(4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-ol

Base Information

Chemical Name:(4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-ol
CAS No.:263369-06-8
Molecular Formula:C₂₂H₃₀O₃Si
Molecular Weight:370.564
Hs Code.:

Synonyms:(4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-ol

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Chemical Property of (4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-ol

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Technology Process of (4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-ol

There total 7 articles about (4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-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: 87.0%

: 263369-05-7
(+)-(3R,5R)-3-(tert-butyldiphenylsilyloxy)-5-hexanolide

: 263369-06-8
(4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-ol

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 0.5h;
DOI:10.1002/(SICI)1099-0690(200001)2000:2<357::AID-EJOC357>3.0.CO;2-N

Reference yield:

: 29736-80-9
3,5-dioxohexanoic acid methyl ester

: 263369-06-8
(4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaH; tert-butyllithium / tetrahydrofuran; pentane / 0 °C

1.2: 70 percent / tetrahydrofuran; pentane / 2 h / 0 °C

2.1: 44 percent / DIBAL / tetrahydrofuran; toluene / 0.5 h / -78 °C

3.1: diethylmethoxyborane / tetrahydrofuran; methanol / 0.75 h / -78 °C

3.2: 90 percent / sodium borohydride / methanol; tetrahydrofuran / 5 h / -78 °C

4.1: 75 percent / Raney nickel / methanol / 6 h

5.1: 83 percent / zinc chloride; 4 Angstroem molecular sieves / tetrahydrofuran / 4 h / Heating

6.1: 87 percent / imidazole / dimethylformamide / 48 h / 20 °C

7.1: 87 percent / DIBAL / CH₂Cl₂; toluene / 0.5 h / -78 °C

With 1H-imidazole; 4 A molecular sieve; diethyl methoxy borane; tert.-butyl lithium; nickel; sodium hydride; diisobutylaluminium hydride; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; pentane; 1.1: deprotonation / 1.2: Substitution / 2.1: Hydrogenation / 3.1: boronation / 3.2: Hydrogenation / 4.1: desulfurization / 5.1: Cyclization / 6.1: Etherification / 7.1: Hydrogenation;
DOI:10.1002/(SICI)1099-0690(200001)2000:2<357::AID-EJOC357>3.0.CO;2-N

Reference yield:

: 121843-07-0
(4R,6R)-4-hydroxy-6-methyltetrahydro-2H-pyran-2-one

: 263369-06-8
(4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 87 percent / imidazole / dimethylformamide / 48 h / 20 °C

2: 87 percent / DIBAL / CH₂Cl₂; toluene / 0.5 h / -78 °C

With 1H-imidazole; diisobutylaluminium hydride; In dichloromethane; N,N-dimethyl-formamide; toluene; 1: Etherification / 2: Hydrogenation;
DOI:10.1002/(SICI)1099-0690(200001)2000:2<357::AID-EJOC357>3.0.CO;2-N