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

Base Information

Chemical Name:N-(9-fluorenylmethoxycarbonyl)-(2R)-(2,4-dioxo-1-methyl-1,2,3,4-tetrahydropyrimidin-5-yl)-(4S)-hydroxy-(5R)-(dimethoxytrityl-hydroxymethyl)-pyrrolidine
CAS No.:325771-86-6
Molecular Formula:C₄₆H₄₃N₃O₈
Molecular Weight:765.863
Hs Code.:

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

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

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

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

There total 16 articles about N-(9-fluorenylmethoxycarbonyl)-(2R)-(2,4-dioxo-1-methyl-1,2,3,4-tetrahydropyrimidin-5-yl)-(4S)-hydroxy-(5R)-(dimethoxytrityl-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: 65.0%

: 40615-36-9
4,4'-dimethoxytrityl chloride

: 325771-82-2
N-(9-fluorenylmethoxycarbonyl)-(2R)-(2,4-dioxo-1-methyl-1,2,3,4-tetrahydropyrimidin-5-yl)-(4S)-hydroxy-(5R)-hydroxymethyl-pyrrolidine

: 325771-86-6
N-(9-fluorenylmethoxycarbonyl)-(2R)-(2,4-dioxo-1-methyl-1,2,3,4-tetrahydropyrimidin-5-yl)-(4S)-hydroxy-(5R)-(dimethoxytrityl-hydroxymethyl)-pyrrolidine

Guidance literature:: With pyridine; at 20 ℃; for 2h;
DOI:10.1081/NCN-120022832

Reference yield:

: 325771-77-5
N-(benzyloxycarbonyl)-(2R)-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-4-(tert-butyldimethylsilyloxy)-(5R)-(tert-butyldimethylsilyloxymethyl)-aza-3-cyclopenten

: 325771-86-6
N-(9-fluorenylmethoxycarbonyl)-(2R)-(2,4-dioxo-1-methyl-1,2,3,4-tetrahydropyrimidin-5-yl)-(4S)-hydroxy-(5R)-(dimethoxytrityl-hydroxymethyl)-pyrrolidine

Guidance literature:: Multi-step reaction with 6 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

3: 77 percent / N,O-bis(trimethylsilyl) acetamide / CH₂Cl₂ / 70 h / 20 °C

4: hydrogen / Pd/C / methanol / 20 °C

5: NaHCO₃ / tetrahydrofuran; dioxane / 3 h / 20 °C

6: 65 percent / pyridine / 2 h / 20 °C

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; tetrabutyl ammonium fluoride; hydrogen; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; acetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; acetonitrile;
DOI:10.1081/NCN-120022832

Reference yield:

: 325771-73-1
N-(benzyloxycarbonyl)-(4S)-(tert-butyldimethylsilyloxy)-(5R)-(tert-butyldimethylsilyloxymethyl)-aza-2-cyclopenten

: 325771-86-6
N-(9-fluorenylmethoxycarbonyl)-(2R)-(2,4-dioxo-1-methyl-1,2,3,4-tetrahydropyrimidin-5-yl)-(4S)-hydroxy-(5R)-(dimethoxytrityl-hydroxymethyl)-pyrrolidine

Guidance literature:: Multi-step reaction with 7 steps

1: 58 percent / Pd(OAc)2; AsPh₃; Bu₃N / dimethylformamide / 20 h / 65 °C

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

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

4: 77 percent / N,O-bis(trimethylsilyl) acetamide / CH₂Cl₂ / 70 h / 20 °C

5: hydrogen / Pd/C / methanol / 20 °C

6: NaHCO₃ / tetrahydrofuran; dioxane / 3 h / 20 °C

7: 65 percent / pyridine / 2 h / 20 °C

With pyridine; palladium diacetate; N,O-bis-(trimethylsilyl)-acetamide; tributyl-amine; triphenyl-arsane; tetrabutyl ammonium fluoride; hydrogen; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; acetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Heck coupling;
DOI:10.1081/NCN-120022832