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

Base Information

• Chemical Name: 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
• CAS No.: 1356848-63-9
• Molecular Formula: C₃₆H₄₁N₃O₉
• Molecular Weight: 659.736
• Mol file: 1356848-63-9.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 7 articles about 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 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%

2-acetamido-4,6-O-benzylidene-1,5-(benzyloxycarbonyl)imino-1,2,5-trideoxy-3-O-[(1R)-1-(4-nitrophenoxy)carbonyl]ethyl-D-glucitol (1356848-64-0) + L-alanine benzyl ester hydrochloride (5557-81-3,5557-83-5,34404-37-0) → 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 (1356848-63-9)

Guidance literature:

L-alanine benzyl ester hydrochloride; With triethylamine; In tetrahydrofuran; dichloromethane; for 0.25h; Inert atmosphere;

2-acetamido-4,6-O-benzylidene-1,5-(benzyloxycarbonyl)imino-1,2,5-trideoxy-3-O-[(1R)-1-(4-nitrophenoxy)carbonyl]ethyl-D-glucitol; In tetrahydrofuran; dichloromethane; for 40h; Inert atmosphere;

DOI:10.1021/ml2002746

Reference yield:

C21H32N2O6Si → 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 (1356848-63-9)

Guidance literature:

Multi-step reaction with 6 steps

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

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

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

4.1: sodium hydride / tetrahydrofuran; oil / 0.5 h / 60 °C / Inert atmosphere

4.2: 21 h / 20 - 60 °C

5.1: pyridine; triethylamine / dichloromethane / 23 h / Inert atmosphere

6.1: triethylamine / tetrahydrofuran; dichloromethane / 0.25 h / Inert atmosphere

6.2: 40 h / Inert atmosphere

With pyridine; tetrabutyl ammonium fluoride; dimethyl sulfide borane; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; oil;

DOI:10.1021/ml2002746

Reference yield:

C21H34N2O4Si → 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 (1356848-63-9)

Guidance literature:

Multi-step reaction with 5 steps

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

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

3.1: sodium hydride / tetrahydrofuran; oil / 0.5 h / 60 °C / Inert atmosphere

3.2: 21 h / 20 - 60 °C

4.1: pyridine; triethylamine / dichloromethane / 23 h / Inert atmosphere

5.1: triethylamine / tetrahydrofuran; dichloromethane / 0.25 h / Inert atmosphere

5.2: 40 h / Inert atmosphere

With pyridine; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; oil;

DOI:10.1021/ml2002746

upstream raw materials:

C₂₁H₃₂N₂O₅Si

2-acetamido-4,6-O-benzylidene-1,5-(benzyloxycarbonyl)imino-3-O-tert-butyldimethylsilyl-1,2,5-trideoxy-D-glucitol

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

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