4(S)-methyl-3(S)-<1(S)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-5(S)-<1(R)-methyl-1-(2,2,5(S)-trimethyldioxan-4(S)-yl)methyl>dihydro-2(3H)-furanone

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Chemical Name:4(S)-methyl-3(S)-<1(S)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-5(S)-<1(R)-methyl-1-(2,2,5(S)-trimethyldioxan-4(S)-yl)methyl>dihydro-2(3H)-furanone
CAS No.:112452-70-7
Molecular Formula:C₃₃H₄₈O₅Si
Molecular Weight:552.827
Hs Code.:

Synonyms:4(S)-methyl-3(S)-<1(S)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-5(S)-<1(R)-methyl-1-(2,2,5(S)-trimethyldioxan-4(S)-yl)methyl>dihydro-2(3H)-furanone

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Chemical Property of 4(S)-methyl-3(S)-<1(S)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-5(S)-<1(R)-methyl-1-(2,2,5(S)-trimethyldioxan-4(S)-yl)methyl>dihydro-2(3H)-furanone

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Technology Process of 4(S)-methyl-3(S)-<1(S)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-5(S)-<1(R)-methyl-1-(2,2,5(S)-trimethyldioxan-4(S)-yl)methyl>dihydro-2(3H)-furanone

There total 8 articles about 4(S)-methyl-3(S)-<1(S)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-5(S)-<1(R)-methyl-1-(2,2,5(S)-trimethyldioxan-4(S)-yl)methyl>dihydro-2(3H)-furanone 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: 87.0%

: 4(S)-methyl-3(S)-(1(S)-methyl-2-hydroxyethyl)-5(S)-<1(R)-methyl-1-(2,2,5(S)-trimethyldioxan-4(S)-yl)methyl>dihydro-2(3H)-furanone

: 58479-61-1
tert-butylchlorodiphenylsilane

: 112452-70-7
4(S)-methyl-3(S)-<1(S)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-5(S)-<1(R)-methyl-1-(2,2,5(S)-trimethyldioxan-4(S)-yl)methyl>dihydro-2(3H)-furanone

Guidance literature:: With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 25 ℃; for 18h;
DOI:10.1021/ja00224a032

Reference yield:

: 112452-69-4
4(S)-methyl-3(S)-(1(R),4-dimethyl-2(E)-pentenyl)-5(S)-<1(R)-methyl-1-(2,2,5(S)-trimethyldioxan-4(S)-yl)methyl>dihydro-2(3H)-furanone

: 112452-70-7
4(S)-methyl-3(S)-<1(S)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-5(S)-<1(R)-methyl-1-(2,2,5(S)-trimethyldioxan-4(S)-yl)methyl>dihydro-2(3H)-furanone

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) ozone, NaHCO₃, 2.) NaBH₄ / 1.) MeOH, CH₂Cl₂, -78 deg C, 2.) MeOH, CH₂Cl₂, -78 deg C, 30 min, 25 deg C, 1 h

2: 87 percent / 4-(dimethylamino)pyridine, imidazole / dimethylformamide / 18 h / 25 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; sodium hydrogencarbonate; ozone; In N,N-dimethyl-formamide;
DOI:10.1021/ja00224a032

Reference yield:

: (3S,4S,5S,6S,7S)-4,6,8-Trihydroxy-3,5,7-trimethyl-octanoic acid

: 112452-70-7
4(S)-methyl-3(S)-<1(S)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-5(S)-<1(R)-methyl-1-(2,2,5(S)-trimethyldioxan-4(S)-yl)methyl>dihydro-2(3H)-furanone

Guidance literature:: Multi-step reaction with 7 steps

1: p-TsOH / 48 h / 25 °C

2: 1.) LDA / 1.) THF, -78 deg C 2.) -78 deg C, 1 h

3: 1.) NaH 2.) Pd(Ph₃P)4, Ph₃P / 1.) THF, 25 deg C, 1.5 h 2.) 0 deg C, (1 h), -25 deg C, (3 h)

4: LiCl, H₂O / dimethylsulfoxide / 3 h / 190 °C

5: t-BuOK / 2-methyl-propan-2-ol; diethyl ether / 25 °C / equilibrium; ratio α/β = 98:2

6: 1.) O₃, NaHCO₃ 2.) NaBH₄ / 1.) MeOH, CH₂Cl₂, -78 deg C 2.) 0 to 25 deg C

7: imidazole, DMAP / dimethylformamide / 18 h / 25 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium tert-butylate; water; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; ozone; triphenylphosphine; lithium chloride; lithium diisopropyl amide; In diethyl ether; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1016/S0040-4039(00)95405-4