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

Base Information

Chemical Name:(-)-(1S,4S,5S)-N-benzyloxy-4-hydroxy-1-O-(2,2,2-trichloroethyl)-2,3-dideoxyhex-2-enopyranuronamide
CAS No.:398460-13-4
Molecular Formula:C₁₅H₁₆Cl₃NO₅
Molecular Weight:396.655
Hs Code.:

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

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

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

There total 3 articles about (-)-(1S,4S,5S)-N-benzyloxy-4-hydroxy-1-O-(2,2,2-trichloroethyl)-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: 51.0%

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

: 2687-43-6
O-benzylhydoxylamine hydrochloride

: 398460-13-4
(-)-(1S,4S,5S)-N-benzyloxy-4-hydroxy-1-O-(2,2,2-trichloroethyl)-2,3-dideoxyhex-2-enopyranuronamide

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

O-benzylhydoxylamine hydrochloride; With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; for 3h; Further stages.;
DOI:10.1021/ol017026v

Reference yield:

: 57690-62-7
methyl 3,4-di-O-acetyl-1,2-dideoxy-D-arabino-hex-1-enopyranuronate

: 398460-13-4
(-)-(1S,4S,5S)-N-benzyloxy-4-hydroxy-1-O-(2,2,2-trichloroethyl)-2,3-dideoxyhex-2-enopyranuronamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: 69 percent / BF₃*OEt₂ / CH₂Cl₂ / 12 h / -78 °C

2.1: 83 percent / K₂CO₃ / methanol / 4 h / 0 °C

3.1: KOTMS / tetrahydrofuran / 2 h

3.2: 51 percent / EDAC*HCl / dimethylformamide / 3 h

With boron trifluoride diethyl etherate; potassium trimethylsilonate; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane; 1.1: Ferrier reaction;
DOI:10.1021/ol017026v

Reference yield:

: α,β-(4S,5S)-methyl 4-O-acetyl-1-O-(2,2,2-trichloroethyl)-2,3-dideoxyhex-2-enopyranuronate

: 398460-13-4
(-)-(1S,4S,5S)-N-benzyloxy-4-hydroxy-1-O-(2,2,2-trichloroethyl)-2,3-dideoxyhex-2-enopyranuronamide

Guidance literature:: Multi-step reaction with 2 steps

1.1: 83 percent / K₂CO₃ / methanol / 4 h / 0 °C

2.1: KOTMS / tetrahydrofuran / 2 h

2.2: 51 percent / EDAC*HCl / dimethylformamide / 3 h

With potassium trimethylsilonate; potassium carbonate; In tetrahydrofuran; methanol;
DOI:10.1021/ol017026v