(3S,4S)-3,5-Dihydroxy-1-[(R)-2-((1S,2R)-2-hydroxy-cyclohex-3-enyl)-oxiranyl]-4-methyl-pentan-1-one

Base Information

• Chemical Name: (3S,4S)-3,5-Dihydroxy-1-[(R)-2-((1S,2R)-2-hydroxy-cyclohex-3-enyl)-oxiranyl]-4-methyl-pentan-1-one
• CAS No.: 124603-91-4
• Molecular Formula: C₁₄H₂₂O₅
• Molecular Weight: 270.326
• Mol file: 124603-91-4.mol

Synonyms:(3S,4S)-3,5-Dihydroxy-1-[(R)-2-((1S,2R)-2-hydroxy-cyclohex-3-enyl)-oxiranyl]-4-methyl-pentan-1-one

Chemical Property of (3S,4S)-3,5-Dihydroxy-1-[(R)-2-((1S,2R)-2-hydroxy-cyclohex-3-enyl)-oxiranyl]-4-methyl-pentan-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-3,5-Dihydroxy-1-[(R)-2-((1S,2R)-2-hydroxy-cyclohex-3-enyl)-oxiranyl]-4-methyl-pentan-1-one

There total 8 articles about (3S,4S)-3,5-Dihydroxy-1-[(R)-2-((1S,2R)-2-hydroxy-cyclohex-3-enyl)-oxiranyl]-4-methyl-pentan-1-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%

(3S,4S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-1-[(R)-2-((1S,2R)-2-hydroxy-cyclohex-3-enyl)-oxiranyl]-4-methyl-pentan-1-one (124603-90-3) → (3S,4S)-3,5-Dihydroxy-1-[(R)-2-((1S,2R)-2-hydroxy-cyclohex-3-enyl)-oxiranyl]-4-methyl-pentan-1-one (124603-91-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.166667h;

DOI:10.1021/jo00294a030

Reference yield:

cis-2-<2-<(4-methoxybenzyl)oxy>-3-cyclohexen-1-yl>-2-propen-1-ol (97826-91-0) → (3S,4S)-3,5-Dihydroxy-1-[(R)-2-((1S,2R)-2-hydroxy-cyclohex-3-enyl)-oxiranyl]-4-methyl-pentan-1-one (124603-91-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 3.4 g / (+)-diethyl L-tartrate, titanium(IV) tert-butoxide, t-BuOOH / CH₂Cl₂ / 5.5 h / -23 °C

2: 1. oxalyl chloride, DMSO 2. NEt₃ / 1. CH₂Cl₂, -55 deg C 2. -55 deg C up to 25 deg C

3: 77 percent / tetrahydrofuran / 0.12 h / -78 °C

4: 1. oxalyl chloride, DMSO 2. NEt₃ / 1. CH₂Cl₂, -55 deg C, 1 h 2. -55 deg C up to 25 deg C

5: 1. LDA / 1. THF, -78 deg C, 50 min 2. -78 deg C, 10 min

6: 95 percent / 2,3-dichloro-5,6-dicyano-1,4-benzochinone / CH₂Cl₂; H₂O / 1.5 h

7: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h

With titanium(IV) tetrabutoxide; tert.-butylhydroperoxide; oxalyl dichloride; diethyl (2R,3R)-tartrate; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jo00294a030

Reference yield:

1-{(R)-2-[(1S,2R)-2-(4-Methoxy-benzyloxy)-cyclohex-3-enyl]-oxiranyl}-ethanol (124603-89-0,124649-52-1) → (3S,4S)-3,5-Dihydroxy-1-[(R)-2-((1S,2R)-2-hydroxy-cyclohex-3-enyl)-oxiranyl]-4-methyl-pentan-1-one (124603-91-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 1. oxalyl chloride, DMSO 2. NEt₃ / 1. CH₂Cl₂, -55 deg C, 1 h 2. -55 deg C up to 25 deg C

2: 1. LDA / 1. THF, -78 deg C, 50 min 2. -78 deg C, 10 min

3: 95 percent / 2,3-dichloro-5,6-dicyano-1,4-benzochinone / CH₂Cl₂; H₂O / 1.5 h

4: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h

With oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jo00294a030

upstream raw materials:

(3S,4S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-1-[(R)-2-((1S,2R)-2-hydroxy-cyclohex-3-enyl)-oxiranyl]-4-methyl-pentan-1-one

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

1-{(R)-2-[(1S,2R)-2-(4-Methoxy-benzyloxy)-cyclohex-3-enyl]-oxiranyl}-ethanol

2(R)-<2(R)-<(4-methoxybenzyl)oxy>-3-cyclohexen-1(S)-yl>oxiranecarbaldehyde

Downstream raw materials:

(2R,2'S,3'aR,7'aR,4''S,5''R)-4''-<<4-(diphenylphosphino)benzoyl>oxy>-5''-methyl-3'a,6',7',7'a,3'',4'',5'',6''-octahydrodispiro-pyran>

(2R,2'S,3'aR,7'aR,4''S,5''R)-4''-<<3-(diphenylphosphino)benzoyl>oxy>-5''-methyl-3'a,6',7',7'a,3'',4'',5'',6''-octahydrodispiropyran>

C₃₃H₃₃O₆P

C₃₄H₃₅O₆P