(1S,5S,6R)-5-[(Benzyloxycarbonyl-methyl-amino)-methyl]-7-oxa-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(1S,5S,6R)-5-[(Benzyloxycarbonyl-methyl-amino)-methyl]-7-oxa-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid tert-butyl ester
CAS No.:189184-53-0
Molecular Formula:C₂₁H₂₇NO₅
Molecular Weight:373.449
Hs Code.:

Synonyms:(1S,5S,6R)-5-[(Benzyloxycarbonyl-methyl-amino)-methyl]-7-oxa-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid tert-butyl ester

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Chemical Property of (1S,5S,6R)-5-[(Benzyloxycarbonyl-methyl-amino)-methyl]-7-oxa-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid tert-butyl ester

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Technology Process of (1S,5S,6R)-5-[(Benzyloxycarbonyl-methyl-amino)-methyl]-7-oxa-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid tert-butyl ester

There total 4 articles about (1S,5S,6R)-5-[(Benzyloxycarbonyl-methyl-amino)-methyl]-7-oxa-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid tert-butyl 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: 100.0%

: 189184-91-6
(R)-5-[(Benzyloxycarbonyl-methyl-amino)-methyl]-cyclohexa-1,3-dienecarboxylic acid tert-butyl ester

: 189184-53-0
(1S,5S,6R)-5-[(Benzyloxycarbonyl-methyl-amino)-methyl]-7-oxa-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid tert-butyl ester

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 3h; Ambient temperature;
DOI:10.1016/S0040-4020(97)00182-8

Reference yield:

: 79328-85-1
N-benzyloxycarbonyl-1,2-dihydropyridine

: 189184-53-0
(1S,5S,6R)-5-[(Benzyloxycarbonyl-methyl-amino)-methyl]-7-oxa-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 43 percent / propylene oxide, trifluoroacetic anhydride / CH₂Cl₂ / 3 h / -78 °C

3: 1.) LiHMDS / 1.) THF, -40 to 20 deg C, 2 h, 2.) room temperature, 12 h.

4: 100 percent / m-CPBA / CH₂Cl₂ / 3 h / Ambient temperature

With 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; methyloxirane; lithium hexamethyldisilazane; In dichloromethane;
DOI:10.1016/S0040-4020(97)00182-8

Reference yield:

: 189184-89-2
(1R,4R,6R)-2-Aza-bicyclo[2.2.2]oct-7-ene-2,6-dicarboxylic acid 2-benzyl ester 6-tert-butyl ester

: 189184-53-0
(1S,5S,6R)-5-[(Benzyloxycarbonyl-methyl-amino)-methyl]-7-oxa-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) LiHMDS / 1.) THF, -40 to 20 deg C, 2 h, 2.) room temperature, 12 h.

2: 100 percent / m-CPBA / CH₂Cl₂ / 3 h / Ambient temperature

With 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; In dichloromethane;
DOI:10.1016/S0040-4020(97)00182-8