2-({[(2R,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-carbamoyl}-methyl)-4-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 2-({[(2R,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-carbamoyl}-methyl)-4-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 209852-27-7
• Molecular Formula: C₄₄H₆₆N₄O₈Si₂
• Molecular Weight: 835.201

Synonyms:

Chemical Property of 2-({[(2R,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-carbamoyl}-methyl)-4-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

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Technology Process of 2-({[(2R,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-carbamoyl}-methyl)-4-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 12 articles about 2-({[(2R,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-carbamoyl}-methyl)-4-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl 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: 54.0%

5'-amino-3'-O-(tert-butyldimethylsilyl)-5’-deoxythymidine (130128-70-0) + 4-(tert-Butyl-diphenyl-silanyloxy)-2-carboxymethyl-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester (209852-26-6) → 2-({[(2R,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-carbamoyl}-methyl)-4-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester (209852-27-7)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In acetonitrile;

DOI:10.1016/S0960-894X(98)00189-9

Reference yield:

Pent-4-en-2-ol (111957-98-3,625-31-0) → 2-({[(2R,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-carbamoyl}-methyl)-4-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester (209852-27-7)

Guidance literature:

Multi-step reaction with 12 steps

1: 93 percent / imidazole / dimethylformamide

2: 95 percent / mCPBA / CH₂Cl₂

3: 67 percent / NaN₃, LiOSO₂CF₃ / acetonitrile / Heating

4: 91 percent / imidazole / dimethylformamide

5: 84 percent / aq. AcOH / tetrahydrofuran / Heating

6: 96 percent / PCC, celite / CH₂Cl₂

7: 60 percent / LDA / tetrahydrofuran / -78 °C

8: H₂ / Lindlar's catalyst / ethanol

10: (i-PrO)4Ti

11: H₂ / Pd/C / ethanol

12: 54 percent / DCC, DMAP / acetonitrile

With 1H-imidazole; titanium(IV) isopropylate; dmap; sodium azide; Celite; hydrogen; lithium trifluoromethanesulfonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; pyridinium chlorochromate; lithium diisopropyl amide; palladium on activated charcoal; Lindlar's catalyst; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0960-894X(98)00189-9

Reference yield:

tert-butyldimethyl(pent-4-en-2-yloxy)silane (92775-36-5) → 2-({[(2R,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-carbamoyl}-methyl)-4-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester (209852-27-7)

Guidance literature:

Multi-step reaction with 11 steps

1: 95 percent / mCPBA / CH₂Cl₂

2: 67 percent / NaN₃, LiOSO₂CF₃ / acetonitrile / Heating

3: 91 percent / imidazole / dimethylformamide

4: 84 percent / aq. AcOH / tetrahydrofuran / Heating

5: 96 percent / PCC, celite / CH₂Cl₂

6: 60 percent / LDA / tetrahydrofuran / -78 °C

7: H₂ / Lindlar's catalyst / ethanol

9: (i-PrO)4Ti

10: H₂ / Pd/C / ethanol

11: 54 percent / DCC, DMAP / acetonitrile

With 1H-imidazole; titanium(IV) isopropylate; dmap; sodium azide; Celite; hydrogen; lithium trifluoromethanesulfonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; pyridinium chlorochromate; lithium diisopropyl amide; palladium on activated charcoal; Lindlar's catalyst; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0960-894X(98)00189-9

upstream raw materials:

5'-amino-3'-O-(tert-butyldimethylsilyl)-5’-deoxythymidine

4-(tert-Butyl-diphenyl-silanyloxy)-2-carboxymethyl-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Pent-4-en-2-ol

tert-butyldimethyl(pent-4-en-2-yloxy)silane

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