ethyl 4-azido-3-O-benzyl-4,6-dideoxy-1-thio-2-O-triflyl-β-D-mannopyranoside

Base Information

• Chemical Name: ethyl 4-azido-3-O-benzyl-4,6-dideoxy-1-thio-2-O-triflyl-β-D-mannopyranoside
• CAS No.: 861819-32-1
• Molecular Formula: C₁₆H₂₀F₃N₃O₅S₂
• Molecular Weight: 455.479
• Mol file: 861819-32-1.mol

Synonyms:ethyl 4-azido-3-O-benzyl-4,6-dideoxy-1-thio-2-O-triflyl-β-D-mannopyranoside

Chemical Property of ethyl 4-azido-3-O-benzyl-4,6-dideoxy-1-thio-2-O-triflyl-β-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 4-azido-3-O-benzyl-4,6-dideoxy-1-thio-2-O-triflyl-β-D-mannopyranoside

There total 3 articles about ethyl 4-azido-3-O-benzyl-4,6-dideoxy-1-thio-2-O-triflyl-β-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%

ethyl 4-azido-3-O-benzyl-4,6-dideoxy-1-thio-β-D-mannopyranoside (861819-31-0) + trifluoromethylsulfonic anhydride (358-23-6) → ethyl 4-azido-3-O-benzyl-4,6-dideoxy-1-thio-2-O-triflyl-β-D-mannopyranoside (861819-32-1)

Guidance literature:

In pyridine; dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1016/j.carres.2005.04.010

Reference yield:

1,2-Di-O-acetyl-4-azido-4,6-dideoxy-3-O-benzyl-α-D-mannopyranoside (117107-69-4) → ethyl 4-azido-3-O-benzyl-4,6-dideoxy-1-thio-2-O-triflyl-β-D-mannopyranoside (861819-32-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 6.9 percent / BF₃*Et₂O / CH₂Cl₂

2: 94 percent / NaOMe / methanol / 20 °C

3: 86 percent / CH₂Cl₂; pyridine / 0.5 h / 20 °C

With boron trifluoride diethyl etherate; sodium methylate; In pyridine; methanol; dichloromethane;

DOI:10.1016/j.carres.2005.04.010

Reference yield:

Ethyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-β-D-mannopyranoside (121804-01-1) → ethyl 4-azido-3-O-benzyl-4,6-dideoxy-1-thio-2-O-triflyl-β-D-mannopyranoside (861819-32-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / NaOMe / methanol / 20 °C

2: 86 percent / CH₂Cl₂; pyridine / 0.5 h / 20 °C

With sodium methylate; In pyridine; methanol; dichloromethane;

DOI:10.1016/j.carres.2005.04.010

upstream raw materials:

ethyl 4-azido-3-O-benzyl-4,6-dideoxy-1-thio-β-D-mannopyranoside

trifluoromethylsulfonic anhydride

1,2-Di-O-acetyl-4-azido-4,6-dideoxy-3-O-benzyl-α-D-mannopyranoside

Ethyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-β-D-mannopyranoside

Downstream raw materials:

ethyl 4-azido-3-O-benzyl-4,6-dideoxy-1-thio-β-D-glucopyranoside

ethyl 4-amino-3-O-benzyl-4,6-dideoxy-2-O-methyl-1-thio-β-D-glucopyranoside

ethyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-1-thio-β-D-glucopyranoside

ethyl 3-O-benzyl-4,6-dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-1-thio-β-D-glucopyranoside