N-<<(p-nitrobenzyl)oxy>carbonyl>-O-<<(p-nitrobenzyl)oxy>carbonyl>thienamycin p-nitrobenzyl ester

Base Information

• Chemical Name: N-<<(p-nitrobenzyl)oxy>carbonyl>-O-<<(p-nitrobenzyl)oxy>carbonyl>thienamycin p-nitrobenzyl ester
• CAS No.: 72778-09-7
• Molecular Formula: C₃₄H₃₁N₅O₁₄S
• Molecular Weight: 765.711
• Mol file: 72778-09-7.mol

Synonyms:N-<<(p-nitrobenzyl)oxy>carbonyl>-O-<<(p-nitrobenzyl)oxy>carbonyl>thienamycin p-nitrobenzyl ester

Chemical Property of N-<<(p-nitrobenzyl)oxy>carbonyl>-O-<<(p-nitrobenzyl)oxy>carbonyl>thienamycin p-nitrobenzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-<<(p-nitrobenzyl)oxy>carbonyl>-O-<<(p-nitrobenzyl)oxy>carbonyl>thienamycin p-nitrobenzyl ester

There total 44 articles about N-<<(p-nitrobenzyl)oxy>carbonyl>-O-<<(p-nitrobenzyl)oxy>carbonyl>thienamycin p-nitrobenzyl 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: 58.0%

p-nitrobenzyl (5R,6S)-2-<<2-<<<(p-nitrobenzyl)oxy>carbonyl>amino>ethyl>thio>-6-<(R)-1-hydroxyethyl>carbapen-2-em-3-carboxylate (64067-13-6) + 4-nitrobenzyl chloroformate (4457-32-3) → N-<<(p-nitrobenzyl)oxy>carbonyl>-O-<<(p-nitrobenzyl)oxy>carbonyl>thienamycin p-nitrobenzyl ester (72778-09-7)

Guidance literature:

With dmap; In dichloromethane; for 2.5h; Ambient temperature;

DOI:10.1021/jo01294a044

Reference yield: 51.0%

(3S,4R)-4-([2-(p-nitrobenzyloxycarbonylamino)ethylthio]carbonylmethyl)-3-[(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-1-[1-(p-nitrobenzyloxycarbonyl)-1-triisopropoxyphosphoranylidenemethyl]-2-azetidinone → (+/-)-p-nitrobenzyl 3-<2-(p-nitrobenzyloxycarbonylamino)ethylthio>-6α-<(1R*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (65991-26-6,67576-51-6,72778-09-7,79299-27-7,92217-98-6,106758-28-5)

Guidance literature:

With hydroquinone; In 5,5-dimethyl-1,3-cyclohexadiene; chloroform; ethyl acetate;

Reference yield: 41.5%

2-(4-nitrobenzyloxycarbonylamino)ethanethiol (65750-59-6) + (5R,6S)-3-(Diphenoxy-phosphoryloxy)-6-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (78072-36-3,96093-91-3,96093-95-7) → (+/-)-p-nitrobenzyl 3-<2-(p-nitrobenzyloxycarbonylamino)ethylthio>-6α-<(1R*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (65991-26-6,67576-51-6,72778-09-7,79299-27-7,92217-98-6,106758-28-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at -15 ℃; for 20h;

DOI:10.1039/P19810000964

upstream raw materials:

2-(4-nitrobenzyloxycarbonylamino)ethanethiol

(5R,6S)-3-(Diphenoxy-phosphoryloxy)-6-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(3S,4R)-4-(2,2-dimethoxyethyl)-3-[(1RS)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-2-oxoazetidine

magnesium 4-nitrobenzyl malonate

Refernces

• 1、 Bateson, John H.,Robins, Alison M.,Southgate, Robert. "Olivanic Acid Analogues. Part 8. Halogenation and Sulphenylation Reactions leading Selectively to cis-Carbapenem Precursors; Stereospecific Synthesis of (+/-)-6-Epithienamycin". . p. 29 - 35. Retrieved 2007/10/02.
• 2、 Kametani, Tetsuji,Huang, Shyh-Pyng,Nagahara, Takayasu,Yokohama, Shuichi,Ihara, Masataka. "Studies on the Syntheses of Heterocyclic Compounds. Part 877. An Alternative Synthesis of Protected (+/-)-Thienamycin and a Related Compound". . p. 964 - 968. Retrieved 2007/10/02.