2S,3R,4R,5R-2,3-diacetoxy-5-acetoxymethylbenzyloxycarbonylaminocyclopentanone oxime

Base Information

Chemical Name:2S,3R,4R,5R-2,3-diacetoxy-5-acetoxymethylbenzyloxycarbonylaminocyclopentanone oxime
CAS No.:140183-61-5
Molecular Formula:C₂₀H₂₄N₂O₉
Molecular Weight:436.419
Hs Code.:

Synonyms:2S,3R,4R,5R-2,3-diacetoxy-5-acetoxymethylbenzyloxycarbonylaminocyclopentanone oxime

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Chemical Property of 2S,3R,4R,5R-2,3-diacetoxy-5-acetoxymethylbenzyloxycarbonylaminocyclopentanone oxime

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Technology Process of 2S,3R,4R,5R-2,3-diacetoxy-5-acetoxymethylbenzyloxycarbonylaminocyclopentanone oxime

There total 12 articles about 2S,3R,4R,5R-2,3-diacetoxy-5-acetoxymethylbenzyloxycarbonylaminocyclopentanone oxime 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: 79.0%

: 140183-60-4,140385-17-7,140385-18-8
Acetic acid (1R,2R,3R,5S)-2-acetoxy-3-acetoxymethyl-4-benzyloxyamino-5-benzyloxycarbonylamino-cyclopentyl ester

: 140183-61-5
2S,3R,4R,5R-2,3-diacetoxy-5-acetoxymethylbenzyloxycarbonylaminocyclopentanone oxime

Guidance literature:: With sodium carbonate; 3-chloro-benzenecarboperoxoic acid; In ethyl acetate; for 1h; Ambient temperature;

Reference yield:

: 140183-59-1
2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-5-imidazol-1-ylthiocarbonyloxy-D-glucose O-benzyl oxime

: 140183-61-5
2S,3R,4R,5R-2,3-diacetoxy-5-acetoxymethylbenzyloxycarbonylaminocyclopentanone oxime

Guidance literature:: Multi-step reaction with 2 steps

1: 54 percent / AIBN, Bu₃SnH / benzene / 3.5 h / Heating

2: 79 percent / Na₂CO₃, m-chloroperbenzoic acid / ethyl acetate / 1 h / Ambient temperature

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium carbonate; 3-chloro-benzenecarboperoxoic acid; In ethyl acetate; benzene;

Reference yield:

: 35946-66-8
2-(acetoxymethyl)-5-{[(benzyloxy)carbonyl]amino}tetrahydropyran-3,4,6-triyl triacetate

: 140183-61-5
2S,3R,4R,5R-2,3-diacetoxy-5-acetoxymethylbenzyloxycarbonylaminocyclopentanone oxime

Guidance literature:: Multi-step reaction with 7 steps

1: 88 percent / (NH₄)2CO₃ / methanol; tetrahydrofuran

2: 74 percent / NH₂OH*HCl, pyridine / methanol

3: 58 percent / CH₂Cl₂

4: 88 percent / pyridine / CH₂Cl₂

5: 82 percent / benzene

6: 54 percent / Bu₃SnH, AIBN / benzene / Heating

7: 79 percent / MCPBA, Na₂CO₃ / ethyl acetate

With pyridine; 2,2'-azobis(isobutyronitrile); hydroxylamine hydrochloride; tri-n-butyl-tin hydride; ammonium carbonate; sodium carbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; benzene;
DOI:10.1016/S0040-4039(00)77717-3