(2S,3R,4R)-N-benzyloxycarbonyl-3-hydroxy-4-azidoproline benzyl ester

Base Information

Chemical Name:(2S,3R,4R)-N-benzyloxycarbonyl-3-hydroxy-4-azidoproline benzyl ester
CAS No.:202473-17-4
Molecular Formula:C₂₀H₂₀N₄O₅
Molecular Weight:396.403
Hs Code.:

Synonyms:(2S,3R,4R)-N-benzyloxycarbonyl-3-hydroxy-4-azidoproline benzyl ester

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Chemical Property of (2S,3R,4R)-N-benzyloxycarbonyl-3-hydroxy-4-azidoproline benzyl ester

Chemical Property:

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Technology Process of (2S,3R,4R)-N-benzyloxycarbonyl-3-hydroxy-4-azidoproline benzyl ester

There total 7 articles about (2S,3R,4R)-N-benzyloxycarbonyl-3-hydroxy-4-azidoproline 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: 28.0%

: 159551-90-3
(1R,2S,5S)-6-oxa-3-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid dibenzyl ester

: 202473-17-4
(2S,3R,4R)-N-benzyloxycarbonyl-3-hydroxy-4-azidoproline benzyl ester

Guidance literature:: With sodium azide; ammonium chloride; In water; acetone; at 70 ℃; for 36h;
DOI:10.1016/S0040-4020(97)10352-0

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 202473-17-4
(2S,3R,4R)-N-benzyloxycarbonyl-3-hydroxy-4-azidoproline benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 86 percent / aq. NaOH / tetrahydrofuran / ice/water cooling -> room temperature

2: 71 percent / potassium carbonate; sodium iodide / dimethylformamide

3: 94 percent / N-methylimidazole / tetrahydrofuran / 0 - 30 °C

4: 74 percent / NaBH₄ / 2-methyl-propan-2-ol / 2.5 h / Heating

5: 77 percent / pyridine; H₂O₂ / CH₂Cl₂ / 1.5 h / 0 - 20 °C

6: 54 percent / m-CPBA; 4,4'-thio-(6-tert-butyl-3-methylphenol) / 1,2-dichloro-ethane / Heating

7: 28 percent / NH₄Cl; sodium azide / acetone; H₂O / 36 h / 70 °C

With pyridine; 1-methyl-1H-imidazole; sodium hydroxide; sodium tetrahydroborate; sodium azide; 2,2'-Dimethyl-5,5'-di-tert-butyl-4,4'-dihydroxy-diphenyl-sulfid, Lanotox; dihydrogen peroxide; potassium carbonate; ammonium chloride; 3-chloro-benzenecarboperoxoic acid; sodium iodide; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 1: Acylation / 2: Esterification / 3: Tosylation / 4: Substitution / 5: Elimination / 6: Epoxidation / 7: Ring cleavage;
DOI:10.1016/S0040-4020(97)10352-0

Reference yield:

: 159551-89-0
(S)-2,5-dihydro-pyrrole-1,2-dicarboxylic acid dibenzyl ester

: 202473-17-4
(2S,3R,4R)-N-benzyloxycarbonyl-3-hydroxy-4-azidoproline benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 54 percent / m-CPBA; 4,4'-thio-(6-tert-butyl-3-methylphenol) / 1,2-dichloro-ethane / Heating

2: 28 percent / NH₄Cl; sodium azide / acetone; H₂O / 36 h / 70 °C

With sodium azide; 2,2'-Dimethyl-5,5'-di-tert-butyl-4,4'-dihydroxy-diphenyl-sulfid, Lanotox; ammonium chloride; 3-chloro-benzenecarboperoxoic acid; In water; 1,2-dichloro-ethane; acetone; 1: Epoxidation / 2: Ring cleavage;
DOI:10.1016/S0040-4020(97)10352-0