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

Base Information

• Chemical Name: phenyl 3,6-di-O-acetyl-2,4-di-O-benzyl-1-thio-α-D-mannopyranoside
• CAS No.: 213998-08-4
• Molecular Formula: C₃₀H₃₂O₇S
• Molecular Weight: 536.646
• Mol file: 213998-08-4.mol

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

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

There total 9 articles about phenyl 3,6-di-O-acetyl-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: 85.0%

1,3,6-tri-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranose (80738-50-7) + thiophenol (108-98-5) → phenyl 3,6-di-O-acetyl-2,4-di-O-benzyl-1-thio-α-D-mannopyranoside (213998-08-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; for 2h;

DOI:10.1021/jo980294v

Reference yield: 81.0%

acetic anhydride (108-24-7) + phenyl 2,4-di-O-benzyl-1-phenylthio-α-D-mannopyranoside (210295-06-0) → phenyl 3,6-di-O-acetyl-2,4-di-O-benzyl-1-thio-α-D-mannopyranoside (213998-08-4)

Guidance literature:

With pyridine; at 0 - 20 ℃;

DOI:10.1002/chem.201405481

Reference yield:

methyl 2,4-di-O-benzyl-α-D-mannopyranoside (58341-67-6,67381-34-4,86172-91-0,86342-19-0,67381-29-7) → phenyl 3,6-di-O-acetyl-2,4-di-O-benzyl-1-thio-α-D-mannopyranoside (213998-08-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / H₂SO₄ / acetic acid / 4 h

2: 85 percent / Me₃SiOSO₂CF₃; 4-Angstroem molecular sieves / CH₂Cl₂ / 2 h

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sulfuric acid; In dichloromethane; acetic acid; 1: Acetylation / 2: Substitution;

DOI:10.1021/jo980294v

upstream raw materials:

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

thiophenol

acetic anhydride

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

Downstream raw materials:

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