(+)-(2R,5S,6S)-6-O,N-dibenzylhydroxyamino-8-oxo-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octane

Base Information

• Chemical Name: (+)-(2R,5S,6S)-6-O,N-dibenzylhydroxyamino-8-oxo-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octane
• CAS No.: 195525-45-2
• Molecular Formula: C₂₆H₂₆N₂O₃
• Molecular Weight: 414.504
• Mol file: 195525-45-2.mol

Synonyms:(+)-(2R,5S,6S)-6-O,N-dibenzylhydroxyamino-8-oxo-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octane

Chemical Property of (+)-(2R,5S,6S)-6-O,N-dibenzylhydroxyamino-8-oxo-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(2R,5S,6S)-6-O,N-dibenzylhydroxyamino-8-oxo-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octane

There total 2 articles about (+)-(2R,5S,6S)-6-O,N-dibenzylhydroxyamino-8-oxo-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octane 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: 70.0%

(2R,5S,6S,7S/R)-6-O,N-dibenzylhydroxyamino-7-ethoxycarbonyl-8-oxo-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octane → (+)-(2R,5S,6S)-6-O,N-dibenzylhydroxyamino-8-oxo-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octane (195525-45-2)

Guidance literature:

With bis(tri-n-butyltin)oxide; In toluene; for 18h; Heating;

DOI:10.1039/b106782f

Reference yield:

N,O-dibenzylhydroxylamine (4383-24-8) + (2R,5S)-7-ethoxycarbonyl-8-oxo-2-phenyl-1-aza-3-oxa-bicyclo[3.3.0]oct-6-ene (166765-36-2) → (+)-(2R,5S,6S)-6-O,N-dibenzylhydroxyamino-8-oxo-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octane (195525-45-2)

Guidance literature:

With sodium acetate; bis(tri-n-butyltin)oxide; Yield given. Multistep reaction; 1.) MeOH, r.t., 30 min; 2.) toluene;

DOI:10.1016/S0040-4039(97)01312-9

Reference yield: 85.0%

dibenzyl azodicarboxylate (2449-05-0) + (+)-(2R,5S,6S)-6-O,N-dibenzylhydroxyamino-8-oxo-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octane (195525-45-2) → (+)-(2R,5S,6R,7S)-7-[1,2-bis(benzyloxycarbonyl)hydrazino]-6-O,N-dibenzylhydroxyamino-8-oxo-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octane (256451-14-6)

Guidance literature:

(+)-(2R,5S,6S)-6-O,N-dibenzylhydroxyamino-8-oxo-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octane; With lithium diisopropyl amide; at -78 ℃;

dibenzyl azodicarboxylate;

DOI:10.1016/S0957-4166(99)00420-6

upstream raw materials:

N,O-dibenzylhydroxylamine

(2R,5S)-7-ethoxycarbonyl-8-oxo-2-phenyl-1-aza-3-oxa-bicyclo[3.3.0]oct-6-ene

Downstream raw materials:

(+)-(2S,3S)-3-O,N-dibenzylhydroxyl-2-hydroxymethyl-5-oxopyrrolidine

(+)-(2R,5S,6R,7S)-7-[1,2-bis(benzyloxycarbonyl)hydrazino]-6-O,N-dibenzylhydroxyamino-8-oxo-2-phenyl-3-oxa-1-azabicyclo[3.3.0]octane

(3S,4R,5S)-4-O,N-dibenzylhydroxyamino-3-hydrazino-5-hydroxymethyl-2-oxopyrrolidine

(-)-(3S,4R,5S)-3-(1,2-bis[benzyloxycarbonyl]hydrazino)-4-O,N-dibenzylhydroxyamino-3-hydrazino-5-hydroxymethyl-2-oxopyrrolidine