(2R,5R)-5-allyl-2-[(1S,2R)-1,3-diacetoxy-2-tert-butoxycarbonylaminopropyl]-pyrrolidine-1,2-dicarboxylic acid, 2-benzyl ester, 1-methyl ester

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Chemical Name:(2R,5R)-5-allyl-2-[(1S,2R)-1,3-diacetoxy-2-tert-butoxycarbonylaminopropyl]-pyrrolidine-1,2-dicarboxylic acid, 2-benzyl ester, 1-methyl ester
CAS No.:372187-27-4
Molecular Formula:C₂₉H₄₀N₂O₁₀
Molecular Weight:576.644
Hs Code.:

Synonyms:(2R,5R)-5-allyl-2-[(1S,2R)-1,3-diacetoxy-2-tert-butoxycarbonylaminopropyl]-pyrrolidine-1,2-dicarboxylic acid, 2-benzyl ester, 1-methyl ester

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Chemical Property of (2R,5R)-5-allyl-2-[(1S,2R)-1,3-diacetoxy-2-tert-butoxycarbonylaminopropyl]-pyrrolidine-1,2-dicarboxylic acid, 2-benzyl ester, 1-methyl ester

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Technology Process of (2R,5R)-5-allyl-2-[(1S,2R)-1,3-diacetoxy-2-tert-butoxycarbonylaminopropyl]-pyrrolidine-1,2-dicarboxylic acid, 2-benzyl ester, 1-methyl ester

There total 13 articles about (2R,5R)-5-allyl-2-[(1S,2R)-1,3-diacetoxy-2-tert-butoxycarbonylaminopropyl]-pyrrolidine-1,2-dicarboxylic acid, 2-benzyl ester, 1-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: 95.0%

: 108-24-7
acetic anhydride

: 372187-50-3
(2R,5R)-5-Allyl-2-((1S,2R)-2-tert-butoxycarbonylamino-1,3-dihydroxy-propyl)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-methyl ester

: 372187-27-4
(2R,5R)-5-allyl-2-[(1S,2R)-1,3-diacetoxy-2-tert-butoxycarbonylaminopropyl]-pyrrolidine-1,2-dicarboxylic acid, 2-benzyl ester, 1-methyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃;
DOI:10.1021/ja016403w

Reference yield:

: 372187-41-2
(2S,5R)-1-methoxycarbonyl-2-benzoxycarbonyl-5-(2-propenyl)-pyrrolidine

: 372187-27-4
(2R,5R)-5-allyl-2-[(1S,2R)-1,3-diacetoxy-2-tert-butoxycarbonylaminopropyl]-pyrrolidine-1,2-dicarboxylic acid, 2-benzyl ester, 1-methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: LiHMDS / tetrahydrofuran / 1 h / -78 °C

1.2: 86 percent / tetrahydrofuran / 1 h / -78 °C

2.1: 85 percent / CSA / methanol / 7 h / 0 °C

3.1: 97 percent / triethylamine; DMAP / CH₂Cl₂ / -50 - 0 °C

4.1: 95 percent / oxalic chloride; DMSO; triethylamine / CH₂Cl₂ / 1 h / -50 - 0 °C

5.1: 90 percent / NaBH₄ / methanol; diethyl ether / -50 - 10 °C

6.1: 98 percent / TBAF; AcOH / tetrahydrofuran / 0 - 20 °C

7.1: 95 percent / triethylamine; DMAP / CH₂Cl₂ / 0 - 20 °C

With dmap; sodium tetrahydroborate; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; acetic acid; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 4.1: Swern oxidation;
DOI:10.1021/ja016403w

Reference yield:

: (2R,5R)-5-Allyl-2-((1R,2R)-2-tert-butoxycarbonylamino-1,3-dihydroxy-propyl)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-methyl ester

: 372187-27-4
(2R,5R)-5-allyl-2-[(1S,2R)-1,3-diacetoxy-2-tert-butoxycarbonylaminopropyl]-pyrrolidine-1,2-dicarboxylic acid, 2-benzyl ester, 1-methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / triethylamine; DMAP / CH₂Cl₂ / -50 - 0 °C

2: 95 percent / oxalic chloride; DMSO; triethylamine / CH₂Cl₂ / 1 h / -50 - 0 °C

3: 90 percent / NaBH₄ / methanol; diethyl ether / -50 - 10 °C

4: 98 percent / TBAF; AcOH / tetrahydrofuran / 0 - 20 °C

5: 95 percent / triethylamine; DMAP / CH₂Cl₂ / 0 - 20 °C

With dmap; sodium tetrahydroborate; oxalyl dichloride; tetrabutyl ammonium fluoride; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 2: Swern oxidation;
DOI:10.1021/ja016403w