(1R,4R)-4-tert-butyldimethylsilyloxymethyl-4-methyl-3-(2-phenylsulfinylethyl)-2-cyclohexenyl propiolate

Base Information

Chemical Name:(1R,4R)-4-tert-butyldimethylsilyloxymethyl-4-methyl-3-(2-phenylsulfinylethyl)-2-cyclohexenyl propiolate
CAS No.:331627-29-3
Molecular Formula:C₂₅H₃₆O₄SSi
Molecular Weight:460.71
Hs Code.:

Synonyms:(1R,4R)-4-tert-butyldimethylsilyloxymethyl-4-methyl-3-(2-phenylsulfinylethyl)-2-cyclohexenyl propiolate

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Chemical Property of (1R,4R)-4-tert-butyldimethylsilyloxymethyl-4-methyl-3-(2-phenylsulfinylethyl)-2-cyclohexenyl propiolate

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Technology Process of (1R,4R)-4-tert-butyldimethylsilyloxymethyl-4-methyl-3-(2-phenylsulfinylethyl)-2-cyclohexenyl propiolate

There total 9 articles about (1R,4R)-4-tert-butyldimethylsilyloxymethyl-4-methyl-3-(2-phenylsulfinylethyl)-2-cyclohexenyl propiolate 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: 100.0%

: 471-25-0
Propiolic acid

: 331627-36-2
(1R,4R)-3-(2-Benzenesulfinyl-ethyl)-4-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-cyclohex-2-enol

: 331627-29-3
(1R,4R)-4-tert-butyldimethylsilyloxymethyl-4-methyl-3-(2-phenylsulfinylethyl)-2-cyclohexenyl propiolate

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In toluene; at 0 ℃; for 1h;
DOI:10.1021/jo0015772

Reference yield: 98.0%

: 471-25-0
Propiolic acid

: 331627-49-7
(1S,4R)-3-(2-Benzenesulfinyl-ethyl)-4-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-cyclohex-2-enol

: 331627-29-3
(1R,4R)-4-tert-butyldimethylsilyloxymethyl-4-methyl-3-(2-phenylsulfinylethyl)-2-cyclohexenyl propiolate

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1021/jo0015772

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 331627-29-3
(1R,4R)-4-tert-butyldimethylsilyloxymethyl-4-methyl-3-(2-phenylsulfinylethyl)-2-cyclohexenyl propiolate

Guidance literature:: Multi-step reaction with 6 steps

1: 94 percent / imidazole / dimethylformamide / 10 h / 20 °C

2: 21.6 g / tetrahydrofuran / 6 h / 0 °C

3: 93 percent / Et₃N / benzene / 1 h / 20 °C

4: 8.75 g / DIBAL-H / toluene / 0.5 h / -78 °C

5: 97 percent / m-CPBA; Na₂HPO₄ / CHCl₃ / 0.5 h / -42 °C

6: 98 percent / DEAD; PPh₃ / tetrahydrofuran / 1 h / 20 °C

With 1H-imidazole; disodium hydrogenphosphate; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; chloroform; N,N-dimethyl-formamide; toluene; benzene; 6: Mitsunobu reaction;
DOI:10.1021/jo0015772