2',3'-di-O-tert-butyldimethylsilyl-5'-O-cis-[4-(R)-(3-chlorophenyl)-2-oxo-1,3,2-dioxaphosphorinan-2-yl]cytosine-1-β-D-arabinofuranoside

Base Information

Chemical Name:2',3'-di-O-tert-butyldimethylsilyl-5'-O-cis-[4-(R)-(3-chlorophenyl)-2-oxo-1,3,2-dioxaphosphorinan-2-yl]cytosine-1-β-D-arabinofuranoside
CAS No.:804561-63-5
Molecular Formula:C₃₀H₄₉ClN₃O₈PSi₂
Molecular Weight:702.332
Hs Code.:

Synonyms:2',3'-di-O-tert-butyldimethylsilyl-5'-O-cis-[4-(R)-(3-chlorophenyl)-2-oxo-1,3,2-dioxaphosphorinan-2-yl]cytosine-1-β-D-arabinofuranoside

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Chemical Property of 2',3'-di-O-tert-butyldimethylsilyl-5'-O-cis-[4-(R)-(3-chlorophenyl)-2-oxo-1,3,2-dioxaphosphorinan-2-yl]cytosine-1-β-D-arabinofuranoside

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Technology Process of 2',3'-di-O-tert-butyldimethylsilyl-5'-O-cis-[4-(R)-(3-chlorophenyl)-2-oxo-1,3,2-dioxaphosphorinan-2-yl]cytosine-1-β-D-arabinofuranoside

There total 8 articles about 2',3'-di-O-tert-butyldimethylsilyl-5'-O-cis-[4-(R)-(3-chlorophenyl)-2-oxo-1,3,2-dioxaphosphorinan-2-yl]cytosine-1-β-D-arabinofuranoside 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: 50.0%

: 87418-91-5
1-[2',3'-di-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl]cytosine

: 805235-83-0
(4R)-(+)-trans-2-(4-nitrophenoxy)-2-oxo-4-(3-chlorophenyl)-1,3,2-dioxaphosphorinane

: 804561-63-5
2',3'-di-O-tert-butyldimethylsilyl-5'-O-cis-[4-(R)-(3-chlorophenyl)-2-oxo-1,3,2-dioxaphosphorinan-2-yl]cytosine-1-β-D-arabinofuranoside

Guidance literature:: 1-[2',3'-di-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl]cytosine; With tert-butylmagnesium chloride; In tetrahydrofuran; at 20 ℃; for 0.5h;

(4R)-(+)-trans-2-(4-nitrophenoxy)-2-oxo-4-(3-chlorophenyl)-1,3,2-dioxaphosphorinane; In tetrahydrofuran; at 20 ℃; for 18h;
DOI:10.1021/ja031818y

Reference yield:

: 51699-45-7
(S)-(-)-1-(3'-Chlorophenyl)-1,3-Propanediol

: 804561-63-5
2',3'-di-O-tert-butyldimethylsilyl-5'-O-cis-[4-(R)-(3-chlorophenyl)-2-oxo-1,3,2-dioxaphosphorinan-2-yl]cytosine-1-β-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 100 percent / trimethylsilyl triflate / tetrahydrofuran / 1 h / 20 °C

2.1: 7.33 g / trimethylsilyltriflate / CH₂Cl₂ / 48 h / -50 °C

3.1: 75.4 percent / aq. HCl / methanol / 20 °C

4.1: TEA / tetrahydrofuran

4.2: 71 percent / TEA; 4-nitrophenol / tetrahydrofuran

5.1: tert-BuMgCl / tetrahydrofuran / 0.5 h / 20 °C

5.2: 50 percent / tetrahydrofuran / 18 h / 20 °C

With hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; TEA; tert-butylmagnesium chloride; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ja031818y

Reference yield:

: 51699-40-2,138307-15-0
3-(3-chlorophenyl)-3-hydroxypropionic acid ethyl ester

: 804561-63-5
2',3'-di-O-tert-butyldimethylsilyl-5'-O-cis-[4-(R)-(3-chlorophenyl)-2-oxo-1,3,2-dioxaphosphorinan-2-yl]cytosine-1-β-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: 24 g / LiAlH₄ / diethyl ether

2.1: 100 percent / trimethylsilyl triflate / tetrahydrofuran / 1 h / 20 °C

3.1: 7.33 g / trimethylsilyltriflate / CH₂Cl₂ / 48 h / -50 °C

4.1: 75.4 percent / aq. HCl / methanol / 20 °C

5.1: TEA / tetrahydrofuran

5.2: 71 percent / TEA; 4-nitrophenol / tetrahydrofuran

6.1: tert-BuMgCl / tetrahydrofuran / 0.5 h / 20 °C

6.2: 50 percent / tetrahydrofuran / 18 h / 20 °C

With hydrogenchloride; lithium aluminium tetrahydride; trimethylsilyl trifluoromethanesulfonate; TEA; tert-butylmagnesium chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1021/ja031818y