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
Hs Code.:

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

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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

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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%

: 1356848-64-0
2-acetamido-4,6-O-benzylidene-1,5-(benzyloxycarbonyl)imino-1,2,5-trideoxy-3-O-[(1R)-1-(4-nitrophenoxy)carbonyl]ethyl-D-glucitol

: 5557-81-3,5557-83-5,34404-37-0
L-alanine benzyl ester hydrochloride

: 1356848-63-9
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

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

: 1356848-63-9
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

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

: 1356848-63-9
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

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