tert-butyl (3R,4S,5S,7Z,9S,12E)-4,5-epoxy-3-hydroxy-14-(4-methoxybenzyloxy)-4,8,12-trimethyl-9-(triethylsiloxy)tetradeca-7,12-dienoate

Base Information

Chemical Name:tert-butyl (3R,4S,5S,7Z,9S,12E)-4,5-epoxy-3-hydroxy-14-(4-methoxybenzyloxy)-4,8,12-trimethyl-9-(triethylsiloxy)tetradeca-7,12-dienoate
CAS No.:950598-36-4
Molecular Formula:C₃₅H₅₈O₇Si
Molecular Weight:618.927
Hs Code.:

Synonyms:tert-butyl (3R,4S,5S,7Z,9S,12E)-4,5-epoxy-3-hydroxy-14-(4-methoxybenzyloxy)-4,8,12-trimethyl-9-(triethylsiloxy)tetradeca-7,12-dienoate

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Chemical Property of tert-butyl (3R,4S,5S,7Z,9S,12E)-4,5-epoxy-3-hydroxy-14-(4-methoxybenzyloxy)-4,8,12-trimethyl-9-(triethylsiloxy)tetradeca-7,12-dienoate

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Technology Process of tert-butyl (3R,4S,5S,7Z,9S,12E)-4,5-epoxy-3-hydroxy-14-(4-methoxybenzyloxy)-4,8,12-trimethyl-9-(triethylsiloxy)tetradeca-7,12-dienoate

There total 12 articles about tert-butyl (3R,4S,5S,7Z,9S,12E)-4,5-epoxy-3-hydroxy-14-(4-methoxybenzyloxy)-4,8,12-trimethyl-9-(triethylsiloxy)tetradeca-7,12-dienoate 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: 64.0%

: 950598-37-5
C₃₅H₅₆O₇Si

: 950598-30-8
tert-butyl (3S,4S,5S,7Z,9S,12E)-4,5-epoxy-3-hydroxy-14-(4-methoxybenzyloxy)-4,8,12-trimethyl-9-(triethylsiloxy)tetradeca-7,12-dienoate

: 950598-36-4
tert-butyl (3R,4S,5S,7Z,9S,12E)-4,5-epoxy-3-hydroxy-14-(4-methoxybenzyloxy)-4,8,12-trimethyl-9-(triethylsiloxy)tetradeca-7,12-dienoate

Guidance literature:: With sodium tetrahydroborate; In methanol; at -78 ℃;
DOI:10.1021/ja073952e

Reference yield: 63.0%

: 950598-29-5
(2R,3S,5Z,7S,10E)-2,3-epoxy-12-(4-methoxybenzyloxy)-2,6,10-trimethyl-7-(triethylsiloxy)dodeca-5,10-diene-1-al

: 540-88-5
acetic acid tert-butyl ester

: 950598-30-8
tert-butyl (3S,4S,5S,7Z,9S,12E)-4,5-epoxy-3-hydroxy-14-(4-methoxybenzyloxy)-4,8,12-trimethyl-9-(triethylsiloxy)tetradeca-7,12-dienoate

: 950598-36-4
tert-butyl (3R,4S,5S,7Z,9S,12E)-4,5-epoxy-3-hydroxy-14-(4-methoxybenzyloxy)-4,8,12-trimethyl-9-(triethylsiloxy)tetradeca-7,12-dienoate

Guidance literature:: With lithium diisopropyl amide; In diethyl ether; at -78 ℃;
DOI:10.1021/ja073952e

Reference yield:

: 950598-27-3
C₂₂H₃₀O₄

: 950598-36-4
tert-butyl (3R,4S,5S,7Z,9S,12E)-4,5-epoxy-3-hydroxy-14-(4-methoxybenzyloxy)-4,8,12-trimethyl-9-(triethylsiloxy)tetradeca-7,12-dienoate

Guidance literature:: Multi-step reaction with 8 steps

1: 74 percent / [RuCl₂(=CHPh)(PCy₃)(SIMes)] / CH₂Cl₂ / 40 °C

2: DIBALH / CH₂Cl₂ / -78 °C

3: toluene / 80 °C

4: imidazole / CH₂Cl₂

5: DIBALH / CH₂Cl₂ / -78 °C

6: L-(+)-diethyl tartrate; Ti(i-PrO)4; TBHP / molecular sieves 4 Angstroem / CH₂Cl₂ / -20 °C

7: SO₃*pyridine; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

8: 27 percent / LDA / diethyl ether / -78 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; 4 A molecular sieve; In diethyl ether; dichloromethane; toluene; 3: Wittig reaction / 6: Sharpless asymmetric epoxidation;
DOI:10.1021/ja073952e