3-[(2R,3S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-1-(4-nitro-benzyloxycarbonylmethyl)-4-oxo-azetidin-2-yl]-propionic acid

Base Information

Chemical Name:3-[(2R,3S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-1-(4-nitro-benzyloxycarbonylmethyl)-4-oxo-azetidin-2-yl]-propionic acid
CAS No.:607691-20-3
Molecular Formula:C₂₃H₁₉N₃O₉
Molecular Weight:481.419
Hs Code.:

Synonyms:3-[(2R,3S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-1-(4-nitro-benzyloxycarbonylmethyl)-4-oxo-azetidin-2-yl]-propionic acid

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Chemical Property of 3-[(2R,3S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-1-(4-nitro-benzyloxycarbonylmethyl)-4-oxo-azetidin-2-yl]-propionic acid

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Technology Process of 3-[(2R,3S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-1-(4-nitro-benzyloxycarbonylmethyl)-4-oxo-azetidin-2-yl]-propionic acid

There total 1 articles about 3-[(2R,3S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-1-(4-nitro-benzyloxycarbonylmethyl)-4-oxo-azetidin-2-yl]-propionic acid 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: 95.0%

: 607691-13-4
[(2R,3S)-2-But-3-enyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-azetidin-1-yl]-acetic acid 4-nitro-benzyl ester

: 607691-20-3
3-[(2R,3S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-1-(4-nitro-benzyloxycarbonylmethyl)-4-oxo-azetidin-2-yl]-propionic acid

Guidance literature:: [(2R,3S)-2-But-3-enyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-azetidin-1-yl]-acetic acid 4-nitro-benzyl ester; With ozone;

With sodium chlorite;
DOI:10.1016/S0040-4039(03)01483-7

Reference yield: 93.0%

: 1885-14-9
phenyl chloroformate

: 607691-20-3
3-[(2R,3S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-1-(4-nitro-benzyloxycarbonylmethyl)-4-oxo-azetidin-2-yl]-propionic acid

: 607691-22-5
3-[(2R,3S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-1-(4-nitro-benzyloxycarbonylmethyl)-4-oxo-azetidin-2-yl]-propionic acid phenyl ester

Guidance literature:: With dmap; triethylamine; In tetrahydrofuran;
DOI:10.1016/S0040-4039(03)01483-7

Reference yield:

: 607691-20-3
3-[(2R,3S)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-1-(4-nitro-benzyloxycarbonylmethyl)-4-oxo-azetidin-2-yl]-propionic acid

: 139165-12-1
(6R,7S)-3-Chloro-7-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 93 percent / Et₃N; DMAP / tetrahydrofuran

2: 83 percent / t-BuOLi / -15 - -8 °C

3: 81 percent / (PhO)3P; Cl₂; pyrimidine / CH₂Cl₂

With PYRIMIDINE; triphenyl phosphite; dmap; chlorine; triethylamine; lithium tert-butoxide; In tetrahydrofuran; dichloromethane; 2: Dieckmann cyclization;
DOI:10.1016/S0040-4039(03)01483-7