(1R,2S,6R)-2,6-dimethyl-4-(phenylsulfonyl)cyclohex-3-ene-1,2-diol 1,2-diacetonide

Base Information

• Chemical Name: (1R,2S,6R)-2,6-dimethyl-4-(phenylsulfonyl)cyclohex-3-ene-1,2-diol 1,2-diacetonide
• CAS No.: 82796-49-4
• Molecular Formula: C₁₇H₂₂O₄S
• Molecular Weight: 322.425
• Mol file: 82796-49-4.mol

Synonyms:(1R,2S,6R)-2,6-dimethyl-4-(phenylsulfonyl)cyclohex-3-ene-1,2-diol 1,2-diacetonide

Chemical Property of (1R,2S,6R)-2,6-dimethyl-4-(phenylsulfonyl)cyclohex-3-ene-1,2-diol 1,2-diacetonide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,6R)-2,6-dimethyl-4-(phenylsulfonyl)cyclohex-3-ene-1,2-diol 1,2-diacetonide

There total 2 articles about (1R,2S,6R)-2,6-dimethyl-4-(phenylsulfonyl)cyclohex-3-ene-1,2-diol 1,2-diacetonide 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:

(1'S,1R,2R,3S,4S,6R)-2,6-dimethyl-3-<(((1'-phenylethyl)amino)carbonyl)oxy>-4-(phenylsulfonyl)cyclohexane-1,2-diol 1,2-acetonide (82769-87-7) → (1R,2S,6R)-2,6-dimethyl-4-(phenylsulfonyl)cyclohex-3-ene-1,2-diol 1,2-diacetonide (82796-49-4)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; Heating;

DOI:10.1021/ja00385a030

Reference yield:

((S)-1-Phenyl-ethyl)-carbamic acid 2,2,3a,7-tetramethyl-5-phenylsulfanyl-hexahydro-benzo[1,3]dioxol-4-yl ester (82769-84-4,82769-85-5) → (1R,2S,6R)-2,6-dimethyl-4-(phenylsulfonyl)cyclohex-3-ene-1,2-diol 1,2-diacetonide (82796-49-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 15.0 g / m-chloroperbenzoic acid / CH₂Cl₂ / 1.) -35 deg C, 10 min, 2.) -35 deg C -> 25 deg C, 1 h

2: 1,8-diazabicyclo<5.4.0>undec-7-ene / tetrahydrofuran / Heating

With 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00385a030

Reference yield:

(1R,2S,6R)-2,6-dimethyl-4-(phenylsulfonyl)cyclohex-3-ene-1,2-diol 1,2-diacetonide (82796-49-4) → (1S,3S,5R,6R,7S,8R,10R,11S,14R,15S,18R)-13,14-dibenzyl-18-(2-(trimethylsilyl)ethoxy)-6,7,10-trihydroxy-5,7,16,17-tetramethyl-2,12-dioxo-13-azatetracyclo<9.7.0.03,8.011,15>octadec-16-ene 6,7-acetonide (82770-13-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) KDA / 1.) THF, 40 min, 2.) -25 deg C, 30 min

2: 1.) potassium tert-butoxide, 2.) ammoniua, lithium / 1.) tert-butyl alcohol, THF, 0 deg C, 5 min, 2.) -78 deg C, 1.5 h

4: 1.) 80percent m-chloroperbenzoic acid, sodium bicarbonate / 1.) methylene chloride, 0 deg C, 25 min, 2.) pyridine, 25 deg C, 3 h

5: 94 percent / methanesulfonic acid, trifluoroacetic acid / CH₂Cl₂ / 2 h / 25 °C

6: 78 percent / 1 h / 25 °C

7: 67 percent / toluene / 36 h / 110 °C

8: 96 percent / potassium tert-butoxide / H₂O; diethyl ether / 20 h / 25 °C

9: 85 percent / pyridinium chlorochromate, sodium acetate / CH₂Cl₂ / 4 h / 25 °C

10: 1.) L-Selectride, 2.) 5percent aq. sodium hydroxide, 30percent hydrogen peroxide / 1.) THF, -78 deg C, 1 h, 2.) 0 deg C, 10 min

With sodium hydroxide; methanesulfonic acid; Diethoxy-methyl-(6-amino-hexylaminomethyl)-silan; potassium tert-butylate; ammonia; dihydrogen peroxide; sodium acetate; lithium; L-Selectride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; trifluoroacetic acid; In diethyl ether; dichloromethane; water; toluene;

DOI:10.1021/ja00385a030

upstream raw materials:

(1'S,1R,2R,3S,4S,6R)-2,6-dimethyl-3-<(((1'-phenylethyl)amino)carbonyl)oxy>-4-(phenylsulfonyl)cyclohexane-1,2-diol 1,2-acetonide

((S)-1-Phenyl-ethyl)-carbamic acid 2,2,3a,7-tetramethyl-5-phenylsulfanyl-hexahydro-benzo[1,3]dioxol-4-yl ester

Downstream raw materials:

(1R,2S,3S,4S,6R)-2,6-dimethyl-4-(phenylsulfonyl)-4-(2-propenyl)-3-<3-(tert-butoxycarbonyl)-2-oxopropyl>cyclohexane-1,2-diol 1,2-diacetonide

(1R,2S,3S,4S,6R)-2,6-dimethyl-4-(phenylsulfonyl)-4-(2-propenyl)-3-<3-((2-(trimethylsilyl)ethoxy)carbonyl)-2-oxopropyl>cyclohexane-1,2-diol 1,2-diacetonide

(3aR,4R,5aS,6R,10aR)-6-Benzoyloxy-2,2,4,10b-tetramethyl-9-oxo-4,5,5a,6,9,10,10a,10b-octahydro-3aH-1,3-dioxa-cyclohepta[e]indene-8-carboxylic acid

C₂₄H₂₈O₇