Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-azido-6-(2-{[1-phenyl-meth-(Z)-ylidene]-amino}-ethoxy)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-azido-6-(2-{[1-phenyl-meth-(Z)-ylidene]-amino}-ethoxy)-tetrahydro-pyran-4-yl ester
• CAS No.: 78632-89-0
• Molecular Formula: C₂₁H₂₆N₄O₈
• Molecular Weight: 462.459
• Mol file: 78632-89-0.mol

Synonyms:Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-azido-6-(2-{[1-phenyl-meth-(Z)-ylidene]-amino}-ethoxy)-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-azido-6-(2-{[1-phenyl-meth-(Z)-ylidene]-amino}-ethoxy)-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-azido-6-(2-{[1-phenyl-meth-(Z)-ylidene]-amino}-ethoxy)-tetrahydro-pyran-4-yl ester

There total 2 articles about Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-azido-6-(2-{[1-phenyl-meth-(Z)-ylidene]-amino}-ethoxy)-tetrahydro-pyran-4-yl 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:

3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl chloride (67817-37-2) + N-1-Benzal-2-hydroxyaminoethan (124948-52-3) → Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-azido-6-(2-{[1-phenyl-meth-(Z)-ylidene]-amino}-ethoxy)-tetrahydro-pyran-4-yl ester (78632-89-0)

Guidance literature:

With silver trifluoromethanesulfonate; silver carbonate; In dichloromethane; toluene;

DOI:10.1016/S0040-4039(01)90328-4

Reference yield:

2-(N-benzylidenamino)ethanol (770-37-6) + 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl chloride (67817-37-2) → Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-azido-6-(2-{[1-phenyl-meth-(Z)-ylidene]-amino}-ethoxy)-tetrahydro-pyran-4-yl ester (78632-89-0)

Guidance literature:

With molecular sieve; silver trifluoromethanesulfonate; silver carbonate; Multistep reaction; 1) CH₂Cl₂, toluene, 2 h; 2) CH₂Cl₂, toluene, 2 d, room temperature;

DOI:10.1016/S0008-6215(00)82583-5

Reference yield:

Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-azido-6-(2-{[1-phenyl-meth-(Z)-ylidene]-amino}-ethoxy)-tetrahydro-pyran-4-yl ester (78632-89-0) → <2-(4-Methoxycarbonylbutancarboxamido)ethyl>-2-acetamido-6-O-benzoyl-2-desoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyd (78633-00-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 2.41 g / 60percent acetic acid / H₂O / 0.25 h / 80 °C

2: dicyclohexylcarbodiimid / dimethylformamide / 5 h / 0 °C

3: 1) zinc; 2) sodium / 1) acetic acid, room temperature, 30 min; 2) methanol, room temperature, 1 h

4: zinc chloride / neat (no solvent) / 24 h

5: 78 percent / BaO, Ba(OH)2.8H₂O / dimethylformamide / 7 h / Ambient temperature

6: 1.) 60percent acetic acid / 1.) water, 30 min, 80 deg C; 2.) pyridine, dichloromethane, 6 h, room temperature

7: 1) Hg(CN)2, HgBr₂ / 1) MeNO₂, benzene, 55-60 deg C; 2) benzene, 8 h at 60 deg C, then 20 h at room temp.

8: 86 percent / 10percent Pd-C / acetone / 3 h / Ambient temperature

9: 1) Hg(CN)2, HgBr₂ / 1) MeNO₂, room temp., 20 min; 2) MeNO₂, room temp, 3 d

10: 83 percent / CH₂Cl₂; pyridine / 7 h / Ambient temperature

With barium dihydroxide; sodium; mercury(II) cyanide; acetic acid; dicyclohexyl-carbodiimide; mercury dibromide; zinc(II) chloride; barium(II) oxide; zinc; palladium on activated charcoal; In pyridine; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0008-6215(00)82583-5

upstream raw materials:

2-(N-benzylidenamino)ethanol

3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl chloride

N-1-Benzal-2-hydroxyaminoethan

Downstream raw materials:

<2-(4-Methoxycarbonylbutancarboxamido)ethyl>-2-acetamido-3-O-benzyl-2-desoxy-α-D-galactopyranosyd

2<(4-Methoxycarbonylbutancarboxamido)ethyl>-2-acetamido-6-O-benzoyl-3-O-benzyl-2-desoxy-α-D-galactopyranosid

<2-(4-Methoxycarbonylbutancarboxamido)ethyl>-2-acetamido-6-O-benzoyl-2-desoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyd

<2-(4-Methoxycarbonylbutancarboxamido)ethyl>-2-acetamido-3-O-benzyl-4,6-O-benzyliden-2-desoxy-α-D-galactopyranosid