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

Base Information

Chemical Name:(1R,2S,5S)-6-oxa-3-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid dibenzyl ester
CAS No.:159551-90-3
Molecular Formula:C₂₀H₁₉NO₅
Molecular Weight:353.375
Hs Code.:

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

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Chemical Property of (1R,2S,5S)-6-oxa-3-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid dibenzyl ester

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Technology Process of (1R,2S,5S)-6-oxa-3-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid dibenzyl ester

There total 19 articles about (1R,2S,5S)-6-oxa-3-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid dibenzyl 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: 54.0%

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

: 159651-34-0
(1S,2S,5R)-6-oxa-3-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid dibenzyl ester

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

Guidance literature:: With 3-methyl-4-hydroxy-5-tert-butylbenzenethiol; 3-chloro-benzenecarboperoxoic acid; In 1,2-dichloro-ethane; Heating;
DOI:10.1016/S0040-4039(00)60753-0

Reference yield: 22.0%

: 40635-67-4
acetoxyisobutyryl bromide

: 202473-13-0
(2S,3RS,4SR)-N-benzyloxycarbonyl-3,4-dihydroxyproline benzyl ester

: benzyl-N-benzyloxycarbonylpyrrole-2-carboxylate

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

Guidance literature:: acetoxyisobutyryl bromide; (2S,3RS,4SR)-N-benzyloxycarbonyl-3,4-dihydroxyproline benzyl ester; In acetonitrile; at 20 ℃; for 1h;

With potassium carbonate; In benzyl alcohol; at 50 ℃; for 24h;
DOI:10.1016/S0040-4020(97)10352-0

Reference yield:

: 159551-87-8
(2S,4R)-N^α-Cbz-4-[(p-toluenesulfonyl)oxy]proline benzyl ester

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

Guidance literature:: Multi-step reaction with 3 steps

1: 74 percent / NaBH₄ / 2-methyl-propan-2-ol / 2.5 h / Heating

2: 77 percent / pyridine; H₂O₂ / CH₂Cl₂ / 1.5 h / 0 - 20 °C

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

With pyridine; sodium tetrahydroborate; 2,2'-Dimethyl-5,5'-di-tert-butyl-4,4'-dihydroxy-diphenyl-sulfid, Lanotox; dihydrogen peroxide; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; 1,2-dichloro-ethane; tert-butyl alcohol; 1: Substitution / 2: Elimination / 3: Epoxidation;
DOI:10.1016/S0040-4020(97)10352-0