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

Base Information

Chemical Name:N-(benzyloxycarbonyl)-(2R)-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-(4S)-hydroxy-(5R)-hydroxymethyl-pyrrolidine
CAS No.:325771-72-0
Molecular Formula:C₁₇H₁₉N₃O₆
Molecular Weight:361.354
Hs Code.:

Synonyms:N-(benzyloxycarbonyl)-(2R)-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-(4S)-hydroxy-(5R)-hydroxymethyl-pyrrolidine

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Chemical Property of N-(benzyloxycarbonyl)-(2R)-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-(4S)-hydroxy-(5R)-hydroxymethyl-pyrrolidine

Chemical Property:

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Technology Process of N-(benzyloxycarbonyl)-(2R)-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-(4S)-hydroxy-(5R)-hydroxymethyl-pyrrolidine

There total 9 articles about N-(benzyloxycarbonyl)-(2R)-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-(4S)-hydroxy-(5R)-hydroxymethyl-pyrrolidine 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,3R,5R)-5-(2,4-Dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-3-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

: 325771-72-0
N-(benzyloxycarbonyl)-(2R)-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-(4S)-hydroxy-(5R)-hydroxymethyl-pyrrolidine

Guidance literature:: With sodium tris(acetoxy)borohydride; acetic acid; In acetonitrile; at -15 - 20 ℃; for 0.333333h;
DOI:10.1021/ol007029s

Reference yield:

: (2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

: 325771-72-0
N-(benzyloxycarbonyl)-(2R)-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-(4S)-hydroxy-(5R)-hydroxymethyl-pyrrolidine

Guidance literature:: Multi-step reaction with 7 steps

1: 11.0 g / piperidine / tetrahydrofuran / 12 h / 20 °C

2: N-chlorosuccinimide / hexane / 1 h / 20 °C

3: lithium 2,2,6,6-tetramethylpiperidide / tetrahydrofuran; hexane / -78 - 0 °C

4: 5.92 g / Et₃N / tetrahydrofuran; hexane / 8 h / 20 °C

5: 58 percent / tributylamin; triphenylarsine / palladium(II) acetate / dimethylformamide / 20 h / 65 °C

6: TBAF; acetic acid / tetrahydrofuran / 37 h / -15 - 20 °C

7: 1.44 g / NaB(OAc)3H; acetic acid / acetonitrile / 0.33 h / -15 °C

With piperidine; N-chloro-succinimide; tributyl-amine; triphenyl-arsane; 2,2,6,6-tetramethylpiperidinyl-lithium; tetrabutyl ammonium fluoride; sodium tris(acetoxy)borohydride; acetic acid; triethylamine; palladium diacetate; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; acetonitrile; 5: Heck reaction;
DOI:10.1021/ol007029s

Reference yield:

: 166047-90-1
(2R,3S)-N-[(9-fluorenylmethoxy)carbonyl]-3-hydroxy-2-(hydroxymethyl)pyrrolidine

: 325771-72-0
N-(benzyloxycarbonyl)-(2R)-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-(4S)-hydroxy-(5R)-hydroxymethyl-pyrrolidine

Guidance literature:: Multi-step reaction with 8 steps

1: imidazole / tetrahydrofuran / 2 h / 20 °C

2: 11.0 g / piperidine / tetrahydrofuran / 12 h / 20 °C

3: N-chlorosuccinimide / hexane / 1 h / 20 °C

4: lithium 2,2,6,6-tetramethylpiperidide / tetrahydrofuran; hexane / -78 - 0 °C

5: 5.92 g / Et₃N / tetrahydrofuran; hexane / 8 h / 20 °C

6: 58 percent / tributylamin; triphenylarsine / palladium(II) acetate / dimethylformamide / 20 h / 65 °C

7: TBAF; acetic acid / tetrahydrofuran / 37 h / -15 - 20 °C

8: 1.44 g / NaB(OAc)3H; acetic acid / acetonitrile / 0.33 h / -15 °C

With piperidine; 1H-imidazole; N-chloro-succinimide; tributyl-amine; triphenyl-arsane; 2,2,6,6-tetramethylpiperidinyl-lithium; tetrabutyl ammonium fluoride; sodium tris(acetoxy)borohydride; acetic acid; triethylamine; palladium diacetate; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; acetonitrile; 6: Heck reaction;
DOI:10.1021/ol007029s