5-[(1S,2R,3R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-yl]isocytosine

Base Information

Chemical Name:5-[(1S,2R,3R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-yl]isocytosine
CAS No.:925672-12-4
Molecular Formula:C₃₂H₃₁N₃O₄
Molecular Weight:521.616
Hs Code.:

Synonyms:5-[(1S,2R,3R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-yl]isocytosine

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Chemical Property of 5-[(1S,2R,3R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-yl]isocytosine

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Technology Process of 5-[(1S,2R,3R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-yl]isocytosine

There total 4 articles about 5-[(1S,2R,3R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-yl]isocytosine 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: 64.0%

: 925672-11-3
ethyl 2-[(1S,2R,3R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-yl]acetate

: 113-00-8
guanidine nitrate

: 109-94-4
formic acid ethyl ester

: 925672-12-4
5-[(1S,2R,3R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-yl]isocytosine

Guidance literature:: ethyl 2-[(1S,2R,3R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-yl]acetate; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

formic acid ethyl ester; In tetrahydrofuran; hexane; at 20 ℃; for 12h;

guanidine nitrate; With sodium ethanolate; In ethanol;
DOI:10.1016/j.bmc.2006.10.043

Reference yield:

: 925672-01-1
(1S,2R,3R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-yl methanesulfonate

: 925672-12-4
5-[(1S,2R,3R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-yl]isocytosine

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / tetrahydrofuran / 1 h / 20 °C

1.2: 72 percent / tetrahydrofuran / 48 h / 38 °C

2.1: 86 percent / LiCl; H₂O / dimethylsulfoxide / 3 h / 175 °C

3.1: lithium diisopropylamide / tetrahydrofuran; hexane / 1 h / -78 °C

3.2: tetrahydrofuran; hexane / 12 h / 20 °C

3.3: 64 percent / EtONa / ethanol

With water; sodium hydride; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; hexane; dimethyl sulfoxide;
DOI:10.1016/j.bmc.2006.10.043

Reference yield:

: 925672-10-2
diethyl 2-[(1S,2R,3R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-yl]malonate

: 925672-12-4
5-[(1S,2R,3R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-yl]isocytosine

Guidance literature:: Multi-step reaction with 2 steps

1.1: 86 percent / LiCl; H₂O / dimethylsulfoxide / 3 h / 175 °C

2.1: lithium diisopropylamide / tetrahydrofuran; hexane / 1 h / -78 °C

2.2: tetrahydrofuran; hexane / 12 h / 20 °C

2.3: 64 percent / EtONa / ethanol

With water; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; hexane; dimethyl sulfoxide;
DOI:10.1016/j.bmc.2006.10.043