N⁴-benzoyl-5'-O-tert-butyldiphenylsilyl-3'-O,4'-C-methylenecytidine

Base Information

• Chemical Name: N⁴-benzoyl-5'-O-tert-butyldiphenylsilyl-3'-O,4'-C-methylenecytidine
• CAS No.: 260269-38-3
• Molecular Formula: C₃₃H₃₅N₃O₆Si
• Molecular Weight: 597.743
• Mol file: 260269-38-3.mol

Synonyms:N⁴-benzoyl-5'-O-tert-butyldiphenylsilyl-3'-O,4'-C-methylenecytidine

Chemical Property of N⁴-benzoyl-5'-O-tert-butyldiphenylsilyl-3'-O,4'-C-methylenecytidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁴-benzoyl-5'-O-tert-butyldiphenylsilyl-3'-O,4'-C-methylenecytidine

There total 10 articles about N⁴-benzoyl-5'-O-tert-butyldiphenylsilyl-3'-O,4'-C-methylenecytidine 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: 100.0%

N4-benzoyl-5'-O-tert-butyldiphenylsilyl-4'-C-(p-toluenesulfonyl)oxymethylcytidine (446862-78-8) → N4-benzoyl-5'-O-tert-butyldiphenylsilyl-3'-O,4'-C-methylenecytidine (260269-38-3)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1039/a907218g

Reference yield:

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → N4-benzoyl-5'-O-tert-butyldiphenylsilyl-3'-O,4'-C-methylenecytidine (260269-38-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 67 percent / CH₂Cl₂ / 11 h / 20 °C

2.1: 97 percent / 4,4-dimethylaminopyridine / CH₂Cl₂ / 16 h / 20 °C

3.1: conc. H₂SO₄ / acetic acid / 2 h / 20 °C

3.2: H₂ / 10 percent Pd/C / ethyl acetate; CHCl₃ / 16 h / 20 °C

3.3: pyridine / 49 h / 20 °C

4.1: 82 percent / trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 5 h / Heating

5.1: 73 percent / K₂CO₃ / methanol / 0.25 h / 20 °C

6.1: 100 percent / sodium bis(trimethylsilylamide) / tetrahydrofuran / 1 h / 20 °C

With dmap; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; sodium hexamethyldisilazane; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane; acetic acid; 1,2-dichloro-ethane;

DOI:10.1016/S0040-4020(02)00227-2

Reference yield:

{3-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]-(1S,3R,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)bicyclo[3.3.0]oct-3-yl}methan-1-ol (212970-72-4) → N4-benzoyl-5'-O-tert-butyldiphenylsilyl-3'-O,4'-C-methylenecytidine (260269-38-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 97 percent / 4,4-dimethylaminopyridine / CH₂Cl₂ / 16 h / 20 °C

2.1: conc. H₂SO₄ / acetic acid / 2 h / 20 °C

2.2: H₂ / 10 percent Pd/C / ethyl acetate; CHCl₃ / 16 h / 20 °C

2.3: pyridine / 49 h / 20 °C

3.1: 82 percent / trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 5 h / Heating

4.1: 73 percent / K₂CO₃ / methanol / 0.25 h / 20 °C

5.1: 100 percent / sodium bis(trimethylsilylamide) / tetrahydrofuran / 1 h / 20 °C

With dmap; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; sodium hexamethyldisilazane; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane; acetic acid; 1,2-dichloro-ethane;

DOI:10.1016/S0040-4020(02)00227-2

upstream raw materials:

N⁴-benzoyl-5'-O-tert-butyldiphenylsilyl-4'-C-(p-toluenesulfonyl)oxymethylcytidine

tert-butylchlorodiphenylsilane

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

{3-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]-(1S,3R,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)bicyclo[3.3.0]oct-3-yl}methan-1-ol