1-[(2R,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-(2-iodo-ethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Base Information

• Chemical Name: 1-[(2R,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-(2-iodo-ethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
• CAS No.: 176097-40-8
• Molecular Formula: C₂₇H₃₃IN₂O₄Si
• Molecular Weight: 604.56
• Mol file: 176097-40-8.mol

Synonyms:1-[(2R,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-(2-iodo-ethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Chemical Property of 1-[(2R,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-(2-iodo-ethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(2R,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-(2-iodo-ethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

There total 5 articles about 1-[(2R,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-(2-iodo-ethyl)-tetrahydro-furan-2-yl]-5-methyl-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: 55.0%

2-[(2R,3S,5R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethanesulfonic acid isopropyl ester (176097-41-9) → 1-[(2R,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-(2-iodo-ethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (176097-40-8)

Guidance literature:

With iodine; triphenylphosphine; In benzene; for 2.5h; Heating;

DOI:10.1016/0040-4039(96)00090-1

Reference yield:

3'-O-tert-Butyldiphenylsilyl-5'-iodo-5'-deoxythymidine (156793-45-2) → 1-[(2R,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-(2-iodo-ethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (176097-40-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / HMPT / tetrahydrofuran

2: 55 percent / I₂, PPh₃ / benzene / Heating

With N,N,N,N,N,N-hexamethylphosphoric triamide; iodine; triphenylphosphine; In tetrahydrofuran; benzene;

DOI:10.1021/ja972768y

Reference yield:

thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → 1-[(2R,4S,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-(2-iodo-ethyl)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (176097-40-8)

Guidance literature:

Multi-step reaction with 4 steps

1: I₂, PPh₃, pyridine

2: imidazole / CH₂Cl₂

3: 74 percent / HMPT / tetrahydrofuran

4: 55 percent / I₂, PPh₃ / benzene / Heating

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; iodine; triphenylphosphine; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1021/ja972768y

upstream raw materials:

2-[(2R,3S,5R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethanesulfonic acid isopropyl ester

1-((2R,4S,5S)-4-hydroxy-5-(iodomethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

3'-O-tert-Butyldiphenylsilyl-5'-iodo-5'-deoxythymidine

thymidine

Downstream raw materials:

C₅₃H₆₄N₄O₁₁SSi₂

C₅₅H₆₆N₄O₁₂SSi₂

N⁶-benzoyl-2'-deoxy-3'-de(phosphinicooxy)adenylylmethylenesulfonylmethylene-(3'->5')-2',5'-dideoxythymidine

N⁶-benzoyl-2'-deoxy-3'-de(phosphinicooxy)-5'-O-(4,4'-dimethoxytrityl)adenylylmethylenesulfonylmethylene-(3'->5')-2',5'-dideoxythymidine