1-Pyrrolidinecarboxylic acid, 3-hydroxy-2-(hydroxymethyl)-5-(1,2,3,4-tetrahydro-2,4-dioxo-5-pyrimidin yl)-, phenylmethyl ester, (2R,5R)-

Base Information

• Chemical Name: 1-Pyrrolidinecarboxylic acid, 3-hydroxy-2-(hydroxymethyl)-5-(1,2,3,4-tetrahydro-2,4-dioxo-5-pyrimidin yl)-, phenylmethyl ester, (2R,5R)-
• CAS No.: 646521-59-7
• Molecular Formula: C17H19N3O6
• Molecular Weight: 361.354
• Mol file: 646521-59-7.mol

Synonyms:

Chemical Property of 1-Pyrrolidinecarboxylic acid, 3-hydroxy-2-(hydroxymethyl)-5-(1,2,3,4-tetrahydro-2,4-dioxo-5-pyrimidin yl)-, phenylmethyl ester, (2R,5R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-Pyrrolidinecarboxylic acid, 3-hydroxy-2-(hydroxymethyl)-5-(1,2,3,4-tetrahydro-2,4-dioxo-5-pyrimidin yl)-, phenylmethyl ester, (2R,5R)-

There total 2 articles about 1-Pyrrolidinecarboxylic acid, 3-hydroxy-2-(hydroxymethyl)-5-(1,2,3,4-tetrahydro-2,4-dioxo-5-pyrimidin yl)-, phenylmethyl ester, (2R,5R)- 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:

(2R,5R)-5-(2,4-Dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-2-hydroxymethyl-3-oxo-pyrrolidine-1-carboxylic acid benzyl ester → (2R,5R)-5-(2,4-Dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-3-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester (646521-59-7)

Guidance literature:

With sodium tris(acetoxy)borohydride; acetic acid; In acetonitrile; at -15 - 20 ℃; for 0.333333h;

DOI:10.1081/NCN-120022832

Reference yield:

N-(benzyloxycarbonyl)-(2R)-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-4-(tert-butyldimethylsilyloxy)-(5R)-(tert-butyldimethylsilyloxymethyl)-aza-3-cyclopenten (325771-77-5) → (2R,5R)-5-(2,4-Dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-3-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester (646521-59-7)

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid; tetrabutylammonium fluoride / tetrahydrofuran / 37 h / -15 - 20 °C

2: NaB(OAc)3H; acetic acid / acetonitrile / 0.33 h / -15 - 20 °C

With tetrabutyl ammonium fluoride; sodium tris(acetoxy)borohydride; acetic acid; In tetrahydrofuran; acetonitrile;

DOI:10.1081/NCN-120022832

Reference yield: 77.0%

methyl iodide (74-88-4) + (2R,5R)-5-(2,4-Dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-3-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester (646521-59-7) → (2R,5R)-3-Hydroxy-2-hydroxymethyl-5-(1-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester (646521-60-0)

Guidance literature:

With N,O-bis-(trimethylsilyl)-acetamide; In dichloromethane; at 20 ℃; for 70h;

DOI:10.1081/NCN-120022832

upstream raw materials:

N-(benzyloxycarbonyl)-(2R)-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-4-(tert-butyldimethylsilyloxy)-(5R)-(tert-butyldimethylsilyloxymethyl)-aza-3-cyclopenten

Downstream raw materials:

(2R,5R)-3-Hydroxy-2-hydroxymethyl-5-(1-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester

N-(9-fluorenylmethoxycarbonyl)-(2R)-(2,4-dioxo-1-methyl-1,2,3,4-tetrahydropyrimidin-5-yl)-(4S)-hydroxy-(5R)-(dimethoxytrityl-hydroxymethyl)-pyrrolidine

N-(9-fluorenylmethoxycarbonyl)-(2R)-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-(4S)-hydroxy-(5R)-(dimethoxytrityl-hydroxymethyl)-pyrrolidine