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

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Chemical Name:(2S,3R,4R)-4-(4-Azido-2-azidomethyl-phenoxy)-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
CAS No.:886734-09-4
Molecular Formula:C₂₁H₂₇N₇O₇
Molecular Weight:489.488
Hs Code.:

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

There total 11 articles about (2S,3R,4R)-4-(4-Azido-2-azidomethyl-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: 76.0%

: 886734-10-7
(2S,3R,4R)-4-(4-Azido-2-methanesulfonyloxymethyl-phenoxy)-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

: 886734-09-4
(2S,3R,4R)-4-(4-Azido-2-azidomethyl-phenoxy)-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Guidance literature:: With sodium azide; In dimethyl sulfoxide; at 50 ℃;
DOI:10.1016/j.bmcl.2006.01.083

Reference yield:

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

: 886734-09-4
(2S,3R,4R)-4-(4-Azido-2-azidomethyl-phenoxy)-3-methoxycarbonylmethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 7 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

6.1: 99 percent / Et₃N / CH₂Cl₂ / 3 h / 0 °C

7.1: 76 percent / NaN₃ / dimethylsulfoxide / 50 °C

With sodium azide; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; hydrogen; thiamine diphosphate; acetic acid; triethylamine; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; 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

: 886734-09-4
(2S,3R,4R)-4-(4-Azido-2-azidomethyl-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: 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

4.1: 99 percent / Et₃N / CH₂Cl₂ / 3 h / 0 °C

5.1: 76 percent / NaN₃ / dimethylsulfoxide / 50 °C

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