[(S)-((1R,2R)-2-Hydroxymethyl-cyclopropyl)-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-methyl]-carbamic acid benzyl ester

Base Information

Chemical Name:[(S)-((1R,2R)-2-Hydroxymethyl-cyclopropyl)-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-methyl]-carbamic acid benzyl ester
CAS No.:420130-98-9
Molecular Formula:C₁₉H₂₅NO₆
Molecular Weight:363.411
Hs Code.:

Synonyms:[(S)-((1R,2R)-2-Hydroxymethyl-cyclopropyl)-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-methyl]-carbamic acid benzyl ester

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Chemical Property of [(S)-((1R,2R)-2-Hydroxymethyl-cyclopropyl)-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-methyl]-carbamic acid benzyl ester

Chemical Property:

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Technology Process of [(S)-((1R,2R)-2-Hydroxymethyl-cyclopropyl)-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-methyl]-carbamic acid benzyl ester

There total 2 articles about [(S)-((1R,2R)-2-Hydroxymethyl-cyclopropyl)-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-methyl]-carbamic acid 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:

: 186581-53-3,908094-01-9,334-88-3
diazomethane

: 335170-37-1
N-Cbz-(O-Me)-E-2,3-L-dehydroglutamate OBO ester

: 420130-98-9
[(S)-((1R,2R)-2-Hydroxymethyl-cyclopropyl)-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-methyl]-carbamic acid benzyl ester

: 420130-97-8
[(S)-((1S,2S)-2-Hydroxymethyl-cyclopropyl)-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-methyl]-carbamic acid benzyl ester

Guidance literature:: diazomethane; N-Cbz-(O-Me)-E-2,3-L-dehydroglutamate OBO ester; In diethyl ether;

With benzophenone; 1,1'-azobis(1-cyanocyclohexanenitrile); Irradiation;

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 2h; Further stages.;
DOI:10.1021/jo016242e

Reference yield:

: 183671-34-3
1-[N-(benzyloxycarbonyl)-(1S)-1-amino-2-oxoethyl]-4-methyl-2,6,7-trioxa-bicyclo[2.2.2]octane

: 420130-98-9
[(S)-((1R,2R)-2-Hydroxymethyl-cyclopropyl)-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-methyl]-carbamic acid benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 77 percent / CH₂Cl₂ / 0.25 h / 20 °C

2.1: diethyl ether

2.2: AcCN; benzophenone / Irradiation

2.3: DIBAL-H / CH₂Cl₂ / 2 h / -78 °C

In diethyl ether; dichloromethane;
DOI:10.1021/jo016242e

Reference yield: 93.0%

: 420130-98-9
[(S)-((1R,2R)-2-Hydroxymethyl-cyclopropyl)-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-methyl]-carbamic acid benzyl ester

: 561326-82-7
[(S)-((1R,2R)-2-Azidomethyl-cyclopropyl)-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-methyl]-carbamic acid benzyl ester

Guidance literature:: With hydrogen azide; triphenylphosphine; diethylazodicarboxylate; In dichloromethane; benzene; at 0 - 20 ℃;
DOI:10.1016/S0968-0896(02)00554-0