(-)-(1S,4S,5S)-1-O-benzyl-N-benzyloxy-4-hydroxy-2,3-dideoxyhex-2-enopyranuronamide

Base Information

• Chemical Name: (-)-(1S,4S,5S)-1-O-benzyl-N-benzyloxy-4-hydroxy-2,3-dideoxyhex-2-enopyranuronamide
• CAS No.: 398460-17-8
• Molecular Formula: C₂₀H₂₁NO₅
• Molecular Weight: 355.39
• Mol file: 398460-17-8.mol

Synonyms:(-)-(1S,4S,5S)-1-O-benzyl-N-benzyloxy-4-hydroxy-2,3-dideoxyhex-2-enopyranuronamide

Chemical Property of (-)-(1S,4S,5S)-1-O-benzyl-N-benzyloxy-4-hydroxy-2,3-dideoxyhex-2-enopyranuronamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(1S,4S,5S)-1-O-benzyl-N-benzyloxy-4-hydroxy-2,3-dideoxyhex-2-enopyranuronamide

There total 4 articles about (-)-(1S,4S,5S)-1-O-benzyl-N-benzyloxy-4-hydroxy-2,3-dideoxyhex-2-enopyranuronamide 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: 75.0%

O-benzylhydoxylamine hydrochloride (2687-43-6) + (+)-(1S,4S,5S)-methyl 1-O-benzyl-4-hydroxy-2,3-dideoxyhex-2-enopyranuronate (398460-20-3) → (-)-(1S,4S,5S)-1-O-benzyl-N-benzyloxy-4-hydroxy-2,3-dideoxyhex-2-enopyranuronamide (398460-17-8)

Guidance literature:

(+)-(1S,4S,5S)-methyl 1-O-benzyl-4-hydroxy-2,3-dideoxyhex-2-enopyranuronate; With potassium trimethylsilonate; In tetrahydrofuran; for 0.666667h;

O-benzylhydoxylamine hydrochloride; With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; for 14h; Further stages.;

DOI:10.1021/ol017026v

Reference yield:

methyl 3,4-di-O-acetyl-1,2-dideoxy-D-arabino-hex-1-enopyranuronate (57690-62-7) → (-)-(1S,4S,5S)-1-O-benzyl-N-benzyloxy-4-hydroxy-2,3-dideoxyhex-2-enopyranuronamide (398460-17-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 53 percent / BF₃*OEt₂ / CH₂Cl₂ / 96 h / -10 °C

2.1: 96 percent / K₂CO₃ / methanol / 3.5 h

3.1: KOTMS / tetrahydrofuran / 0.67 h

3.2: 75 percent / EDAC*HCl / dimethylformamide / 14 h

With boron trifluoride diethyl etherate; potassium trimethylsilonate; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane; 1.1: Ferrier reaction;

DOI:10.1021/ol017026v

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → (-)-(1S,4S,5S)-1-O-benzyl-N-benzyloxy-4-hydroxy-2,3-dideoxyhex-2-enopyranuronamide (398460-17-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 53 percent / BF₃*OEt₂ / CH₂Cl₂ / 96 h / -10 °C

2.1: 96 percent / K₂CO₃ / methanol / 3.5 h

3.1: KOTMS / tetrahydrofuran / 0.67 h

3.2: 75 percent / EDAC*HCl / dimethylformamide / 14 h

With boron trifluoride diethyl etherate; potassium trimethylsilonate; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane; 1.1: Ferrier reaction;

DOI:10.1021/ol017026v

upstream raw materials:

O-benzylhydoxylamine hydrochloride

(+)-(1S,4S,5S)-methyl 1-O-benzyl-4-hydroxy-2,3-dideoxyhex-2-enopyranuronate

methyl 3,4-di-O-acetyl-1,2-dideoxy-D-arabino-hex-1-enopyranuronate

benzyl alcohol

Downstream raw materials:

(-)-(1S,3S,6R)-3,7-bisbenzyloxy-2-oxa-8-oxo-7-azabicyclo[4.2.0]oct-4-ene