(s)-1-[2-deoxy-3,5-O-(1-diethylphosphono-3-p-toluenesulfonyloxypropylidene)-β-D-threo-pentofuranosyl]thymine

Base Information

Chemical Name:(s)-1-[2-deoxy-3,5-O-(1-diethylphosphono-3-p-toluenesulfonyloxypropylidene)-β-D-threo-pentofuranosyl]thymine
CAS No.:214046-57-8
Molecular Formula:C₂₄H₃₃N₂O₁₁PS
Molecular Weight:588.573
Hs Code.:

Synonyms:(s)-1-[2-deoxy-3,5-O-(1-diethylphosphono-3-p-toluenesulfonyloxypropylidene)-β-D-threo-pentofuranosyl]thymine

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Chemical Property of (s)-1-[2-deoxy-3,5-O-(1-diethylphosphono-3-p-toluenesulfonyloxypropylidene)-β-D-threo-pentofuranosyl]thymine

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Technology Process of (s)-1-[2-deoxy-3,5-O-(1-diethylphosphono-3-p-toluenesulfonyloxypropylidene)-β-D-threo-pentofuranosyl]thymine

There total 6 articles about (s)-1-[2-deoxy-3,5-O-(1-diethylphosphono-3-p-toluenesulfonyloxypropylidene)-β-D-threo-pentofuranosyl]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: 90.0%

: 98-59-9
p-toluenesulfonyl chloride

: 183115-62-0
(S)-1-[-2-deoxy-3,5-O-(1-diethylphosphono-3-hydroxypropylidene)-β-D-threo-pentofuranosyl]thymine

: 214046-57-8
(s)-1-[2-deoxy-3,5-O-(1-diethylphosphono-3-p-toluenesulfonyloxypropylidene)-β-D-threo-pentofuranosyl]thymine

Guidance literature:: With pyridine; at 20 ℃; for 72h;
DOI:10.1016/S0040-4020(98)00654-1

Reference yield:

: 214038-73-0
trimethyl 3-benzoyloxyorthopropionate

: 214046-57-8
(s)-1-[2-deoxy-3,5-O-(1-diethylphosphono-3-p-toluenesulfonyloxypropylidene)-β-D-threo-pentofuranosyl]thymine

Guidance literature:: Multi-step reaction with 6 steps

1: 92 percent / 12 M HCl / dimethylformamide; CH₂Cl₂ / 0 °C / pH 15

2: 80 percent / 2M sodium methoxide / methanol / 6 h / 50 °C

3: 72 percent / pyridine / 20 h / 20 °C

4: 91 percent / acetonitrile / -40 - 0 °C

5: 41 percent / 0.5 M TBAF / tetrahydrofuran / 24 h / 20 °C

6: 90 percent / pyridine / 72 h / 20 °C

With pyridine; hydrogenchloride; tetrabutyl ammonium fluoride; sodium methylate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Substitution / 2: Hydrolysis / 3: silylation / 4: Substitution / 5: desilylation / 6: Tosylation;
DOI:10.1016/S0040-4020(98)00654-1

Reference yield:

: 183115-60-8
(S)-1-[3,5-O-(3-tert-butyldiphenylsilyloxy-1-diethylphosphonopropylidene)-2-deoxy-β-D-threo-pentofuranosyl]thymine

: 214046-57-8
(s)-1-[2-deoxy-3,5-O-(1-diethylphosphono-3-p-toluenesulfonyloxypropylidene)-β-D-threo-pentofuranosyl]thymine

Guidance literature:: Multi-step reaction with 2 steps

1: 41 percent / 0.5 M TBAF / tetrahydrofuran / 24 h / 20 °C

2: 90 percent / pyridine / 72 h / 20 °C

With pyridine; tetrabutyl ammonium fluoride; In tetrahydrofuran; 1: desilylation / 2: Tosylation;
DOI:10.1016/S0040-4020(98)00654-1