(E)-(3R,5S)-7-[(1R,5S,6S)-6-(2,2-Dimethyl-butyryloxymethyl)-5-isopropyl-2,2-dimethyl-cyclohexyl]-3,5-dihydroxy-hept-6-enoic acid tert-butyl ester

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Chemical Name:(E)-(3R,5S)-7-[(1R,5S,6S)-6-(2,2-Dimethyl-butyryloxymethyl)-5-isopropyl-2,2-dimethyl-cyclohexyl]-3,5-dihydroxy-hept-6-enoic acid tert-butyl ester
CAS No.:144225-46-7
Molecular Formula:C₂₉H₅₂O₆
Molecular Weight:496.728
Hs Code.:

Synonyms:(E)-(3R,5S)-7-[(1R,5S,6S)-6-(2,2-Dimethyl-butyryloxymethyl)-5-isopropyl-2,2-dimethyl-cyclohexyl]-3,5-dihydroxy-hept-6-enoic acid tert-butyl ester

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Chemical Property of (E)-(3R,5S)-7-[(1R,5S,6S)-6-(2,2-Dimethyl-butyryloxymethyl)-5-isopropyl-2,2-dimethyl-cyclohexyl]-3,5-dihydroxy-hept-6-enoic acid tert-butyl ester

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Technology Process of (E)-(3R,5S)-7-[(1R,5S,6S)-6-(2,2-Dimethyl-butyryloxymethyl)-5-isopropyl-2,2-dimethyl-cyclohexyl]-3,5-dihydroxy-hept-6-enoic acid tert-butyl ester

There total 15 articles about (E)-(3R,5S)-7-[(1R,5S,6S)-6-(2,2-Dimethyl-butyryloxymethyl)-5-isopropyl-2,2-dimethyl-cyclohexyl]-3,5-dihydroxy-hept-6-enoic acid tert-butyl ester 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: 96.3%

: 144225-45-6
2,2-Dimethyl-butyric acid (1S,2R,6S)-2-[(E)-2-((4S,6R)-6-tert-butoxycarbonylmethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-vinyl]-6-isopropyl-3,3-dimethyl-cyclohexylmethyl ester

: 144225-46-7
(E)-(3R,5S)-7-[(1R,5S,6S)-6-(2,2-Dimethyl-butyryloxymethyl)-5-isopropyl-2,2-dimethyl-cyclohexyl]-3,5-dihydroxy-hept-6-enoic acid tert-butyl ester

Guidance literature:: With toluene-4-sulfonic acid; In methanol; water; for 1h; Ambient temperature;
DOI:10.1021/jo00052a031

Reference yield:

: 144225-29-6
Carvomenthon

: 144225-46-7
(E)-(3R,5S)-7-[(1R,5S,6S)-6-(2,2-Dimethyl-butyryloxymethyl)-5-isopropyl-2,2-dimethyl-cyclohexyl]-3,5-dihydroxy-hept-6-enoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 1) LDA, 2) Et₃N / 1) THF, -15 deg C, 15 min, 2) THF, -78 deg C, 1 h

2: 56 percent / ZnCl₂ / CH₂Cl₂; diethyl ether / 2.5 h / -78 °C

4: 35percent HClO₄ / diethyl ether / 3.5 h / Ambient temperature

5: 1) nBuLi / 1) THF, -78 deg C, 1 h, 2) THF, -78 deg C, 1 h

6: 1) LDA / 1) THF, a) -78 deg C, 5 min, b) 0 deg C, 30 min, 2) THF, -78 deg C, 2 h

7: 90 percent / NaOCH₃ / 3 h / Ambient temperature

8: 1) LDA / 1) THF, a) -78 deg C, 30 min, b) -25 deg C, 1 h, 2) THF, -30 deg C, 3 h

10: 89.2 percent / pTsOH / acetone / 3 h / Ambient temperature

11: 100 percent / H₂ / Pd(OH)2/C / ethyl acetate / 4 h / 760 Torr / Ambient temperature

12: 89.5 percent / DMAP / pyridine / 15 h / Ambient temperature

13: 96.3 percent / pTsOH / methanol; H₂O / 1 h / Ambient temperature

With dmap; n-butyllithium; perchloric acid; hydrogen; sodium methylate; toluene-4-sulfonic acid; triethylamine; zinc(II) chloride; lithium diisopropyl amide; palladium dihydroxide; In pyridine; methanol; diethyl ether; dichloromethane; water; ethyl acetate; acetone;
DOI:10.1021/jo00052a031

Reference yield:

: 69153-92-0
(5R)-5-isopropenyl-2,2-dimethylcyclohexanone

: 144225-46-7
(E)-(3R,5S)-7-[(1R,5S,6S)-6-(2,2-Dimethyl-butyryloxymethyl)-5-isopropyl-2,2-dimethyl-cyclohexyl]-3,5-dihydroxy-hept-6-enoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 14 steps

1: 87 percent / H₂ / (Ph₃P)3RhCl / toluene

2: 1) LDA, 2) Et₃N / 1) THF, -15 deg C, 15 min, 2) THF, -78 deg C, 1 h

3: 56 percent / ZnCl₂ / CH₂Cl₂; diethyl ether / 2.5 h / -78 °C

5: 35percent HClO₄ / diethyl ether / 3.5 h / Ambient temperature

6: 1) nBuLi / 1) THF, -78 deg C, 1 h, 2) THF, -78 deg C, 1 h

7: 1) LDA / 1) THF, a) -78 deg C, 5 min, b) 0 deg C, 30 min, 2) THF, -78 deg C, 2 h

8: 90 percent / NaOCH₃ / 3 h / Ambient temperature

9: 1) LDA / 1) THF, a) -78 deg C, 30 min, b) -25 deg C, 1 h, 2) THF, -30 deg C, 3 h

11: 89.2 percent / pTsOH / acetone / 3 h / Ambient temperature

12: 100 percent / H₂ / Pd(OH)2/C / ethyl acetate / 4 h / 760 Torr / Ambient temperature

13: 89.5 percent / DMAP / pyridine / 15 h / Ambient temperature

14: 96.3 percent / pTsOH / methanol; H₂O / 1 h / Ambient temperature

With dmap; n-butyllithium; perchloric acid; hydrogen; sodium methylate; toluene-4-sulfonic acid; triethylamine; zinc(II) chloride; lithium diisopropyl amide; palladium dihydroxide; Wilkinson's catalyst; In pyridine; methanol; diethyl ether; dichloromethane; water; ethyl acetate; acetone; toluene;
DOI:10.1021/jo00052a031