tert-butyl-{(E)-(1S,4S)-6-[(4R)-2-(4-methoxyphenyl)-[1,3]dioxan-4-yl]-1,2,4-trimethyl-hex-2-enyloxy}dimethylsilane

Base Information

Chemical Name:tert-butyl-{(E)-(1S,4S)-6-[(4R)-2-(4-methoxyphenyl)-[1,3]dioxan-4-yl]-1,2,4-trimethyl-hex-2-enyloxy}dimethylsilane
CAS No.:927396-44-9
Molecular Formula:C₂₆H₄₄O₄Si
Molecular Weight:448.718
Hs Code.:

Synonyms:tert-butyl-{(E)-(1S,4S)-6-[(4R)-2-(4-methoxyphenyl)-[1,3]dioxan-4-yl]-1,2,4-trimethyl-hex-2-enyloxy}dimethylsilane

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Chemical Property of tert-butyl-{(E)-(1S,4S)-6-[(4R)-2-(4-methoxyphenyl)-[1,3]dioxan-4-yl]-1,2,4-trimethyl-hex-2-enyloxy}dimethylsilane

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Technology Process of tert-butyl-{(E)-(1S,4S)-6-[(4R)-2-(4-methoxyphenyl)-[1,3]dioxan-4-yl]-1,2,4-trimethyl-hex-2-enyloxy}dimethylsilane

There total 5 articles about tert-butyl-{(E)-(1S,4S)-6-[(4R)-2-(4-methoxyphenyl)-[1,3]dioxan-4-yl]-1,2,4-trimethyl-hex-2-enyloxy}dimethylsilane 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: 86.0%

: 927396-55-2
(E)-(2S,5S)-7-[(4R)-2-(4-methoxyphenyl)-[1,3]dioxan-4-yl]-3,5-dimethyl-hept-3-en-2-ol

: 69739-34-0
t-butyldimethylsiyl triflate

: 927396-44-9
tert-butyl-{(E)-(1S,4S)-6-[(4R)-2-(4-methoxyphenyl)-[1,3]dioxan-4-yl]-1,2,4-trimethyl-hex-2-enyloxy}dimethylsilane

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 2h;
DOI:10.1021/ol062957y

Reference yield:

: 927396-58-5
(S)-4-[(4R)-2-(4-methoxyphenyl)-[1,3]dioxan-4-yl]-2-methylbutyraldehyde

: 927396-44-9
tert-butyl-{(E)-(1S,4S)-6-[(4R)-2-(4-methoxyphenyl)-[1,3]dioxan-4-yl]-1,2,4-trimethyl-hex-2-enyloxy}dimethylsilane

Guidance literature:: Multi-step reaction with 3 steps

1: 0.750 g / Ba(OH)2 / tetrahydrofuran; H₂O / 0.5 h / 20 °C

2: (R)-CBS; catecholborane / toluene / 12 h / -78 °C

3: 86 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

With 2,6-dimethylpyridine; barium dihydroxide; (R)-(+)-2-methyl-CBS-oxazaborolidine; benzo[1,3,2]dioxaborole; In tetrahydrofuran; dichloromethane; water; toluene;
DOI:10.1021/ol062957y

Reference yield:

: 927396-54-1
(S)-4-[(4R)-2-(4-methoxyphenyl)-[1,3]dioxan-4-yl]-2-methylbutan-1-ol

: 927396-44-9
tert-butyl-{(E)-(1S,4S)-6-[(4R)-2-(4-methoxyphenyl)-[1,3]dioxan-4-yl]-1,2,4-trimethyl-hex-2-enyloxy}dimethylsilane

Guidance literature:: Multi-step reaction with 4 steps

1: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 0.5 h / -78 - 20 °C

2: 0.750 g / Ba(OH)2 / tetrahydrofuran; H₂O / 0.5 h / 20 °C

3: (R)-CBS; catecholborane / toluene / 12 h / -78 °C

4: 86 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

With 2,6-dimethylpyridine; barium dihydroxide; oxalyl dichloride; dimethyl sulfoxide; triethylamine; (R)-(+)-2-methyl-CBS-oxazaborolidine; benzo[1,3,2]dioxaborole; In tetrahydrofuran; dichloromethane; water; toluene; 1: Swern oxidation;
DOI:10.1021/ol062957y