2,2-dimethylpropionic acid 2-[(2R,3R,4S)-4-(tert-butyldiphenylsilanyloxy)-2,3-(O-isopropylidenedioxy)cyclopent-1⁽⁵⁾enyl]ethyl ester

Base Information

• Chemical Name: 2,2-dimethylpropionic acid 2-[(2R,3R,4S)-4-(tert-butyldiphenylsilanyloxy)-2,3-(O-isopropylidenedioxy)cyclopent-1⁽⁵⁾enyl]ethyl ester
• CAS No.: 1373313-91-7
• Molecular Formula: C₃₁H₄₂O₅Si
• Molecular Weight: 522.757

Synonyms:2,2-dimethylpropionic acid 2-[(2R,3R,4S)-4-(tert-butyldiphenylsilanyloxy)-2,3-(O-isopropylidenedioxy)cyclopent-1⁽⁵⁾enyl]ethyl ester

Chemical Property of 2,2-dimethylpropionic acid 2-[(2R,3R,4S)-4-(tert-butyldiphenylsilanyloxy)-2,3-(O-isopropylidenedioxy)cyclopent-1⁽⁵⁾enyl]ethyl ester

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Technology Process of 2,2-dimethylpropionic acid 2-[(2R,3R,4S)-4-(tert-butyldiphenylsilanyloxy)-2,3-(O-isopropylidenedioxy)cyclopent-1⁽⁵⁾enyl]ethyl ester

There total 12 articles about 2,2-dimethylpropionic acid 2-[(2R,3R,4S)-4-(tert-butyldiphenylsilanyloxy)-2,3-(O-isopropylidenedioxy)cyclopent-1⁽⁵⁾enyl]ethyl ester 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: 93.0%

[3-(tert-butyldiphenylsilyloxy)-4,5-(O,O-isopropylidenedihydroxy)-1-cyclopentene-1-yl]ethanol (1373313-90-6) + pivaloyl chloride (3282-30-2) → 2,2-dimethylpropionic acid 2-[(2R,3R,4S)-4-(tert-butyldiphenylsilanyloxy)-2,3-(O-isopropylidenedioxy)cyclopent-1(5)enyl]ethyl ester (1373313-91-7)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 10h; Inert atmosphere;

DOI:10.1021/ol300667q

Reference yield:

(3aS,6S,6aS)-2,2-dimethyl-6-vinyltetrahydrofuro[3,4-d][1,3]dioxol-4-ol → 2,2-dimethylpropionic acid 2-[(2R,3R,4S)-4-(tert-butyldiphenylsilanyloxy)-2,3-(O-isopropylidenedioxy)cyclopent-1(5)enyl]ethyl ester (1373313-91-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: n-butyllithium; lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

1.2: 12.5 h / -78 - 20 °C / Inert atmosphere

1.3: Inert atmosphere

2.1: Grubbs catalyst first generation / dichloromethane / 24 h

3.1: tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

4.1: sodium perborate tetrahydrate / tetrahydrofuran; water / 15 h / 20 °C / Inert atmosphere

5.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 10 h / 0 - 20 °C / Inert atmosphere

With Grubbs catalyst first generation; dmap; n-butyllithium; sodium perborate tetrahydrate; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/ol300667q

Reference yield:

(3aS,4S,6aR)-2,2-dimethyl-6-vinyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-ol (1373313-77-9) → 2,2-dimethylpropionic acid 2-[(2R,3R,4S)-4-(tert-butyldiphenylsilanyloxy)-2,3-(O-isopropylidenedioxy)cyclopent-1(5)enyl]ethyl ester (1373313-91-7)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

2: sodium perborate tetrahydrate / tetrahydrofuran; water / 15 h / 20 °C / Inert atmosphere

3: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 10 h / 0 - 20 °C / Inert atmosphere

With dmap; sodium perborate tetrahydrate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/ol300667q

upstream raw materials:

(3aS,4S,6aR)-2,2-dimethyl-6-vinyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-ol

[3-(tert-butyldiphenylsilyloxy)-4,5-(O,O-isopropylidenedihydroxy)-1-cyclopentene-1-yl]ethanol

pivaloyl chloride

2,3-O-isopropylidene-D-ribofuranose

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