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

Base Information

Chemical Name:3(R)-<1(R)-methyl-2-<(tert-butyldimethylsilyl)oxy>ethyl>-4(S)-methyl-5(R)-<1(S)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>dihydro-2(3H)-furanone
CAS No.:115047-31-9
Molecular Formula:C₃₃H₅₂O₄Si₂
Molecular Weight:568.944
Hs Code.:

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

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

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

There total 7 articles about 3(R)-<1(R)-methyl-2-<(tert-butyldimethylsilyl)oxy>ethyl>-4(S)-methyl-5(R)-<1(S)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>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:

: (3R,4S,5R)-5-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-3-((R)-2-hydroxy-1-methyl-ethyl)-4-methyl-dihydro-furan-2-one

: 18162-48-6
tert-butyldimethylsilyl chloride

: 115047-31-9
3(R)-<1(R)-methyl-2-<(tert-butyldimethylsilyl)oxy>ethyl>-4(S)-methyl-5(R)-<1(S)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>dihydro-2(3H)-furanone

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

Reference yield:

: 110410-94-1
3(R)-(1(S),4-dimethyl-2(E)-pentenyl)-4(S)-methyl-5(R)-<1(S)-methyl-2<(tert-butyldiphenylsilyl)oxy>ethyl>dihydro-2(3H)-furanone

: 115047-31-9
3(R)-<1(R)-methyl-2-<(tert-butyldimethylsilyl)oxy>ethyl>-4(S)-methyl-5(R)-<1(S)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>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: 4-(dimethylamino)pyridine, imidazole / dimethylformamide / 25 °C

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

Reference yield:

: 103576-61-0
4(S)-methyl-5(R)-<1(S)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>-dihydro-2(3H)furanone

: 115047-31-9
3(R)-<1(R)-methyl-2-<(tert-butyldimethylsilyl)oxy>ethyl>-4(S)-methyl-5(R)-<1(S)-methyl-2-<(tert-butyldiphenylsilyl)oxy>ethyl>dihydro-2(3H)-furanone

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) LDA / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, HMPA, -78 deg C, 3 h

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

3: 21 percent / LiCl / H₂O; dimethylsulfoxide / 3 h / 200 °C

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

5: 4-(dimethylamino)pyridine, imidazole / dimethylformamide / 25 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydride; sodium hydrogencarbonate; ozone; triphenylphosphine; lithium chloride; lithium diisopropyl amide; In water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/ja00224a032