1-[(2R,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylselanyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

Base Information

• Chemical Name: 1-[(2R,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylselanyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione
• CAS No.: 117901-56-1
• Molecular Formula: C₂₇H₄₄N₂O₅SeSi₂
• Molecular Weight: 611.788
• Mol file: 117901-56-1.mol

Synonyms:

Chemical Property of 1-[(2R,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylselanyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(2R,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylselanyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

There total 7 articles about 1-[(2R,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylselanyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione 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: 60.0%

(2R,3R,3aS,9aR)-3-((tert-butyldimethylsilyl)oxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,3a-dihydro-2H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6(9aH)-one (55264-11-4) + diphenyl diselenide (1666-13-3) → 1-<3,5-bis-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl>-uracil (82845-98-5) + 1-[(2R,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylselanyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione (117901-56-1)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; ethanol; for 7h; Product distribution; Heating; or Na/THF; or LiAlH₄/THF;

DOI:10.1021/jo00018a038

Reference yield:

2,2'-Anhydrouridine (3736-77-4) → 1-[(2R,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylselanyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione (117901-56-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / imidazole / dimethylformamide / 3 h / Ambient temperature

2: 1) LiAlH₄ / 1) THF, 10 min, room temp., 2) 18 h, room temp.

With 1H-imidazole; lithium aluminium tetrahydride; In N,N-dimethyl-formamide;

DOI:10.1021/jo00018a038

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 1-[(2R,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylselanyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione (117901-56-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / imidazole / dimethylformamide / 3 h / Ambient temperature

2: 1) LiAlH₄ / 1) THF, 10 min, room temp., 2) 18 h, room temp.

With 1H-imidazole; lithium aluminium tetrahydride; In N,N-dimethyl-formamide;

DOI:10.1021/jo00018a038

upstream raw materials:

(2R,3R,3aS,9aR)-3-((tert-butyldimethylsilyl)oxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,3a-dihydro-2H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6(9aH)-one

diphenyl diselenide

Phenylselenyl chloride

3,5-bis-O,O-(tert-butyldimethylsilyl)-1,2-didehydro-1,2-dideoxy-D-ribofuranose