(3R,4S)-5<(tert-butyldimethylsilyl)oxy>3-hydroxy-1-<2(R)-<2(R)-<(4-methoxybenzyl)oxy>-3-cyclohexen-1(S)-yl>oxiranyl>-4-methyl-1-pentanone

Base Information

Chemical Name:(3R,4S)-5<(tert-butyldimethylsilyl)oxy>3-hydroxy-1-<2(R)-<2(R)-<(4-methoxybenzyl)oxy>-3-cyclohexen-1(S)-yl>oxiranyl>-4-methyl-1-pentanone
CAS No.:97826-93-2
Molecular Formula:C₂₈H₄₄O₆Si
Molecular Weight:504.739
Hs Code.:

Synonyms:(3R,4S)-5<(tert-butyldimethylsilyl)oxy>3-hydroxy-1-<2(R)-<2(R)-<(4-methoxybenzyl)oxy>-3-cyclohexen-1(S)-yl>oxiranyl>-4-methyl-1-pentanone

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Chemical Property of (3R,4S)-5<(tert-butyldimethylsilyl)oxy>3-hydroxy-1-<2(R)-<2(R)-<(4-methoxybenzyl)oxy>-3-cyclohexen-1(S)-yl>oxiranyl>-4-methyl-1-pentanone

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Technology Process of (3R,4S)-5<(tert-butyldimethylsilyl)oxy>3-hydroxy-1-<2(R)-<2(R)-<(4-methoxybenzyl)oxy>-3-cyclohexen-1(S)-yl>oxiranyl>-4-methyl-1-pentanone

There total 15 articles about (3R,4S)-5<(tert-butyldimethylsilyl)oxy>3-hydroxy-1-<2(R)-<2(R)-<(4-methoxybenzyl)oxy>-3-cyclohexen-1(S)-yl>oxiranyl>-4-methyl-1-pentanone 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:

: 97826-91-0
cis-2-<2-<(4-methoxybenzyl)oxy>-3-cyclohexen-1-yl>-2-propen-1-ol

: 97826-93-2,97905-63-0
(3R,4R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-1-{(R)-2-[(1S,2R)-2-(4-methoxy-benzyloxy)-cyclohex-3-enyl]-oxiranyl}-4-methyl-pentan-1-one

Guidance literature:: Multi-step reaction with 4 steps

1: t-BuOOH, (+)-diethyl tartarate, Ti(O-t-Bu)4 / CH₂Cl₂ / 5.5 h / -23 °C

2: oxalyl chloride / dimethylsulfoxide / -60 °C

3: 2.) oxalyl chloride / 1.) THF, -78 deg C, 6 min, 2.) CH₂Cl₂ -60 deg C

4: 1.) LDA / 1.) THF, -78 deg C, 1 h, 2.) -78 deg C, 10 min

With titanium(IV) tetrabutoxide; tert.-butylhydroperoxide; oxalyl dichloride; (+)-Weinsaeure-diethylester; lithium diisopropyl amide; In dichloromethane; dimethyl sulfoxide;
DOI:10.1021/jo00218a039

Reference yield:

: 97826-90-9
cis-2-(acetyloxy)-1-<2-<(4-methoxybenzyl)oxy>-3-cyclohexen-1-yl>ethanone

: 97826-93-2,97905-63-0
(3R,4R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-1-{(R)-2-[(1S,2R)-2-(4-methoxy-benzyloxy)-cyclohex-3-enyl]-oxiranyl}-4-methyl-pentan-1-one

Guidance literature:: Multi-step reaction with 6 steps

1: tetrahydrofuran / -100 °C

2: K₂CO₃ / methanol / 25 °C

3: t-BuOOH, (+)-diethyl tartarate, Ti(O-t-Bu)4 / CH₂Cl₂ / 5.5 h / -23 °C

4: oxalyl chloride / dimethylsulfoxide / -60 °C

5: 2.) oxalyl chloride / 1.) THF, -78 deg C, 6 min, 2.) CH₂Cl₂ -60 deg C

6: 1.) LDA / 1.) THF, -78 deg C, 1 h, 2.) -78 deg C, 10 min

With titanium(IV) tetrabutoxide; tert.-butylhydroperoxide; oxalyl dichloride; potassium carbonate; (+)-Weinsaeure-diethylester; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/jo00218a039

Reference yield:

: 97905-62-9
2(S)-<2(R)-<(4-methoxybenzyl)oxy>-3-cyclohexen-1(S)-yl>oxiranemethanol

: 97826-93-2,97905-63-0
(3R,4R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-1-{(R)-2-[(1S,2R)-2-(4-methoxy-benzyloxy)-cyclohex-3-enyl]-oxiranyl}-4-methyl-pentan-1-one

Guidance literature:: Multi-step reaction with 3 steps

1: oxalyl chloride / dimethylsulfoxide / -60 °C

2: 2.) oxalyl chloride / 1.) THF, -78 deg C, 6 min, 2.) CH₂Cl₂ -60 deg C

3: 1.) LDA / 1.) THF, -78 deg C, 1 h, 2.) -78 deg C, 10 min

With oxalyl dichloride; lithium diisopropyl amide; In dimethyl sulfoxide;
DOI:10.1021/jo00218a039