(3S,4S)-4-((4R,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-3-hydroxy-pentanenitrile

Base Information

Chemical Name:(3S,4S)-4-((4R,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-3-hydroxy-pentanenitrile
CAS No.:371978-10-8
Molecular Formula:C₁₆H₂₁NO₃
Molecular Weight:275.348
Hs Code.:

Synonyms:(3S,4S)-4-((4R,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-3-hydroxy-pentanenitrile

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Chemical Property of (3S,4S)-4-((4R,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-3-hydroxy-pentanenitrile

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Technology Process of (3S,4S)-4-((4R,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-3-hydroxy-pentanenitrile

There total 8 articles about (3S,4S)-4-((4R,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-3-hydroxy-pentanenitrile 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: 70.0%

: 151-50-8
potassium cyanide

: 371978-09-5
(1R,2R,3S,4R)-1,2-di-O-isopropylidene-4,5-epoxy-3-methyl-1-phenyl-pentan-1,2-diol

: 371978-10-8
(3S,4S)-4-((4R,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-3-hydroxy-pentanenitrile

Guidance literature:: With lithium perchlorate; In acetonitrile; at 70 ℃; for 6h;
DOI:10.1016/S0040-4020(01)00689-5

Reference yield:

: 211614-45-8
(1R,2R,3E)-5-(tert-butyldiphenylsilyloxy)-1-methoxymethoxy-1-phenyl-pent-3-ene-2-ol

: 371978-10-8
(3S,4S)-4-((4R,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-3-hydroxy-pentanenitrile

Guidance literature:: Multi-step reaction with 6 steps

1.1: 92 percent / conc. HCl / methanol / 48 h / 40 °C

2.1: 91 percent / CuSO₄; p-TsOH / 48 h / 20 °C

3.1: 76 percent / Ti(i-PrO)4; L-(+)-diisopropyltartrate; t-BuOOH / CH₂Cl₂ / 96 h / -20 °C

4.1: 44 percent / hexane; CH₂Cl₂ / 20 h / 20 °C

5.1: SiMe₃Cl; MeC(OMe)3 / CH₂Cl₂ / 1 h / 0 °C

5.2: 65 percent / K₂CO₃ / methanol / 2 h / 20 °C

6.1: 70 percent / LiClO₄ / acetonitrile / 6 h / 70 °C

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; Trimethyl orthoacetate; chloro-trimethyl-silane; L-(+)-diisopropyl tartrate; lithium perchlorate; toluene-4-sulfonic acid; copper(II) sulfate; In methanol; hexane; dichloromethane; acetonitrile;
DOI:10.1016/S0040-4020(01)00689-5

Reference yield:

: 211614-44-7
(1R,2R)-5-(tert-butyldiphenylsilyloxy)-1-methoxymethoxy-1-phenyl-pent-3-yn-2-ol

: 371978-10-8
(3S,4S)-4-((4R,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-3-hydroxy-pentanenitrile

Guidance literature:: Multi-step reaction with 7 steps

1.1: 72 percent / bis(methoxyethoxy) aluminum hydride / diethyl ether; toluene / 5 h / -25 °C

2.1: 92 percent / conc. HCl / methanol / 48 h / 40 °C

3.1: 91 percent / CuSO₄; p-TsOH / 48 h / 20 °C

4.1: 76 percent / Ti(i-PrO)4; L-(+)-diisopropyltartrate; t-BuOOH / CH₂Cl₂ / 96 h / -20 °C

5.1: 44 percent / hexane; CH₂Cl₂ / 20 h / 20 °C

6.1: SiMe₃Cl; MeC(OMe)3 / CH₂Cl₂ / 1 h / 0 °C

6.2: 65 percent / K₂CO₃ / methanol / 2 h / 20 °C

7.1: 70 percent / LiClO₄ / acetonitrile / 6 h / 70 °C

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; Trimethyl orthoacetate; chloro-trimethyl-silane; L-(+)-diisopropyl tartrate; bis(methoxyethoxy) aluminum hydride; lithium perchlorate; toluene-4-sulfonic acid; copper(II) sulfate; In methanol; diethyl ether; hexane; dichloromethane; toluene; acetonitrile;
DOI:10.1016/S0040-4020(01)00689-5