(+/-)-(3RS,5S)-5-(t-butyldimethylsilyloxymethyl)-5-phenyl-6-methyl-hepta-1,6-dien-3-ol

Base Information

Chemical Name:(+/-)-(3RS,5S)-5-(t-butyldimethylsilyloxymethyl)-5-phenyl-6-methyl-hepta-1,6-dien-3-ol
CAS No.:828916-96-7
Molecular Formula:C₂₁H₃₄O₂Si
Molecular Weight:346.585
Hs Code.:

Synonyms:(+/-)-(3RS,5S)-5-(t-butyldimethylsilyloxymethyl)-5-phenyl-6-methyl-hepta-1,6-dien-3-ol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (+/-)-(3RS,5S)-5-(t-butyldimethylsilyloxymethyl)-5-phenyl-6-methyl-hepta-1,6-dien-3-ol

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Technology Process of (+/-)-(3RS,5S)-5-(t-butyldimethylsilyloxymethyl)-5-phenyl-6-methyl-hepta-1,6-dien-3-ol

There total 4 articles about (+/-)-(3RS,5S)-5-(t-butyldimethylsilyloxymethyl)-5-phenyl-6-methyl-hepta-1,6-dien-3-ol 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: 71.0%

: 1826-67-1
vinyl magnesium bromide

: 828916-95-6
(+/-)-3-(t-butyldimethylsilyloxymethyl)-3-phenyl-4-methyl-pent-4-enal

: 828916-96-7
(+/-)-(3RS,5S)-5-(t-butyldimethylsilyloxymethyl)-5-phenyl-6-methyl-hepta-1,6-dien-3-ol

Guidance literature:: In tetrahydrofuran; at -78 ℃; for 3h;
DOI:10.1002/ardp.200400875

Reference yield:

: 828916-91-2
4-(t-butyldimethylsilyloxy)-3-phenyl-2-methyl-but-2-enoic acid ethyl ester

: 828916-96-7
(+/-)-(3RS,5S)-5-(t-butyldimethylsilyloxymethyl)-5-phenyl-6-methyl-hepta-1,6-dien-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 91 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1 h / -20 °C

2: 78 percent / propionic acid / 135 - 140 °C

3: 98 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 0.5 h / -10 °C

4: 82 percent / pyridinium chlorochromate / CH₂Cl₂ / 4 h / 20 °C

5: 71 percent / tetrahydrofuran / 3 h / -78 °C

With diisobutylaluminium hydride; propionic acid; pyridinium chlorochromate; In tetrahydrofuran; hexane; dichloromethane; 5: Grignard reaction;
DOI:10.1002/ardp.200400875

Reference yield:

: 828916-93-4
(+/-)-3-(t-butyldimethylsilyloxymethyl)-3-phenyl-4-methyl-pent-4-enoic acid ethyl ester

: 828916-96-7
(+/-)-(3RS,5S)-5-(t-butyldimethylsilyloxymethyl)-5-phenyl-6-methyl-hepta-1,6-dien-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 98 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 0.5 h / -10 °C

2: 82 percent / pyridinium chlorochromate / CH₂Cl₂ / 4 h / 20 °C

3: 71 percent / tetrahydrofuran / 3 h / -78 °C

With diisobutylaluminium hydride; pyridinium chlorochromate; In tetrahydrofuran; hexane; dichloromethane; 3: Grignard reaction;
DOI:10.1002/ardp.200400875