(1R,4R)-4-tert-butyldimethylsilyloxymethyl-4-methyl-3-(2-phenylsulfinylethyl)-2-cycloxenyl but-2-ynoate

Base Information

Chemical Name:(1R,4R)-4-tert-butyldimethylsilyloxymethyl-4-methyl-3-(2-phenylsulfinylethyl)-2-cycloxenyl but-2-ynoate
CAS No.:535932-70-8
Molecular Formula:C₂₆H₃₈O₄SSi
Molecular Weight:474.737
Hs Code.:

Synonyms:(1R,4R)-4-tert-butyldimethylsilyloxymethyl-4-methyl-3-(2-phenylsulfinylethyl)-2-cycloxenyl but-2-ynoate

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Chemical Property of (1R,4R)-4-tert-butyldimethylsilyloxymethyl-4-methyl-3-(2-phenylsulfinylethyl)-2-cycloxenyl but-2-ynoate

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Technology Process of (1R,4R)-4-tert-butyldimethylsilyloxymethyl-4-methyl-3-(2-phenylsulfinylethyl)-2-cycloxenyl but-2-ynoate

There total 2 articles about (1R,4R)-4-tert-butyldimethylsilyloxymethyl-4-methyl-3-(2-phenylsulfinylethyl)-2-cycloxenyl but-2-ynoate 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: 95.0%

: 590-93-2
2-Butynoic acid

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

: 535932-70-8
(1R,4R)-4-tert-butyldimethylsilyloxymethyl-4-methyl-3-(2-phenylsulfinylethyl)-2-cycloxenyl but-2-ynoate

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In toluene; at 0 ℃; for 0.5h;
DOI:10.1021/jo020743y

Reference yield: 91.0%

: 590-93-2
2-Butynoic acid

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

: 535932-70-8
(1R,4R)-4-tert-butyldimethylsilyloxymethyl-4-methyl-3-(2-phenylsulfinylethyl)-2-cycloxenyl but-2-ynoate

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1021/jo020743y

Reference yield:

: 535932-70-8
(1R,4R)-4-tert-butyldimethylsilyloxymethyl-4-methyl-3-(2-phenylsulfinylethyl)-2-cycloxenyl but-2-ynoate

: 535932-84-4
(2aS,3S,5aR,6R,8aR,8bR)-3,6-Dimethyl-6-phenylsulfanylmethyl-decahydro-naphtho[1,8-bc]furan-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 84 percent / ethyl propiolate; pyridine / toluene / 61 h / Heating

2: H₂; PtO₂ / acetic acid / 30 h / 20 °C / 3040 Torr

3: 369 mg / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

4: 79 percent / Bu₃P; pyridine / 1.5 h / 60 °C

With pyridine; platinum(IV) oxide; tributylphosphine; tetrabutyl ammonium fluoride; hydrogen; propynoic acid ethyl ester; In tetrahydrofuran; acetic acid; toluene; 1: intramolecular Diels-Alder reaction;
DOI:10.1021/jo020743y