2-acetamido-4,6-O-benzylidene-N-benzyloxycarbonyl-1,5-imino-1,2,5-trideoxy-D-glucitol

Base Information

• Chemical Name: 2-acetamido-4,6-O-benzylidene-N-benzyloxycarbonyl-1,5-imino-1,2,5-trideoxy-D-glucitol
• CAS No.: 175519-63-8
• Molecular Formula: C₂₃H₂₆N₂O₆
• Molecular Weight: 426.469
• Mol file: 175519-63-8.mol

Synonyms:2-acetamido-4,6-O-benzylidene-N-benzyloxycarbonyl-1,5-imino-1,2,5-trideoxy-D-glucitol

Chemical Property of 2-acetamido-4,6-O-benzylidene-N-benzyloxycarbonyl-1,5-imino-1,2,5-trideoxy-D-glucitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-acetamido-4,6-O-benzylidene-N-benzyloxycarbonyl-1,5-imino-1,2,5-trideoxy-D-glucitol

There total 8 articles about 2-acetamido-4,6-O-benzylidene-N-benzyloxycarbonyl-1,5-imino-1,2,5-trideoxy-D-glucitol 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: 100.0%

2-acetamido-4,6-O-benzylidene-1,5-(benzyloxycarbonyl)imino-3-O-tert-butyldimethylsilyl-1,2,5-trideoxy-D-glucitol (1356848-60-6) → 2-acetamido-4,6-O-benzylidene-N-benzyloxycarbonyl-1,5-imino-1,2,5-trideoxy-D-glucitol (175519-63-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1021/ml2002746

Reference yield:

C21H32N2O6Si → 2-acetamido-4,6-O-benzylidene-N-benzyloxycarbonyl-1,5-imino-1,2,5-trideoxy-D-glucitol (175519-63-8)

Guidance literature:

Multi-step reaction with 3 steps

1: dimethyl sulfide borane / tetrahydrofuran; dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere

2: pyridine / dichloromethane / 1 h / 20 °C / Inert atmosphere

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

With pyridine; tetrabutyl ammonium fluoride; dimethyl sulfide borane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ml2002746

Reference yield:

C21H34N2O4Si → 2-acetamido-4,6-O-benzylidene-N-benzyloxycarbonyl-1,5-imino-1,2,5-trideoxy-D-glucitol (175519-63-8)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / dichloromethane / 1 h / 20 °C / Inert atmosphere

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

With pyridine; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ml2002746

upstream raw materials:

acetic anhydride

2,3-Anhydro-4,6-O-(R-benzylidene)-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-mannitol

4,6-O-benzylidene-N-benzyloxycarbonyl-3-O-chloroacetyl-1,5-dideoxy-1,5-imino-D-glucitol

(2R,4aR,7S,8S,8aR)-8-(2-Chloro-acetoxy)-7-methanesulfonyloxy-2-phenyl-hexahydro-[1,3]dioxino[5,4-b]pyridine-5-carboxylic acid benzyl ester

Downstream raw materials:

(2R,4aR,7S,8R,8aR)-7-Acetylamino-2-phenyl-8-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-[1,3]dioxino[5,4-b]pyridine-5-carboxylic acid benzyl ester

(2R,3R,4R,5S)-5-Acetylamino-2-benzyloxymethyl-3-hydroxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-piperidine-1-carboxylic acid benzyl ester

N-{2-O-[2-acetamido-4,6-O-benzylidene-1,5-(benzyloxycarbonyl)imino-1,2,5-trideoxy-D-glucitol-3-yl]-D-lactoyl}-L-alanine benzyl ester

2-acetamido-4,6-O-benzylidene-1,5-(benzyloxycarbonyl)imino-1,2,5-trideoxy-3-O-[(1R)-1-(4-nitrophenoxy)carbonyl]ethyl-D-glucitol

Refernces

• 1、 Kiso, Makoto,Furui, Hiroyasu,Ishida, Hideharu,Hasegawa, Akira. "Studies on selectin binding inhibitors: Synthesis of sialyl-Lewis X and sialyl-Lewis a epitope analogs containing 2-acetamido derivative of N-methyl-1-deoxynojirimycin". . p. 1 - 14. Retrieved 2007/10/03.