(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-(2R,3aR,7aS)-hexahydro-furo[3,2-b]pyran-2-yl-ethanol

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Chemical Name:(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-(2R,3aR,7aS)-hexahydro-furo[3,2-b]pyran-2-yl-ethanol
CAS No.:197219-47-9
Molecular Formula:C₂₅H₃₄O₄Si
Molecular Weight:426.628
Hs Code.:

Synonyms:(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-(2R,3aR,7aS)-hexahydro-furo[3,2-b]pyran-2-yl-ethanol

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Chemical Property of (S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-(2R,3aR,7aS)-hexahydro-furo[3,2-b]pyran-2-yl-ethanol

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Technology Process of (S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-(2R,3aR,7aS)-hexahydro-furo[3,2-b]pyran-2-yl-ethanol

There total 13 articles about (S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-(2R,3aR,7aS)-hexahydro-furo[3,2-b]pyran-2-yl-ethanol 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: 47.0%

: 197219-44-6
(4R,5R,7S,8S)-1-bromo-9-(tert-butyldiphenylsilyloxy)-4,5,7,8-diepoxynonane

: 197219-47-9
(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-(2R,3aR,7aS)-hexahydro-furo[3,2-b]pyran-2-yl-ethanol

Guidance literature:: With water; silver trifluoromethanesulfonate; In tetrahydrofuran; at 25 ℃; for 4h;
DOI:10.1016/S0040-4020(97)00780-1

Reference yield: 32.0%

: 197219-44-6
(4R,5R,7S,8S)-1-bromo-9-(tert-butyldiphenylsilyloxy)-4,5,7,8-diepoxynonane

: 197219-47-9
(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-(2R,3aR,7aS)-hexahydro-furo[3,2-b]pyran-2-yl-ethanol

: (2R,3S)-2-[(2S,3S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-oxiranylmethyl]-tetrahydro-pyran-3-ol

Guidance literature:: With water; silver trifluoromethanesulfonate; In tetrahydrofuran; at 25 ℃; for 1h;
DOI:10.1016/S0040-4020(97)00780-1

Reference yield:

: 197219-35-5
6-[(4-methoxyphenyl)methoxy]-(E)-2-hexen-1-ol

: 197219-47-9
(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-(2R,3aR,7aS)-hexahydro-furo[3,2-b]pyran-2-yl-ethanol

Guidance literature:: Multi-step reaction with 10 steps

1.1: 90 percent / Ph₃P; CBr₄ / CH₂Cl₂ / 0.08 h / 0 - 25 °C

2.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 54 percent / tetrahydrofuran; hexane / 7 h / -78 - 25 °C

3.1: 100 percent / MeOH; p-toluenesulfonic acid monohydrate / 0.5 h / 25 °C

4.1: 94 percent / LiAlH₄ / tetrahydrofuran / 13 h / 0 - 25 °C

5.1: 94 percent / (+)-diethyl tartrate; MS₄A; tert-butyl hydroperoxide / Ti(OiPr)4 / CH₂Cl₂; toluene / 15 h / -25 °C

6.1: 100 percent / imidazole / dimethylformamide / 14 h / 0 - 25 °C

7.1: 100 percent / dichlorodicyanobenzoquinone / CH₂Cl₂; H₂O / 1.5 h / 0 - 25 °C

8.1: 81 percent / triphenylphosphine; carbon tetrabromide / CH₂Cl₂ / 0.08 h / 25 °C

9.1: disodium hydrogen phosphate; m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / 0 - 25 °C

10.1: 47 percent / AgOTf; H₂O / tetrahydrofuran / 4 h / 25 °C

With 1H-imidazole; methanol; tert.-butylhydroperoxide; disodium hydrogenphosphate; lithium aluminium tetrahydride; n-butyllithium; carbon tetrabromide; water; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; (+)-Weinsaeure-diethylester; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; titanium(IV) isopropylate; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1.1: Bromination / 2.1: Metallation / 2.2: Alkylation / 3.1: methanolysis / 4.1: Reduction / 5.1: Sharpless epoxidation / 6.1: silylation / 7.1: Oxidation / 8.1: Bromination / 9.1: Epoxidation / 10.1: Cyclization;
DOI:10.1016/S0040-4020(97)00780-1