(E,3S,4R,5S)-4,6-Dimethyl-5-<(p-methoxybenzyl)oxy>-7-<(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexyl>-6-hepten-1,3-diol

Base Information

Chemical Name:(E,3S,4R,5S)-4,6-Dimethyl-5-<(p-methoxybenzyl)oxy>-7-<(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexyl>-6-hepten-1,3-diol
CAS No.:171011-82-8
Molecular Formula:C₃₃H₅₈O₆Si
Molecular Weight:578.905
Hs Code.:

Synonyms:(E,3S,4R,5S)-4,6-Dimethyl-5-<(p-methoxybenzyl)oxy>-7-<(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexyl>-6-hepten-1,3-diol

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Chemical Property of (E,3S,4R,5S)-4,6-Dimethyl-5-<(p-methoxybenzyl)oxy>-7-<(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexyl>-6-hepten-1,3-diol

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Technology Process of (E,3S,4R,5S)-4,6-Dimethyl-5-<(p-methoxybenzyl)oxy>-7-<(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexyl>-6-hepten-1,3-diol

There total 5 articles about (E,3S,4R,5S)-4,6-Dimethyl-5-<(p-methoxybenzyl)oxy>-7-<(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexyl>-6-hepten-1,3-diol 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: 89.0%

: 171011-81-7
(2E,2R,3R,4S,5S)-4,6-Dimethyl-2,3-epoxy-5-<(p-methoxybenzyl)oxy>-7-<(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexyl>-2,6-heptadien-1-ol

: 171011-82-8
(E,3S,4R,5S)-4,6-Dimethyl-5-<(p-methoxybenzyl)oxy>-7-<(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexyl>-6-hepten-1,3-diol

Guidance literature:: With sodium dihydro-bis-(2-methoxyethoxy)aluminate; In tetrahydrofuran; toluene; at -5 ℃; for 20h;
DOI:10.1021/jo00127a031

Reference yield:

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 171011-82-8
(E,3S,4R,5S)-4,6-Dimethyl-5-<(p-methoxybenzyl)oxy>-7-<(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexyl>-6-hepten-1,3-diol

Guidance literature:: Multi-step reaction with 4 steps

1: triflic acid / diethyl ether / 0.83 h / Ambient temperature

2: 91 percent / bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran; toluene / 15 h / 0 °C

3: 91 percent / molecular sieves, D-(-)-diethyl tartrate, Ti(Oi-Pr)4, TBHP / CH₂Cl₂ / 15 h / -22 °C

4: 89 percent / bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran; toluene / 20 h / -5 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; molecular sieve; diethyl (2S,3S)-tartrate; trifluorormethanesulfonic acid; sodium dihydro-bis-(2-methoxyethoxy)aluminate; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1021/jo00127a031

Reference yield:

: 171011-80-6
(2E,4R,5S,6E)-4,6-Dimethyl-5-<(p-methoxybenzyl)oxy>-7-<(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexyl>-2,6-heptadien-1-ol

: 171011-82-8
(E,3S,4R,5S)-4,6-Dimethyl-5-<(p-methoxybenzyl)oxy>-7-<(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexyl>-6-hepten-1,3-diol

Guidance literature:: Multi-step reaction with 2 steps

1: 91 percent / molecular sieves, D-(-)-diethyl tartrate, Ti(Oi-Pr)4, TBHP / CH₂Cl₂ / 15 h / -22 °C

2: 89 percent / bis(2-methoxyethoxy)aluminium hydride / tetrahydrofuran; toluene / 20 h / -5 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; molecular sieve; diethyl (2S,3S)-tartrate; sodium dihydro-bis-(2-methoxyethoxy)aluminate; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/jo00127a031