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

Base Information

Chemical Name:cis-5'-O-[4-(R)-(3-chlorophenyl)-2-oxo-1,3,2-dioxaphosphorinan-2-yl]cytosine-1-β-D-arabinofuranoside
CAS No.:693223-04-0
Molecular Formula:C₁₈H₂₁ClN₃O₈P
Molecular Weight:473.807
Hs Code.:

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

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

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

There total 6 articles about cis-5'-O-[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: 65.0%

: 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

: 693223-04-0
cis-5'-O-[4-(R)-(3-chlorophenyl)-2-oxo-1,3,2-dioxaphosphorinan-2-yl]cytosine-1-β-D-arabinofuranoside

Guidance literature:: With tetraethylammonium fluoride; In tetrahydrofuran; at 20 ℃; for 18h;
DOI:10.1021/ja031818y

Reference yield:

: 587-04-2
m-Chlorobenzaldehyde

: 693223-04-0
cis-5'-O-[4-(R)-(3-chlorophenyl)-2-oxo-1,3,2-dioxaphosphorinan-2-yl]cytosine-1-β-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 8 steps

1.1: LDA / tetrahydrofuran; acetonitrile / 0.5 h / -78 °C

1.2: tetrahydrofuran; hexane / -78 - 20 °C

2.1: 24 g / LiAlH₄ / diethyl ether

3.1: 100 percent / trimethylsilyl triflate / tetrahydrofuran / 1 h / 20 °C

4.1: 7.33 g / trimethylsilyltriflate / CH₂Cl₂ / 48 h / -50 °C

5.1: 75.4 percent / aq. HCl / methanol / 20 °C

6.1: TEA / tetrahydrofuran

6.2: 71 percent / TEA; 4-nitrophenol / tetrahydrofuran

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

7.2: 50 percent / tetrahydrofuran / 18 h / 20 °C

8.1: 65 percent / tetraethylammonium fluoride / tetrahydrofuran / 18 h / 20 °C

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

Reference yield:

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

: 693223-04-0
cis-5'-O-[4-(R)-(3-chlorophenyl)-2-oxo-1,3,2-dioxaphosphorinan-2-yl]cytosine-1-β-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 2 steps

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

1.2: 50 percent / tetrahydrofuran / 18 h / 20 °C

2.1: 65 percent / tetraethylammonium fluoride / tetrahydrofuran / 18 h / 20 °C

With tert-butylmagnesium chloride; tetraethylammonium fluoride; In tetrahydrofuran;
DOI:10.1021/ja031818y