Carbonic acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (E)-4-(tert-butyl-diphenyl-silanyloxy)-but-2-enyl ester

Base Information

• Chemical Name: Carbonic acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (E)-4-(tert-butyl-diphenyl-silanyloxy)-but-2-enyl ester
• CAS No.: 362513-93-7
• Molecular Formula: C₃₁H₃₇N₅O₇Si
• Molecular Weight: 619.75
• Mol file: 362513-93-7.mol

Synonyms:Carbonic acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (E)-4-(tert-butyl-diphenyl-silanyloxy)-but-2-enyl ester

Chemical Property of Carbonic acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (E)-4-(tert-butyl-diphenyl-silanyloxy)-but-2-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Carbonic acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (E)-4-(tert-butyl-diphenyl-silanyloxy)-but-2-enyl ester

There total 4 articles about Carbonic acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (E)-4-(tert-butyl-diphenyl-silanyloxy)-but-2-enyl 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: 65.0%

3'-azido-2',3'-deoxythymidine (30516-87-1,399024-19-2) + (E)-4-(tert-butyldiphenylsilyloxy)-2-buten-1-ol (92808-78-1) + 1,1'-carbonyldiimidazole (530-62-1) → Carbonic acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (E)-4-(tert-butyl-diphenyl-silanyloxy)-but-2-enyl ester (362513-93-7)

Guidance literature:

3'-azido-2',3'-deoxythymidine; 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

(E)-4-(tert-butyldiphenylsilyloxy)-2-buten-1-ol; In N,N-dimethyl-formamide; at 60 ℃; Further stages.;

DOI:10.1021/jm010863i

Reference yield:

(Z)-4-((tert-butyldiphenylsilyl)oxy)but-2-en-1-ol (87770-83-0) → Carbonic acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (E)-4-(tert-butyl-diphenyl-silanyloxy)-but-2-enyl ester (362513-93-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 83 percent / PCC; Celite / CH₂Cl₂ / 2 h / 25 °C

2.1: 79 percent / DIBAL-H / diethyl ether; hexane / 1.42 h / -78 - 25 °C

3.1: dimethylformamide / 2 h / 20 °C

3.2: 65 percent / dimethylformamide / 60 °C

With Celite; diisobutylaluminium hydride; pyridinium chlorochromate; In diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm010863i

Reference yield:

(E)-4-(t-butyldiphenylsilyl)oxy-2-butenal (131380-48-8) → Carbonic acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (E)-4-(tert-butyl-diphenyl-silanyloxy)-but-2-enyl ester (362513-93-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 79 percent / DIBAL-H / diethyl ether; hexane / 1.42 h / -78 - 25 °C

2.1: dimethylformamide / 2 h / 20 °C

2.2: 65 percent / dimethylformamide / 60 °C

With diisobutylaluminium hydride; In diethyl ether; hexane; N,N-dimethyl-formamide;

DOI:10.1021/jm010863i

upstream raw materials:

3'-azido-2',3'-deoxythymidine

(E)-4-(tert-butyldiphenylsilyloxy)-2-buten-1-ol

1,1'-carbonyldiimidazole

(E)-4-(t-butyldiphenylsilyl)oxy-2-butenal