3-Hexen-2-one, 1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-methyl-6-(phenylmethoxy)-, (3E,5S)-

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Chemical Name:3-Hexen-2-one, 1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-methyl-6-(phenylmethoxy)-, (3E,5S)-
CAS No.:881651-46-3
Molecular Formula:C19H26O4
Molecular Weight:318.413
Hs Code.:

Synonyms:

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Chemical Property of 3-Hexen-2-one, 1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-methyl-6-(phenylmethoxy)-, (3E,5S)-

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Technology Process of 3-Hexen-2-one, 1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-methyl-6-(phenylmethoxy)-, (3E,5S)-

There total 1 articles about 3-Hexen-2-one, 1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-methyl-6-(phenylmethoxy)-, (3E,5S)- 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: 86.0%

: 79026-61-2
(R)-3-benzyloxy-2-methylpropanal

: 127929-53-7
Dimethyl (S)-4,5-Isopropylidenedioxy-2-oxopentylphosphonate

: 881651-46-3
(E)-(S)-6-Benzyloxy-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methyl-hex-3-en-2-one

Guidance literature:: Dimethyl (S)-4,5-Isopropylidenedioxy-2-oxopentylphosphonate; With N-ethyl-N,N-diisopropylamine; lithium chloride; In acetonitrile; at 25 ℃; for 2h;

(R)-3-benzyloxy-2-methylpropanal; In acetonitrile; at 25 ℃; for 15h;
DOI:10.1021/ja054750q

Reference yield: 98.0%

: 881651-46-3
(E)-(S)-6-Benzyloxy-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methyl-hex-3-en-2-one

: 881651-47-4
(E)-(2R,5S)-6-Benzyloxy-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methyl-hex-3-en-2-ol

Guidance literature:: With lithium aluminium tetrahydride; lithium iodide; In diethyl ether; at -100 - 0 ℃;
DOI:10.1021/ja054750q

Reference yield:

: 881651-46-3
(E)-(S)-6-Benzyloxy-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-methyl-hex-3-en-2-one

: 881652-16-0
C₃₇H₄₈O₇Si

Guidance literature:: Multi-step reaction with 37 steps

1.1: 98 percent / LiAlH₄; LiI / diethyl ether / -100 - 0 °C

2.1: 97 percent / aq. acetic acid / 5 h / 40 °C

3.1: 70 percent / N-iodosuccinimide; NaHCO₃ / tetrahydrofuran / 36 h / 0 °C

4.1: 99 percent / Et₃N; 4-DMAP / CH₂Cl₂ / 0 - 25 °C

5.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

6.1: 99 percent / H₂ / Raney-Ni / ethanol / 1 h / 25 °C

7.1: 88 percent / H₂ / Pd(OH)2/C / ethanol / 3 h / 25 °C

8.1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 - 25 °C

9.1: Mg / tetrahydrofuran / 2 h / 25 °C

9.2: tetrahydrofuran / 2 h / -78 - 0 °C

10.1: 40.9 g / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 0 - 25 °C

11.1: 98 percent / triethyl orthoformate; p-TsOH / 2.5 h / 55 °C

12.1: 96 percent / TBAF / tetrahydrofuran / 48 h / 25 °C

13.1: 97 percent / Et₃N; 4-DMAP / CH₂Cl₂ / 16 h / 0 - 25 °C

14.1: 98 percent / imidazole; 4-DMAP / CH₂Cl₂ / 0.5 h / 0 °C

15.1: N-methylmorpholine-N-oxide; OsO₄ / 2-methyl-propan-2-ol; H₂O; tetrahydrofuran / 12 h / 25 °C

16.1: 41.5 g / NaIO₄ / 2-methyl-propan-2-ol; H₂O; various solvents / 5 h / 20 °C / pH 7

17.1: n-BuLi / toluene; tetrahydrofuran / 3 h / -30 °C

17.2: tetrahydrofuran; toluene / 1 h / -30 °C

18.1: 13.2 g / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 2 h / 0 °C

19.1: 70 percent / TMSOTf / CH₂Cl₂ / 3 h / -78 - -30 °C

20.1: 95 percent / 4-DMAP; pyridine / CH₂Cl₂ / 3 h / 0 - 25 °C

21.1: 91 percent / 2,6-lutidine; N-bromosuccinimide; H₂O / acetonitrile / 2 h / 25 °C

22.1: 92 percent / NaBH₄ / methanol / 0.08 h / -5 °C

23.1: 56 percent / trifluoroacetic acid / CH₂Cl₂ / 3 h / 0 °C

24.1: 97 percent / imidazole / CH₂Cl₂ / 0.5 h / 0 °C

25.1: 96 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

26.1: oxalyl dichloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

27.1: n-BuLi / tetrahydrofuran; hexane / 1.33 h / -78 - 0 °C

27.2: 145 mg / tetrahydrofuran; hexane / 2.5 h / 0 °C

28.1: 55 percent / Grubb's catalyst 2nd generation / CH₂Cl₂ / 12 h / 40 °C

29.1: 86 percent / HF*py; pyridine / tetrahydrofuran / 2 h / 0 °C

30.1: 88 percent / oxalyl dichloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

31.1: LDA / tetrahydrofuran; hexane / 0.17 h / -78 °C

31.2: 71 percent / N-tert-butylbenzenesulfinimidoyl chloride / tetrahydrofuran; hexane / 0.75 h / -78 °C

32.1: 82 percent / NaBH₄; CeCl₃*7H₂O / methanol / 0.5 h / -65 °C

33.1: 4-DMAP; pyridine / CH₂Cl₂ / 3 h / -10 °C

34.1: 108 mg / Pd₂(dba)3*CHCl₃; n-Bu₃P; LiBH₄ / 1,2-dimethoxy-ethane / 1.5 h / 0 °C

35.1: 72 percent / DIBAL-H / CH₂Cl₂ / 0.33 h / -78 °C

36.1: oxalyl dichloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

37.1: NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 1.5 h / 25 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium chlorite; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; N-Bromosuccinimide; N-iodo-succinimide; osmium(VIII) oxide; lithium aluminium tetrahydride; lithium borohydride; n-butyllithium; cerium(III) chloride; 2-methyl-but-2-ene; oxalyl dichloride; tributylphosphine; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; water; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; pyridine hydrogenfluoride; magnesium; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; orthoformic acid triethyl ester; trifluoroacetic acid; lithium iodide; lithium diisopropyl amide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium dihydroxide; nickel; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; hexane; dichloromethane; various solvents; water; toluene; acetonitrile; tert-butyl alcohol; 26.1: Swern oxidation / 30.1: Swern oxidation / 36.1: Swern oxidation;
DOI:10.1021/ja054750q