(1R,2S,7R,8S,9R,10R)-tert-buyl 2-(benzaoyloxy)-8,9-dihydroxy-8,10-dimethyl-5-oxobicyclo<5.4.0>undeca-3-ene-4-carboxylate 8,9-acetonide

Base Information

• Chemical Name: (1R,2S,7R,8S,9R,10R)-tert-buyl 2-(benzaoyloxy)-8,9-dihydroxy-8,10-dimethyl-5-oxobicyclo<5.4.0>undeca-3-ene-4-carboxylate 8,9-acetonide
• CAS No.: 82796-53-0
• Molecular Formula: C₂₈H₃₆O₇
• Molecular Weight: 484.59
• Mol file: 82796-53-0.mol

Synonyms:(1R,2S,7R,8S,9R,10R)-tert-buyl 2-(benzaoyloxy)-8,9-dihydroxy-8,10-dimethyl-5-oxobicyclo<5.4.0>undeca-3-ene-4-carboxylate 8,9-acetonide

Chemical Property of (1R,2S,7R,8S,9R,10R)-tert-buyl 2-(benzaoyloxy)-8,9-dihydroxy-8,10-dimethyl-5-oxobicyclo<5.4.0>undeca-3-ene-4-carboxylate 8,9-acetonide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,7R,8S,9R,10R)-tert-buyl 2-(benzaoyloxy)-8,9-dihydroxy-8,10-dimethyl-5-oxobicyclo<5.4.0>undeca-3-ene-4-carboxylate 8,9-acetonide

There total 6 articles about (1R,2S,7R,8S,9R,10R)-tert-buyl 2-(benzaoyloxy)-8,9-dihydroxy-8,10-dimethyl-5-oxobicyclo<5.4.0>undeca-3-ene-4-carboxylate 8,9-acetonide 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:

((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,7R,8S,9R,10R)-tert-buyl 2-(benzaoyloxy)-8,9-dihydroxy-8,10-dimethyl-5-oxobicyclo<5.4.0>undeca-3-ene-4-carboxylate 8,9-acetonide (82796-53-0)

Guidance literature:

Multi-step reaction with 6 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

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

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

6: 1.) 80percent m-chloroperbenzoic acid, sodium bicarbonate / 1.) methylene chloride, 0 deg C, 0.5 h, 2.) 25 deg C, 3 h

With Diethoxy-methyl-(6-amino-hexylaminomethyl)-silan; potassium tert-butylate; ammonia; lithium; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00385a030

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,7R,8S,9R,10R)-tert-buyl 2-(benzaoyloxy)-8,9-dihydroxy-8,10-dimethyl-5-oxobicyclo<5.4.0>undeca-3-ene-4-carboxylate 8,9-acetonide (82796-53-0)

Guidance literature:

Multi-step reaction with 5 steps

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

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

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

5: 1.) 80percent m-chloroperbenzoic acid, sodium bicarbonate / 1.) methylene chloride, 0 deg C, 0.5 h, 2.) 25 deg C, 3 h

With Diethoxy-methyl-(6-amino-hexylaminomethyl)-silan; potassium tert-butylate; ammonia; lithium; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran;

DOI:10.1021/ja00385a030

Reference yield:

(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 (82769-94-6) → (1R,2S,7R,8S,9R,10R)-tert-buyl 2-(benzaoyloxy)-8,9-dihydroxy-8,10-dimethyl-5-oxobicyclo<5.4.0>undeca-3-ene-4-carboxylate 8,9-acetonide (82796-53-0)

Guidance literature:

Multi-step reaction with 3 steps

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

3: 1.) 80percent m-chloroperbenzoic acid, sodium bicarbonate / 1.) methylene chloride, 0 deg C, 0.5 h, 2.) 25 deg C, 3 h

With potassium tert-butylate; ammonia; lithium; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid;

DOI:10.1021/ja00385a030

upstream raw materials:

benzoyl chloride

(1R,7S,9R,10R,11S)-tert-butyl 3,10,11-trihydroxy-9,11-dimethylbicyclo<5.4.0>undeca-3,5-diene-4-carboxylate 10,11-acetonide

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