3',5'-bis-O-(tert-butyldimethylsilyl)-5-(3-phenyl-2,2-(1,3-dithio))propyl-2'-deoxyuridine

Base Information

Chemical Name:3',5'-bis-O-(tert-butyldimethylsilyl)-5-(3-phenyl-2,2-(1,3-dithio))propyl-2'-deoxyuridine
CAS No.:291525-18-3
Molecular Formula:C₃₃H₅₄N₂O₅S₂Si₂
Molecular Weight:679.105
Hs Code.:

Synonyms:3',5'-bis-O-(tert-butyldimethylsilyl)-5-(3-phenyl-2,2-(1,3-dithio))propyl-2'-deoxyuridine

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Chemical Property of 3',5'-bis-O-(tert-butyldimethylsilyl)-5-(3-phenyl-2,2-(1,3-dithio))propyl-2'-deoxyuridine

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Technology Process of 3',5'-bis-O-(tert-butyldimethylsilyl)-5-(3-phenyl-2,2-(1,3-dithio))propyl-2'-deoxyuridine

There total 3 articles about 3',5'-bis-O-(tert-butyldimethylsilyl)-5-(3-phenyl-2,2-(1,3-dithio))propyl-2'-deoxyuridine 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: 52.5%

: 31593-52-9
2-benzyl-1,3-dithiane

: 291525-17-2
3′,5′-bis-O-(tert-butyldimethylsilyl)-5-bromomethyl-2'-deoxyuridine

: 291525-18-3
3',5'-bis-O-(tert-butyldimethylsilyl)-5-(3-phenyl-2,2-(1,3-dithio))propyl-2'-deoxyuridine

Guidance literature:: 2-benzyl-1,3-dithiane; With n-butyllithium; In tetrahydrofuran; cyclohexane; at -40 ℃; for 12h;

3′,5′-bis-O-(tert-butyldimethylsilyl)-5-bromomethyl-2'-deoxyuridine; In tetrahydrofuran; cyclohexane; at -78 ℃; for 12h; Further stages.;
DOI:10.1021/jo000271s

Reference yield:

: 122-78-1
phenylacetaldehyde

: 291525-18-3
3',5'-bis-O-(tert-butyldimethylsilyl)-5-(3-phenyl-2,2-(1,3-dithio))propyl-2'-deoxyuridine

Guidance literature:: Multi-step reaction with 2 steps

1.1: 91 percent / BF₃*OEt₂ / 0.75 h / Heating

2.1: n-BuLi / tetrahydrofuran; cyclohexane / 12 h / -40 °C

2.2: 52.5 percent / tetrahydrofuran; cyclohexane / 12 h / -78 °C

With n-butyllithium; boron trifluoride diethyl etherate; In tetrahydrofuran; cyclohexane; 1.1: Cyclization / 2.1: Metallation / 2.2: Substitution;
DOI:10.1021/jo000271s

Reference yield:

: 40733-26-4
3',5'-O-di(tert-butyldimethylsilyl)thymidine

: 291525-18-3
3',5'-bis-O-(tert-butyldimethylsilyl)-5-(3-phenyl-2,2-(1,3-dithio))propyl-2'-deoxyuridine

Guidance literature:: Multi-step reaction with 2 steps

1.1: 46 percent / NBS; benzoyl peroxide / CCl₄ / 1 h / Heating

2.1: n-BuLi / tetrahydrofuran; cyclohexane / 12 h / -40 °C

2.2: 52.5 percent / tetrahydrofuran; cyclohexane / 12 h / -78 °C

With N-Bromosuccinimide; n-butyllithium; dibenzoyl peroxide; In tetrahydrofuran; tetrachloromethane; cyclohexane; 1.1: Bromination / 2.1: Metallation / 2.2: Substitution;
DOI:10.1021/jo000271s