2'-O-acetyl-3'-C-acetyloxyethyl-3',5'-di-O-benzyl-5-methyl-4'-C-(p-toluenesulfonyloxymethyl)uridine

Base Information

• Chemical Name: 2'-O-acetyl-3'-C-acetyloxyethyl-3',5'-di-O-benzyl-5-methyl-4'-C-(p-toluenesulfonyloxymethyl)uridine
• CAS No.: 457068-04-1
• Molecular Formula: C₃₈H₄₂N₂O₁₂S
• Molecular Weight: 750.824
• Mol file: 457068-04-1.mol

Synonyms:2'-O-acetyl-3'-C-acetyloxyethyl-3',5'-di-O-benzyl-5-methyl-4'-C-(p-toluenesulfonyloxymethyl)uridine

Chemical Property of 2'-O-acetyl-3'-C-acetyloxyethyl-3',5'-di-O-benzyl-5-methyl-4'-C-(p-toluenesulfonyloxymethyl)uridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2'-O-acetyl-3'-C-acetyloxyethyl-3',5'-di-O-benzyl-5-methyl-4'-C-(p-toluenesulfonyloxymethyl)uridine

There total 15 articles about 2'-O-acetyl-3'-C-acetyloxyethyl-3',5'-di-O-benzyl-5-methyl-4'-C-(p-toluenesulfonyloxymethyl)uridine 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: 95.0%

thymin (65-71-4,28806-14-6,691841-57-3) + 1,2-di-O-acetyl-3-C-acetoxyethyl-3,5-di-O-benzyl-4-C-(p-toluenesulfonyloxymethyl)-D-ribofuranose (457068-03-0) → 2'-O-acetyl-3'-C-acetyloxyethyl-3',5'-di-O-benzyl-5-methyl-4'-C-(p-toluenesulfonyloxymethyl)uridine (457068-04-1)

Guidance literature:

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; for 9h; Heating;

DOI:10.1021/jo051187l

Reference yield: 87.0%

2,4-dihydroxy-5-methylpyrimidine (65-71-4,80289-22-1) + 1,2-di-O-acetyl-3-C-acetoxyethyl-3,5-di-O-benzyl-4-C-(p-toluenesulfonyloxymethyl)-D-ribofuranose (457068-03-0) → 2'-O-acetyl-3'-C-acetyloxyethyl-3',5'-di-O-benzyl-5-methyl-4'-C-(p-toluenesulfonyloxymethyl)uridine (457068-04-1)

Guidance literature:

With benzenesulfonamide; trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; Heating;

DOI:10.1016/S0040-4039(02)00784-0

Reference yield:

3-C-allyl-3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (197702-06-0) → 2'-O-acetyl-3'-C-acetyloxyethyl-3',5'-di-O-benzyl-5-methyl-4'-C-(p-toluenesulfonyloxymethyl)uridine (457068-04-1)

Guidance literature:

Multi-step reaction with 9 steps

1: aqueous acetic acid / 3 h / 40 °C

2: sodium periodate / tetrahydrofuran; H₂O / 0.75 h / 0 °C

3: 2.9 g / sodium hydroxide / tetrahydrofuran; H₂O / 18 h / 20 °C

4: 65 percent / sodium hydride / dimethylformamide / 1.5 h / 20 °C

5: 93 percent / Et₃N; DMAP / CH₂Cl₂ / 19 h / 20 °C

6: NaIO₄; H₂O / OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / 20 °C

7: 754 mg / sodium tetrahydroborate / tetrahydrofuran; H₂O / 1 h / 0 °C

8: 98 percent / H₂SO₄; acetic acid / 6 h / 20 °C

9: 95 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / 1,2-dichloro-ethane / 9 h / Heating

With dmap; sodium hydroxide; sodium tetrahydroborate; sodium periodate; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; water; sodium hydride; acetic acid; triethylamine; osmium(VIII) oxide; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; tert-butyl alcohol; 3: aldol-Cannizzaro reaction;

DOI:10.1021/jo051187l

upstream raw materials:

2,4-dihydroxy-5-methylpyrimidine

1,2-di-O-acetyl-3-C-acetoxyethyl-3,5-di-O-benzyl-4-C-(p-toluenesulfonyloxymethyl)-D-ribofuranose

thymin

3-O-benzyl-4-C-(hydroxymethyl)-1,2-di-O-isopropylidene-3-C-vinyl-α-D-ribofuranose

Downstream raw materials:

1-(3a-benzyloxy-7a-benzyloxymethyl-3-oxo-hexahydro-furo[2,3-c]pyran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

1-((2R,3S,3aS,7aR)-3a-Benzyloxy-7a-benzyloxymethyl-3-hydroxy-hexahydro-furo[2,3-c]pyran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

1-((2R,3S,3aS,7aR)-3a-Benzyloxy-7a-benzyloxymethyl-3-hydroxy-hexahydro-furo[2,3-c]pyran-2-yl)-3-benzyloxymethyl-5-methyl-1H-pyrimidine-2,4-dione

1-((2R,3S,3aS,7aR)-3a-Benzyloxy-7a-benzyloxymethyl-3-methoxy-hexahydro-furo[2,3-c]pyran-2-yl)-3-benzyloxymethyl-5-methyl-1H-pyrimidine-2,4-dione