ethyl (RS)-2-[(1S,2R,3R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-yl]-2-cyanoacetate

Base Information

• Chemical Name: ethyl (RS)-2-[(1S,2R,3R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-yl]-2-cyanoacetate
• CAS No.: 925672-02-2
• Molecular Formula: C₃₃H₃₃NO₅
• Molecular Weight: 523.629

Synonyms:ethyl (RS)-2-[(1S,2R,3R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-yl]-2-cyanoacetate

Chemical Property of ethyl (RS)-2-[(1S,2R,3R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-yl]-2-cyanoacetate

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of ethyl (RS)-2-[(1S,2R,3R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-yl]-2-cyanoacetate

There total 2 articles about ethyl (RS)-2-[(1S,2R,3R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-yl]-2-cyanoacetate 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: 52.0%

(1S,2R,3R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-yl methanesulfonate (925672-01-1) + ethyl 2-cyanoacetate (105-56-6) → ethyl (RS)-2-[(1S,2R,3R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-yl]-2-cyanoacetate (925672-02-2) + ethyl 2,2-bis[(1S,2R,3R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-yl]-2-cyanoacetate

Guidance literature:

ethyl 2-cyanoacetate; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 1h;

(1S,2R,3R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-yl methanesulfonate; In tetrahydrofuran; at 50 ℃; for 40h;

DOI:10.1016/j.bmc.2006.10.043

Reference yield:

(3aS,4S,6aR)-2,2-dimethyl-6-[(triphenylmethoxy)methyl]-2H,3aH,4H,6aH-cyclopenta[d][1,3]dioxol-4-ol (163226-45-7) → ethyl (RS)-2-[(1S,2R,3R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-yl]-2-cyanoacetate (925672-02-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 93 percent / Et3N / CH2Cl2 / 20 °C / γ-Irradiation

2.1: NaH / tetrahydrofuran / 1 h / 0 °C

2.2: 52 percent / tetrahydrofuran / 40 h / 50 °C

With sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmc.2006.10.043

Reference yield:

ethyl (RS)-2-[(1S,2R,3R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-yl]-2-cyanoacetate (925672-02-2) → 2-(2,2-dimethyl-6-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-3-hydroxy-propionitrile

Guidance literature:

With diisobutylaluminium hydride; In diethyl ether; hexane; at -78 ℃; for 0.5h;

DOI:10.1016/j.bmc.2006.10.043

upstream raw materials:

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

ethyl 2-cyanoacetate

(3aS,4S,6aR)-2,2-dimethyl-6-[(triphenylmethoxy)methyl]-2H,3aH,4H,6aH-cyclopenta[d][1,3]dioxol-4-ol

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