(S)-3-Benzyloxy-2-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylethynyl]-tetrahydro-pyran-2-ol

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Chemical Name:(S)-3-Benzyloxy-2-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylethynyl]-tetrahydro-pyran-2-ol
CAS No.:440083-07-8
Molecular Formula:C₂₅H₃₈O₅Si
Molecular Weight:446.659
Hs Code.:

Synonyms:(S)-3-Benzyloxy-2-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylethynyl]-tetrahydro-pyran-2-ol

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Chemical Property of (S)-3-Benzyloxy-2-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylethynyl]-tetrahydro-pyran-2-ol

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Technology Process of (S)-3-Benzyloxy-2-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylethynyl]-tetrahydro-pyran-2-ol

There total 9 articles about (S)-3-Benzyloxy-2-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylethynyl]-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: 90.0%

: 175664-08-1
3(S)-(benzyloxy)tetrahydropyran-2-one

: 175664-06-9
(2R,3S)-2-(2',2'-dibromovinyl)-3-(tert-butyldimethylsiloxy)-tetrahydropyran

: 440083-07-8
(S)-3-Benzyloxy-2-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylethynyl]-tetrahydro-pyran-2-ol

Guidance literature:: (2R,3S)-2-(2',2'-dibromovinyl)-3-(tert-butyldimethylsiloxy)-tetrahydropyran; With n-butyllithium; In tetrahydrofuran; at -78 - 40 ℃;

3(S)-(benzyloxy)tetrahydropyran-2-one; In tetrahydrofuran;
DOI:10.1016/S0040-4020(02)00047-9

Reference yield:

: 63598-39-0
(2R,4aR,8aS)-2-phenylhexahydropyrano<3,2-d>-1,3-dioxin

: 440083-07-8
(S)-3-Benzyloxy-2-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylethynyl]-tetrahydro-pyran-2-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 94 percent / DIBAH / CH₂Cl₂ / 30 h / 25 °C

2: 77 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.92 h / -78 °C

3: 77 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 3 h / 0 °C

4: 71 percent / Na₂CO₃ / methanol / 0.5 h / 25 °C

5: 68 percent / pyridinium chlorochromate, sodium acetate / CH₂Cl₂ / 12 h

6: 1.) n-BuLi / 1) THF, , -35 deg C, 1 h; 2) THF, 25 deg C, 1.5 h

With n-butyllithium; oxalyl dichloride; sodium acetate; diisobutylaluminium hydride; sodium carbonate; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In methanol; dichloromethane;
DOI:10.1021/jo950547+

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 440083-07-8
(S)-3-Benzyloxy-2-[(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylethynyl]-tetrahydro-pyran-2-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 92 percent / CSA / dimethylformamide / 4 h / 50 °C

2: 94 percent / DIBAH / CH₂Cl₂ / 30 h / 25 °C

3: 77 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.92 h / -78 °C

4: 77 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 3 h / 0 °C

5: 71 percent / Na₂CO₃ / methanol / 0.5 h / 25 °C

6: 68 percent / pyridinium chlorochromate, sodium acetate / CH₂Cl₂ / 12 h

7: 1.) n-BuLi / 1) THF, , -35 deg C, 1 h; 2) THF, 25 deg C, 1.5 h

With n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; sodium acetate; diisobutylaluminium hydride; sodium carbonate; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo950547+