-O-acetyl-2-O-benzoyl-1-thio-α-D-mannopyranoside (515813-86-2)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 5 - 7 ℃; for 72h;

DOI:10.1081/CAR-120016846

Reference yield:

benzoyl chloride (98-88-4) → ethyl 3,4,6-tri-O-acetyl-2-O-benzoyl-1-thio-α-D-mannopyranoside (515813-86-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / pyridine / CH₂Cl₂ / 20 °C

2: 58 percent / BF₃-etherate / CH₂Cl₂ / 72 h / 5 - 7 °C

With pyridine; boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1081/CAR-120016846

upstream raw materials:

1,3,4,6-tetra-O-acetyl-2-O-benzoyl-α-D-mannopyranose

ethanethiol

1,3,4,6-tetra-O-acetyl-2-O-benzoyl-β-D-mannopyranose

benzoyl chloride

Downstream raw materials:

2-(trimethylsilyl)ethyl 3,4,6-tri-O-acetyl-2-O-benzoyl-α-D-mannopyranoside