[(S)-((1S,2S)-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)-((1S,2S)-2-Hydroxymethyl-cyclopropyl)-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-methyl]-carbamic acid benzyl ester
• CAS No.: 420130-97-8
• Molecular Formula: C₁₉H₂₅NO₆
• Molecular Weight: 363.411
• Mol file: 420130-97-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(S)-((1S,2S)-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)-((1S,2S)-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:

diazomethane (186581-53-3,908094-01-9,334-88-3) + N-Cbz-(O-Me)-E-2,3-L-dehydroglutamate OBO ester (335170-37-1) → [(S)-((1R,2R)-2-Hydroxymethyl-cyclopropyl)-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-methyl]-carbamic acid benzyl ester (420130-98-9) + [(S)-((1S,2S)-2-Hydroxymethyl-cyclopropyl)-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-methyl]-carbamic acid benzyl ester (420130-97-8)

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:

1-[N-(benzyloxycarbonyl)-(1S)-1-amino-2-oxoethyl]-4-methyl-2,6,7-trioxa-bicyclo[2.2.2]octane (183671-34-3) → [(S)-((1S,2S)-2-Hydroxymethyl-cyclopropyl)-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-methyl]-carbamic acid benzyl ester (420130-97-8)

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: 85.0%

[(S)-((1S,2S)-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-Azidomethyl-cyclopropyl)-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-methyl]-carbamic acid benzyl ester (561324-07-0)

Guidance literature:

With hydrogen azide; triphenylphosphine; diethylazodicarboxylate; In dichloromethane; benzene; at 0 - 20 ℃;

DOI:10.1016/S0968-0896(02)00554-0

upstream raw materials:

diazomethane

N-Cbz-(O-Me)-E-2,3-L-dehydroglutamate OBO ester

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

Downstream raw materials:

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

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