3-(2'-N-acetylamino-3',4'-di-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-1-propene

Base Information

• Chemical Name: 3-(2'-N-acetylamino-3',4'-di-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-1-propene
• CAS No.: 537031-57-5
• Molecular Formula: C₂₅H₃₁NO₅
• Molecular Weight: 425.525
• Mol file: 537031-57-5.mol

Synonyms:3-(2'-N-acetylamino-3',4'-di-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-1-propene

Chemical Property of 3-(2'-N-acetylamino-3',4'-di-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-1-propene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(2'-N-acetylamino-3',4'-di-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-1-propene

There total 2 articles about 3-(2'-N-acetylamino-3',4'-di-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-1-propene 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: 98.0%

3-(6'-O-acetyl-2'-N-acetylamino-3',4'-di-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-1-propene (537031-56-4) → 3-(2'-N-acetylamino-3',4'-di-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-1-propene (537031-57-5)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 20h;

DOI:10.1016/S0008-6215(02)00487-1

Reference yield:

3-(2'-N-acetylamino-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-1-propene (262286-48-6) → 3-(2'-N-acetylamino-3',4'-di-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-1-propene (537031-57-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / TMSOTf / CH₂Cl₂ / 1 h / -40 °C

2: 98 percent / NaOMe / methanol / 20 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; sodium methylate; In methanol; dichloromethane;

DOI:10.1016/S0008-6215(02)00487-1

Reference yield:

3-(2'-N-acetylamino-3',4'-di-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-1-propene (537031-57-5) → (2S,3S,4R,5S,6R)-5-Acetylamino-6-allyl-3,4-bis-benzyloxy-tetrahydro-pyran-2-carboxylic acid

Guidance literature:

With jones reagent; In acetone; at 20 ℃; for 48h;

DOI:10.1016/S0008-6215(02)00487-1

upstream raw materials:

3-(6'-O-acetyl-2'-N-acetylamino-3',4'-di-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-1-propene

3-(2'-N-acetylamino-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-1-propene

Downstream raw materials:

methyl 5-N-acetylamino-2,6-anhydro-3,4-di-O-benzyl-8,9-didehydro-5,7,8,9-tetradeoxy-D-glycero-L-gluco-nonuronate

3-(2'-N-acetylamino-6'-azido-3',4'-di-O-benzyl-2',6'-dideoxy-α-D-glucopyranosyl)-1-propene

methyl 5-N-acetylamino-2,6-anhydro-3,4-di-O-benzyl-5,7-dideoxy-D-glycero-L-gluco-octuronate

methyl 5-N-acetylamino-2,6-anhydro-8-azido-3,4-di-O-benzyl-5,7,8-trideoxy-D-glycero-L-gluco-octuronate