(4S)-3-[(E)-(2S,3S)-3-(tert-butyldiphenylsilanoxy)-2-methyl-1-oxo-4-hexen-1-yl]-4-(phenylmethyl)-1,3-oxazolidin-2-one

Base Information

Chemical Name:(4S)-3-[(E)-(2S,3S)-3-(tert-butyldiphenylsilanoxy)-2-methyl-1-oxo-4-hexen-1-yl]-4-(phenylmethyl)-1,3-oxazolidin-2-one
CAS No.:343262-81-7
Molecular Formula:C₃₃H₃₉NO₄Si
Molecular Weight:541.762
Hs Code.:

Synonyms:(4S)-3-[(E)-(2S,3S)-3-(tert-butyldiphenylsilanoxy)-2-methyl-1-oxo-4-hexen-1-yl]-4-(phenylmethyl)-1,3-oxazolidin-2-one

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Chemical Property of (4S)-3-[(E)-(2S,3S)-3-(tert-butyldiphenylsilanoxy)-2-methyl-1-oxo-4-hexen-1-yl]-4-(phenylmethyl)-1,3-oxazolidin-2-one

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Technology Process of (4S)-3-[(E)-(2S,3S)-3-(tert-butyldiphenylsilanoxy)-2-methyl-1-oxo-4-hexen-1-yl]-4-(phenylmethyl)-1,3-oxazolidin-2-one

There total 1 articles about (4S)-3-[(E)-(2S,3S)-3-(tert-butyldiphenylsilanoxy)-2-methyl-1-oxo-4-hexen-1-yl]-4-(phenylmethyl)-1,3-oxazolidin-2-one 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: 99.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 251318-99-7
(S)-4-Benzyl-3-((E)-(2S,3R)-3-hydroxy-2-methyl-hex-4-enoyl)-oxazolidin-2-one

: 343262-81-7
(4S)-3-[(E)-(2S,3S)-3-(tert-butyldiphenylsilanoxy)-2-methyl-1-oxo-4-hexen-1-yl]-4-(phenylmethyl)-1,3-oxazolidin-2-one

Guidance literature:: With 1H-imidazole; In dichloromethane; for 20h;
DOI:10.1021/ol015753k

Reference yield: 86.0%

: 343262-81-7
(4S)-3-[(E)-(2S,3S)-3-(tert-butyldiphenylsilanoxy)-2-methyl-1-oxo-4-hexen-1-yl]-4-(phenylmethyl)-1,3-oxazolidin-2-one

: 343262-82-8
(E)-(2R,3R)-3-(tert-butyldiphenylsilanoxy)-2-methylhex-4-en-1-ol

Guidance literature:: With lithium borohydride; In diethyl ether; water; at -20 - 5 ℃;
DOI:10.1021/ol015753k

Reference yield:

: 343262-81-7
(4S)-3-[(E)-(2S,3S)-3-(tert-butyldiphenylsilanoxy)-2-methyl-1-oxo-4-hexen-1-yl]-4-(phenylmethyl)-1,3-oxazolidin-2-one

: 343262-60-2
2,2-dimethylpropionic acid 2S-hydroxy-2-(E)-[4S-(4-methoxybenzyloxy)-5R-methyl-6R-propenyltetrahydropyran-2R-yl]ethyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 86 percent / LiBH₄ / diethyl ether; H₂O / -20 - 5 °C

2: 98 percent / dimethylsulfoxide; oxalyl chloride; triethylamine / CH₂Cl₂ / -78 - -30 °C

3: 85 percent / diethyl ether / 3 h / -78 °C

4: 67 percent / CSA / CH₂Cl₂ / 40 h

5: 74 percent / AD-mix-α / 2-methyl-propan-2-ol; H2O / 20 h

6: 100 percent / NaIO₄ / H₂O; tetrahydrofuran / 0.5 h

7: 88 percent / CH₂Cl₂ / 1.5 h

8: 96 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

9: 95 percent / TBHP; Ti(OiPr)4; diethyl-L-tartrate / CH₂Cl₂ / 0.67 h

10: 95 percent / pyridine / CH₂Cl₂ / 5 h / 20 °C

11: 82 percent / TBAF / tetrahydrofuran / 24 h / 40 °C

12: 90 percent / CSA / CH₂Cl₂ / 4 h

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; AD-mix-α; lithium borohydride; oxalyl dichloride; diethyl (2R,3R)-tartrate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; tert-butyl alcohol; 2: Swern oxidation / 7: Wittig olefination;
DOI:10.1021/ol015753k