3'-azido-5'-O-tert-butyldiphenylsilyl-3'-deoxy-2'-O,4'-C-methylene-5-methyluridine

Base Information

• Chemical Name: 3'-azido-5'-O-tert-butyldiphenylsilyl-3'-deoxy-2'-O,4'-C-methylene-5-methyluridine
• CAS No.: 247025-16-7
• Molecular Formula: C₂₇H₃₁N₅O₅Si
• Molecular Weight: 533.659
• Mol file: 247025-16-7.mol

Synonyms:3'-azido-5'-O-tert-butyldiphenylsilyl-3'-deoxy-2'-O,4'-C-methylene-5-methyluridine

Chemical Property of 3'-azido-5'-O-tert-butyldiphenylsilyl-3'-deoxy-2'-O,4'-C-methylene-5-methyluridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3'-azido-5'-O-tert-butyldiphenylsilyl-3'-deoxy-2'-O,4'-C-methylene-5-methyluridine

There total 9 articles about 3'-azido-5'-O-tert-butyldiphenylsilyl-3'-deoxy-2'-O,4'-C-methylene-5-methyluridine 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%

acetic acid 4-azido-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-methanesulfonyloxymethyl-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester → 3'-azido-5'-O-tert-butyldiphenylsilyl-3'-deoxy-2'-O,4'-C-methylene-5-methyluridine (247025-16-7)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃;

DOI:10.1016/S0040-4039(99)01324-6

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 3'-azido-5'-O-tert-butyldiphenylsilyl-3'-deoxy-2'-O,4'-C-methylene-5-methyluridine (247025-16-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 62 percent / Et₃N / CH₂Cl₂ / 20 °C

2: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 20 °C

3: 94 percent / H₂SO₄ / acetic acid / 20 °C

4: 91 percent / SnCl₄ / 1,2-dichloro-ethane / 20 °C

5: 100 percent / K₂CO₃ / methanol / 20 °C

With dmap; sulfuric acid; tin(IV) chloride; potassium carbonate; triethylamine; In methanol; dichloromethane; acetic acid; 1,2-dichloro-ethane; 1: Etherification / 2: Esterification / 3: Acetylation / 4: Substitution / 5: Cyclization;

DOI:10.1016/S0040-4039(99)01324-6

Reference yield:

3-Azido-5-O-benzoyl-4-C-benzoyloxymethyl-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose (153914-98-8) → 3'-azido-5'-O-tert-butyldiphenylsilyl-3'-deoxy-2'-O,4'-C-methylene-5-methyluridine (247025-16-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 86 percent / K₂CO₃ / H₂O; methanol / 0 °C

2: 62 percent / Et₃N / CH₂Cl₂ / 20 °C

3: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 20 °C

4: 94 percent / H₂SO₄ / acetic acid / 20 °C

5: 91 percent / SnCl₄ / 1,2-dichloro-ethane / 20 °C

6: 100 percent / K₂CO₃ / methanol / 20 °C

With dmap; sulfuric acid; tin(IV) chloride; potassium carbonate; triethylamine; In methanol; dichloromethane; water; acetic acid; 1,2-dichloro-ethane; 1: deprotection / 2: Etherification / 3: Esterification / 4: Acetylation / 5: Substitution / 6: Cyclization;

DOI:10.1016/S0040-4039(99)01324-6

upstream raw materials:

tert-butylchlorodiphenylsilane

3-Azido-5-O-benzoyl-4-C-benzoyloxymethyl-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose

3-Azido-3-deoxy-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose

3'-azido-5'-O-tert-butyldiphenylsilyl-3'-deoxy-4'-hydroxymethyl-1',2'-O-isopropylidene-α-D-ribofuranose