(3S,5R)-6-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-5-methyl-1-hexenol

Base Information

Chemical Name:(3S,5R)-6-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-5-methyl-1-hexenol
CAS No.:214533-00-3
Molecular Formula:C₃₁H₄₂O₄Si
Molecular Weight:506.758
Hs Code.:

Synonyms:

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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 (3S,5R)-6-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-5-methyl-1-hexenol

Chemical Property:

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Technology Process of (3S,5R)-6-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-5-methyl-1-hexenol

There total 11 articles about (3S,5R)-6-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-5-methyl-1-hexenol 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:

: tert-Butyl-{(R)-3-[(S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-2-methyl-propoxy}-diphenyl-silane

: 214533-00-3
(3S,5R)-6-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-5-methyl-1-hexenol

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 1.5h; Yield given;
DOI:10.1248/cpb.46.1199

Reference yield:

: 95514-04-8
(R)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol

: 214533-00-3
(3S,5R)-6-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-5-methyl-1-hexenol

Guidance literature:: Multi-step reaction with 9 steps

1: 100 percent / p-dimethylaminopyridine / CH₂Cl₂ / 5 h / Ambient temperature

2: 92 percent / dimethylsulfoxide / 2 h / 50 °C

3: 1.) DIBAH, 2.) aq. HCl, Rochelle salt / 1.) CH₂Cl₂, THF, -78 deg C, 40 min, 2.) CH₂Cl₂, THF, Et₂O, RT, 12 h

4: CH₂Cl₂ / 10 h / Ambient temperature

5: 100 percent / DIBAH / CH₂Cl₂ / 1.5 h / -78 °C

6: 90 percent / (iso-PrO)4Ti, L-(+)-DET, 3A molecular sieves, tert-butylhydroperoxide / CH₂Cl₂; toluene / 8 h / Ambient temperature

7: 98 percent / sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran / 30 h / -20 °C

8: p-TsOH*H₂O / benzene / 3 h / Ambient temperature

9: DIBAH / CH₂Cl₂ / 1.5 h / -78 °C

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; diethyl (2R,3R)-tartrate; 3 A molecular sieve; diisobutylaluminium hydride; toluene-4-sulfonic acid; rochelle salt; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene; benzene;
DOI:10.1248/cpb.46.1199

Reference yield:

: 95514-03-7
(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionic acid methyl ester

: 214533-00-3
(3S,5R)-6-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)-5-methyl-1-hexenol

Guidance literature:: Multi-step reaction with 10 steps

1: Ca(BH₄)2 / ethanol / 15 h / Ambient temperature

2: 100 percent / p-dimethylaminopyridine / CH₂Cl₂ / 5 h / Ambient temperature

3: 92 percent / dimethylsulfoxide / 2 h / 50 °C

4: 1.) DIBAH, 2.) aq. HCl, Rochelle salt / 1.) CH₂Cl₂, THF, -78 deg C, 40 min, 2.) CH₂Cl₂, THF, Et₂O, RT, 12 h

5: CH₂Cl₂ / 10 h / Ambient temperature

6: 100 percent / DIBAH / CH₂Cl₂ / 1.5 h / -78 °C

7: 90 percent / (iso-PrO)4Ti, L-(+)-DET, 3A molecular sieves, tert-butylhydroperoxide / CH₂Cl₂; toluene / 8 h / Ambient temperature

8: 98 percent / sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran / 30 h / -20 °C

9: p-TsOH*H₂O / benzene / 3 h / Ambient temperature

10: DIBAH / CH₂Cl₂ / 1.5 h / -78 °C

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; calcium borohydride; diethyl (2R,3R)-tartrate; 3 A molecular sieve; diisobutylaluminium hydride; toluene-4-sulfonic acid; rochelle salt; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; toluene; benzene;
DOI:10.1248/cpb.46.1199