(3R,5R)-3,4,5-triacetoxycyclohexanone

Base Information

Chemical Name:(3R,5R)-3,4,5-triacetoxycyclohexanone
CAS No.:50459-21-7
Molecular Formula:C₁₂H₁₆O₇
Molecular Weight:272.255
Hs Code.:

Synonyms:(3R,5R)-3,4,5-triacetoxycyclohexanone

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Chemical Property of (3R,5R)-3,4,5-triacetoxycyclohexanone

Chemical Property:

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Technology Process of (3R,5R)-3,4,5-triacetoxycyclohexanone

There total 9 articles about (3R,5R)-3,4,5-triacetoxycyclohexanone 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: 85.0%

: 140363-98-0
(1R,2S,3R,5R)-1,2,3-triacetoxycyclohexan-5-ol

: 50459-21-7
(3R,5R)-3,4,5-triacetoxycyclohexanone

Guidance literature:: With ruthenium(IV) oxide; sodium periodate; In tetrachloromethane; water; for 4h; Ambient temperature;
DOI:10.1016/S0957-4166(00)80209-8

Reference yield:

: 130256-34-7,131321-51-2
meso-1,3-cis,3,5-cis-1,3-diacetoxy-5-benzyloxycyclohexane

: 50459-21-7
(3R,5R)-3,4,5-triacetoxycyclohexanone

Guidance literature:: Multi-step reaction with 9 steps

1: 0.1 M phosphate buffer / 0.17 h / 30 °C / pH 7.0, porcine liver esterase

2: 92 percent / Swern oxidation

3: 90 percent / NaBH₄, CeCl₃ / methanol / 2 h / -20 °C

4: 87 percent / diethyl azodicarboxylate, PPh₃ / tetrahydrofuran / 8 h / Ambient temperature

5: 82 percent / K₂CO₃ / methanol

6: 99 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 20 h / Ambient temperature

7: 1.) 80percent aq. AcOH, 2.) 4-dimethylaminopyridine, pyridine / 1.) RT, 22 h, 2.) RT, 22 h

8: 90 percent / H₂ / 10percent Pd-C / CHCl₃

9: 85 percent / NaIO₄, RuO₂ / CCl₄; H₂O / 4 h / Ambient temperature

With pyridine; dmap; ruthenium(IV) oxide; sodium tetrahydroborate; sodium periodate; phosphate buffer; cerium(III) chloride; hydrogen; potassium carbonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; chloroform; water;
DOI:10.1016/S0957-4166(00)80209-8

Reference yield:

: 131245-94-8
(S)-5-benzyloxy-2-cyclohexen-1-one

: 50459-21-7
(3R,5R)-3,4,5-triacetoxycyclohexanone

Guidance literature:: Multi-step reaction with 7 steps

1: 90 percent / NaBH₄, CeCl₃ / methanol / 2 h / -20 °C

2: 87 percent / diethyl azodicarboxylate, PPh₃ / tetrahydrofuran / 8 h / Ambient temperature

3: 82 percent / K₂CO₃ / methanol

4: 99 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 20 h / Ambient temperature

5: 1.) 80percent aq. AcOH, 2.) 4-dimethylaminopyridine, pyridine / 1.) RT, 22 h, 2.) RT, 22 h

6: 90 percent / H₂ / 10percent Pd-C / CHCl₃

7: 85 percent / NaIO₄, RuO₂ / CCl₄; H₂O / 4 h / Ambient temperature

With pyridine; dmap; ruthenium(IV) oxide; sodium tetrahydroborate; sodium periodate; cerium(III) chloride; hydrogen; potassium carbonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; chloroform; water;
DOI:10.1016/S0957-4166(00)80209-8