benzyl 3-azido-2,3,6-trideoxy-4-O-propionyl-α-L-threo-hex-2-enopyranoside

Base Information

• Chemical Name: benzyl 3-azido-2,3,6-trideoxy-4-O-propionyl-α-L-threo-hex-2-enopyranoside
• CAS No.: 97389-96-3
• Molecular Formula: C₁₆H₁₉N₃O₄
• Molecular Weight: 317.345
• Mol file: 97389-96-3.mol

Synonyms:benzyl 3-azido-2,3,6-trideoxy-4-O-propionyl-α-L-threo-hex-2-enopyranoside

Chemical Property of benzyl 3-azido-2,3,6-trideoxy-4-O-propionyl-α-L-threo-hex-2-enopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 3-azido-2,3,6-trideoxy-4-O-propionyl-α-L-threo-hex-2-enopyranoside

There total 5 articles about benzyl 3-azido-2,3,6-trideoxy-4-O-propionyl-α-L-threo-hex-2-enopyranoside 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: 92.0%

cesium propionate (38869-24-8) + benzyl 3-azido-2,3,6-trideoxy-4-O-methanesulfonyl-α-L-erythro-hex-2-enopyranoside (97389-95-2) → benzyl 3-azido-2,3,6-trideoxy-4-O-propionyl-α-L-threo-hex-2-enopyranoside (97389-96-3)

Guidance literature:

In N,N-dimethyl-formamide; at 60 ℃; for 4h;

DOI:10.1016/0008-6215(85)85206-X

Reference yield:

benzyl 3-azido-2,3,6-trideoxy-α-L-glycero-hex-2-enopyranosid-4-ulose (97389-92-9) → benzyl 3-azido-2,3,6-trideoxy-4-O-propionyl-α-L-threo-hex-2-enopyranoside (97389-96-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 54 percent / NaBH₄ / ethanol / Ambient temperature

2: 84 percent / pyridine / 0 - 5 °C

3: 92 percent / dimethylformamide / 4 h / 60 °C

With sodium tetrahydroborate; In pyridine; ethanol; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(85)85206-X

Reference yield:

(2S,6R)-4-Azido-6-benzyloxy-2-methyl-3,6-dihydro-2H-pyran-3-ol → benzyl 3-azido-2,3,6-trideoxy-4-O-propionyl-α-L-threo-hex-2-enopyranoside (97389-96-3)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridinium dichromate, molecular sieves 4 Angstroem / CH₂Cl₂ / 12 h / Ambient temperature

2: 54 percent / NaBH₄ / ethanol / Ambient temperature

3: 84 percent / pyridine / 0 - 5 °C

4: 92 percent / dimethylformamide / 4 h / 60 °C

With sodium tetrahydroborate; dipyridinium dichromate; 4 A molecular sieve; In pyridine; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(85)85206-X

upstream raw materials:

cesium propionate

benzyl 3-azido-2,3,6-trideoxy-4-O-methanesulfonyl-α-L-erythro-hex-2-enopyranoside

benzyl 3-azido-2,3,6-trideoxy-α-L-glycero-hex-2-enopyranosid-4-ulose

benzyl 3-azido-2,3,6-trideoxy-α-L-erythro-hex-2-enopyranoside

Downstream raw materials:

benzyl 3-acetamido-2,3,6-trideoxy-4-O-propionyl-α-L-xylo-hexopyranoside

benzyl 3-acetamido-4-O-acetyl-2,3,6-trideoxy-α-L-ribo-hexopyranoside (benzyl N-acetyl-O-acetyl-α-L-ristosoaminide)