{(4R,6S)-6-[(E)-2-((1R,5S,6S)-6-Hydroxymethyl-5-isopropyl-2,2-dimethyl-cyclohexyl)-vinyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-acetic acid tert-butyl ester

Base Information

Chemical Name:{(4R,6S)-6-[(E)-2-((1R,5S,6S)-6-Hydroxymethyl-5-isopropyl-2,2-dimethyl-cyclohexyl)-vinyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-acetic acid tert-butyl ester
CAS No.:144225-44-5
Molecular Formula:C₂₆H₄₆O₅
Molecular Weight:438.648
Hs Code.:

Synonyms:{(4R,6S)-6-[(E)-2-((1R,5S,6S)-6-Hydroxymethyl-5-isopropyl-2,2-dimethyl-cyclohexyl)-vinyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-acetic acid tert-butyl ester

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Chemical Property of {(4R,6S)-6-[(E)-2-((1R,5S,6S)-6-Hydroxymethyl-5-isopropyl-2,2-dimethyl-cyclohexyl)-vinyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-acetic acid tert-butyl ester

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Technology Process of {(4R,6S)-6-[(E)-2-((1R,5S,6S)-6-Hydroxymethyl-5-isopropyl-2,2-dimethyl-cyclohexyl)-vinyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-acetic acid tert-butyl ester

There total 12 articles about {(4R,6S)-6-[(E)-2-((1R,5S,6S)-6-Hydroxymethyl-5-isopropyl-2,2-dimethyl-cyclohexyl)-vinyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-acetic 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:

: 144225-29-6
Carvomenthon

: 144225-44-5
{(4R,6S)-6-[(E)-2-((1R,5S,6S)-6-Hydroxymethyl-5-isopropyl-2,2-dimethyl-cyclohexyl)-vinyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-acetic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 11 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

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

Reference yield:

: 144225-31-0
(5S,6R)-6-Benzyloxymethyl-5-isopropyl-2,2-dimethyl-cyclohexanone

: 144225-44-5
{(4R,6S)-6-[(E)-2-((1R,5S,6S)-6-Hydroxymethyl-5-isopropyl-2,2-dimethyl-cyclohexyl)-vinyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-acetic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 9 steps

2: 35percent HClO₄ / diethyl ether / 3.5 h / Ambient temperature

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

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

5: 90 percent / NaOCH₃ / 3 h / Ambient temperature

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

8: 89.2 percent / pTsOH / acetone / 3 h / Ambient temperature

9: 100 percent / H₂ / Pd(OH)2/C / ethyl acetate / 4 h / 760 Torr / Ambient temperature

With n-butyllithium; perchloric acid; hydrogen; sodium methylate; toluene-4-sulfonic acid; lithium diisopropyl amide; palladium dihydroxide; In diethyl ether; ethyl acetate; acetone;
DOI:10.1021/jo00052a031

Reference yield:

: 144225-30-9
((S)-3-Isopropyl-6,6-dimethyl-cyclohex-1-enyloxy)-trimethyl-silane

: 144225-44-5
{(4R,6S)-6-[(E)-2-((1R,5S,6S)-6-Hydroxymethyl-5-isopropyl-2,2-dimethyl-cyclohexyl)-vinyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-acetic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 56 percent / ZnCl₂ / CH₂Cl₂; diethyl ether / 2.5 h / -78 °C

3: 35percent HClO₄ / diethyl ether / 3.5 h / Ambient temperature

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

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

6: 90 percent / NaOCH₃ / 3 h / Ambient temperature

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

9: 89.2 percent / pTsOH / acetone / 3 h / Ambient temperature

10: 100 percent / H₂ / Pd(OH)2/C / ethyl acetate / 4 h / 760 Torr / Ambient temperature

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