3,4-di-O-benzyl-N-benzylcarboyl-1,2,6-trideoxy-1,5-imino-6-C-vinyl-D-iditol

Base Information

• Chemical Name: 3,4-di-O-benzyl-N-benzylcarboyl-1,2,6-trideoxy-1,5-imino-6-C-vinyl-D-iditol
• CAS No.: 1363300-70-2
• Molecular Formula: C₃₆H₃₇NO₅
• Molecular Weight: 563.693
• Mol file: 1363300-70-2.mol

Synonyms:3,4-di-O-benzyl-N-benzylcarboyl-1,2,6-trideoxy-1,5-imino-6-C-vinyl-D-iditol

Chemical Property of 3,4-di-O-benzyl-N-benzylcarboyl-1,2,6-trideoxy-1,5-imino-6-C-vinyl-D-iditol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4-di-O-benzyl-N-benzylcarboyl-1,2,6-trideoxy-1,5-imino-6-C-vinyl-D-iditol

There total 6 articles about 3,4-di-O-benzyl-N-benzylcarboyl-1,2,6-trideoxy-1,5-imino-6-C-vinyl-D-iditol 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: 78.0%

(2R,3S,4S,5R)-3,4,5-tris(benzyloxy)-1-(4-methoxybenzyl)-2-vinyl-piperidine (1363300-65-5) + benzyl chloroformate (501-53-1,94274-21-2) → 3,4-di-O-benzyl-N-benzylcarboyl-1,2,6-trideoxy-1,5-imino-6-C-vinyl-D-iditol (1363300-70-2)

Guidance literature:

In toluene; for 48h; Reflux;

DOI:10.1021/jm201633y

Reference yield:

C29H31NO5 + benzyl bromide (100-39-0) → 3,4-di-O-benzyl-N-benzylcarboyl-1,2,6-trideoxy-1,5-imino-6-C-vinyl-D-iditol (1363300-70-2)

Guidance literature:

C₂₉H₃₁NO₅; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

benzyl bromide; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1016/j.carres.2016.04.006

Reference yield:

2,3,4-tri-O-benzyl-1-deoxy-1-(4-methoxybenzylamino)-D-xylose (1222827-00-0) → 3,4-di-O-benzyl-N-benzylcarboyl-1,2,6-trideoxy-1,5-imino-6-C-vinyl-D-iditol (1363300-70-2)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran; diethyl ether / 2 h / 0 - 20 °C

2: pyridine; methanesulfonyl chloride / 16 h / 0 - 20 °C

3: toluene / 48 h / Reflux

With pyridine; methanesulfonyl chloride; In tetrahydrofuran; diethyl ether; toluene;

DOI:10.1021/jm201633y

upstream raw materials:

2,3,4-tri-O-benzyl-1-deoxy-1-(4-methoxybenzylamino)-D-xylose

(2R,3R,4S,5R)-2,3,4-tris(benzyloxy)-5-(4-methoxybenzylamino)-hept-6-en-1-ol

(2R,3S,4S,5R)-3,4,5-tris(benzyloxy)-1-(4-methoxybenzyl)-2-vinyl-piperidine

benzyl chloroformate