1-(2-O-Acetyl-3-C-allyl-3,5-di-O-benzyl-β-D-ribofuranosyl)thymine

Base Information

• Chemical Name: 1-(2-O-Acetyl-3-C-allyl-3,5-di-O-benzyl-β-D-ribofuranosyl)thymine
• CAS No.: 191163-53-8
• Molecular Formula: C₂₉H₃₂N₂O₇
• Molecular Weight: 520.582
• Mol file: 191163-53-8.mol

Synonyms:1-(2-O-Acetyl-3-C-allyl-3,5-di-O-benzyl-β-D-ribofuranosyl)thymine

Chemical Property of 1-(2-O-Acetyl-3-C-allyl-3,5-di-O-benzyl-β-D-ribofuranosyl)thymine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(2-O-Acetyl-3-C-allyl-3,5-di-O-benzyl-β-D-ribofuranosyl)thymine

There total 11 articles about 1-(2-O-Acetyl-3-C-allyl-3,5-di-O-benzyl-β-D-ribofuranosyl)thymine 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: 86.0%

thymin (65-71-4,28806-14-6,691841-57-3) + Acetic acid (2R,3R,4R,5R)-2-acetoxy-4-allyl-4-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-3-yl ester → 1-(2-O-Acetyl-3-C-allyl-3,5-di-O-benzyl-β-D-ribofuranosyl)thymine (191163-53-8)

Guidance literature:

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile;

DOI:10.1039/a608231i

Reference yield: 86.0%

thymin (65-71-4,28806-14-6,691841-57-3) + 3-C-Allyl-1,2-di-O-acetyl-3,5-di-O-benzyl-D-ribofuranose (191163-52-7) → 1-(2-O-Acetyl-3-C-allyl-3,5-di-O-benzyl-β-D-ribofuranosyl)thymine (191163-53-8)

Guidance literature:

With benzenesulfonamide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; 1.) reflux, 1 h, 2.) r.t., 12 h;

Reference yield:

benzyl bromide (100-39-0) → 1-(2-O-Acetyl-3-C-allyl-3,5-di-O-benzyl-β-D-ribofuranosyl)thymine (191163-53-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / NaH / dimethylformamide / 1.) 50 deg C, 1 h, 2.) r.t., 18 h

2: aq. AcOH / 3 h / 90 °C

3: pyridine / 48 h / Ambient temperature

4: 86 percent / BSA, TMS triflate / acetonitrile / 1.) reflux, 1 h, 2.) r.t., 12 h

With pyridine; benzenesulfonamide; trimethylsilyl trifluoromethanesulfonate; sodium hydride; acetic acid; In N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

thymin

3-C-Allyl-1,2-di-O-acetyl-3,5-di-O-benzyl-D-ribofuranose

benzyl bromide

5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose

Downstream raw materials:

1-(3-C-allyl-3,5-di-O-benzyl-β-D-ribo-pentofuranosyl)thymine

(1S,5R,6R,8R)-5-Benzyloxy-6-benzyloxymethyl-8-(thymin-1-yl)-2,7-dioxabicyclo[3.3.0]octane

1-[3,5-Di-O-benzyl-3-C-(2-hydroxyethyl)-β-D-arabinofuranosyl]thymine

1-(3-C-Allyl-3,5-di-O-benzyl-2-O-methylsulfonyl-β-D-ribofuranosyl)thymine