(2S,3R,4R)-4-(4-Azido-2-hydroxymethyl-phenoxy)-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Base Information

Chemical Name:(2S,3R,4R)-4-(4-Azido-2-hydroxymethyl-phenoxy)-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
CAS No.:886734-16-3
Molecular Formula:C₂₁H₂₈N₄O₈
Molecular Weight:464.475
Hs Code.:

Synonyms:(2S,3R,4R)-4-(4-Azido-2-hydroxymethyl-phenoxy)-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

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Chemical Property of (2S,3R,4R)-4-(4-Azido-2-hydroxymethyl-phenoxy)-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

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Technology Process of (2S,3R,4R)-4-(4-Azido-2-hydroxymethyl-phenoxy)-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

There total 9 articles about (2S,3R,4R)-4-(4-Azido-2-hydroxymethyl-phenoxy)-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl 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: 86.0%

: 886734-15-2
(2S,3R,4R)-4-(4-Amino-2-hydroxymethyl-phenoxy)-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

: 886734-16-3
(2S,3R,4R)-4-(4-Azido-2-hydroxymethyl-phenoxy)-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Guidance literature:: (2S,3R,4R)-4-(4-Amino-2-hydroxymethyl-phenoxy)-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester; With acetic acid; sodium nitrite; at 0 ℃; for 0.0833333h;

With sodium azide; for 1h;
DOI:10.1016/j.bmcl.2006.01.083

Reference yield:

: 39224-61-8
2-hydroxy-5-nitrobenzyl alcohol

: 886734-16-3
(2S,3R,4R)-4-(4-Azido-2-hydroxymethyl-phenoxy)-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: Et₃N / dimethylformamide / 20 °C

2.1: 69 percent / TPP; DIAD / tetrahydrofuran / 20 °C

3.1: 90 percent / H₂ / Pd/C / ethanol / 20 °C

4.1: 86 percent / TBAF / tetrahydrofuran / 20 °C

5.1: NaNO₂; aq. HOAc / 0.08 h / 0 °C

5.2: 86 percent / NaN₃ / 1 h

With di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; hydrogen; thiamine diphosphate; acetic acid; triethylamine; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; 2.1: Mitsunobu reaction;
DOI:10.1016/j.bmcl.2006.01.083

Reference yield:

: 886734-13-0
4-[2-(tert-butyl-dimethyl-silanyloxymethyl)-4-nitro-phenoxy]-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

: 886734-16-3
(2S,3R,4R)-4-(4-Azido-2-hydroxymethyl-phenoxy)-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 90 percent / H₂ / Pd/C / ethanol / 20 °C

2.1: 86 percent / TBAF / tetrahydrofuran / 20 °C

3.1: NaNO₂; aq. HOAc / 0.08 h / 0 °C

3.2: 86 percent / NaN₃ / 1 h

With tetrabutyl ammonium fluoride; hydrogen; acetic acid; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; ethanol;
DOI:10.1016/j.bmcl.2006.01.083