N-{1-[(2R,3R,5S)-3-Benzenesulfinyl-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-acetamide

Base Information

• Chemical Name: N-{1-[(2R,3R,5S)-3-Benzenesulfinyl-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-acetamide
• CAS No.: 132336-23-3
• Molecular Formula: C₃₃H₃₇N₃O₅SSi
• Molecular Weight: 615.825
• Mol file: 132336-23-3.mol

Synonyms:N-{1-[(2R,3R,5S)-3-Benzenesulfinyl-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-acetamide

Chemical Property of N-{1-[(2R,3R,5S)-3-Benzenesulfinyl-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-{1-[(2R,3R,5S)-3-Benzenesulfinyl-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-acetamide

There total 6 articles about N-{1-[(2R,3R,5S)-3-Benzenesulfinyl-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-acetamide 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:

N4-acetyl-1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-β-D-erythro-pentofuranosyl>cytosine (132336-20-0) → N-{1-[(2R,3R,5S)-3-Benzenesulfinyl-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-acetamide (132336-23-3)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1246/cl.1990.1459

Reference yield:

(5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one (102717-29-3) → N-{1-[(2R,3R,5S)-3-Benzenesulfinyl-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-acetamide (132336-23-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) lithium cyclohexylisopropylamide (LCIA) / THF, -20 deg C

2: DIBAL-H / tetrahydrofuran / -78 °C

3: 69 percent / DMAP / CH₂Cl₂

4: 93 percent / SnCl₄ / 1,2-dichloro-ethane / 4 h / 0 °C

5: mCPBA / CH₂Cl₂ / 3 h / 0 °C

With dmap; diisobutylaluminium hydride; lithium cyclohexylisopropylamide; 3-chloro-benzenecarboperoxoic acid; tin(IV) chloride; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1246/cl.1990.1459

Reference yield:

(3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylsulfanyl-tetrahydro-furan-2-ol (142495-48-5) → N-{1-[(2R,3R,5S)-3-Benzenesulfinyl-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-acetamide (132336-23-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 69 percent / DMAP / CH₂Cl₂

2: 93 percent / SnCl₄ / 1,2-dichloro-ethane / 4 h / 0 °C

3: mCPBA / CH₂Cl₂ / 3 h / 0 °C

With dmap; 3-chloro-benzenecarboperoxoic acid; tin(IV) chloride; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1246/cl.1990.1459

upstream raw materials:

N⁴-acetyl-1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-β-D-erythro-pentofuranosyl>cytosine

N⁴-acetyl-O-trimethylsilylcytosine

(3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylsulfanyl-tetrahydro-furan-2-ol

(5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one

Downstream raw materials:

N⁴-acetyl-1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-glycero-pento-2-enofuranosyl>cytosine