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

Base Information

• Chemical Name: 1-[(2R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-oxo-5-trityloxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione
• CAS No.: 117136-39-7
• Molecular Formula: C₃₄H₃₈N₂O₆Si
• Molecular Weight: 598.771
• Mol file: 117136-39-7.mol

Synonyms:1-[(2R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-oxo-5-trityloxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

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

There total 1 articles about 1-[(2R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-oxo-5-trityloxymethyl-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: 89.0%

trityl chloride (76-83-5) + 1-[(2R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxymethyl-3-oxo-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione → 1-[(2R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-oxo-5-trityloxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione (117136-39-7)

Guidance literature:

With pyridine; silver nitrate; In tetrahydrofuran; Ambient temperature;

DOI:10.1016/0040-4020(96)00684-9

Reference yield:

1-[(2R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-oxo-5-trityloxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione (117136-39-7) → [(1R,2R,4R,5S)-2-(4-Hydroxy-2-oxo-2H-pyrimidin-1-yl)-4-trityloxymethyl-3,6-dioxa-bicyclo[3.1.0]hex-1-yl]-phosphonic acid diethyl ester (181256-77-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) LHMDS / 1.) THF, -78 deg C, 2.) THF, from -78 deg C to 0 deg C, 2 h

2: 81 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.) 0 deg C, 2 h, 2.) RT, 1h

3: 79 percent / triflyl chloride, 4-pyrrolidinopyridine / CH₂Cl₂ / 1 h / Ambient temperature

With trifluoromethane sulfonyl chloride; tetrabutyl ammonium fluoride; 4-pyrrolidin-1-ylpyridine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0040-4020(96)00684-9

Reference yield:

1-[(2R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-oxo-5-trityloxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione (117136-39-7) → [(2R,3R,4R,5R)-3,4-Dihydroxy-2-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-5-trityloxymethyl-tetrahydro-furan-3-yl]-phosphonic acid diethyl ester (181256-76-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) LHMDS / 1.) THF, -78 deg C, 2.) THF, from -78 deg C to 0 deg C, 2 h

2: 81 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.) 0 deg C, 2 h, 2.) RT, 1h

With tetrabutyl ammonium fluoride; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1016/0040-4020(96)00684-9

upstream raw materials:

trityl chloride

Downstream raw materials:

[(2R,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-5-trityloxymethyl-tetrahydro-furan-3-yl]-phosphonic acid diethyl ester

[(1R,2R,4R,5S)-2-(4-Hydroxy-2-oxo-2H-pyrimidin-1-yl)-4-trityloxymethyl-3,6-dioxa-bicyclo[3.1.0]hex-1-yl]-phosphonic acid diethyl ester

[(2R,3R,4R,5R)-3,4-Dihydroxy-2-(4-hydroxy-2-oxo-2H-pyrimidin-1-yl)-5-trityloxymethyl-tetrahydro-furan-3-yl]-phosphonic acid diethyl ester