[(2R,3S)-2-((S)-2-Benzyloxy-but-3-enyl)-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane

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Chemical Name:[(2R,3S)-2-((S)-2-Benzyloxy-but-3-enyl)-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane
CAS No.:440083-49-8
Molecular Formula:C₂₂H₃₆O₃Si
Molecular Weight:376.612
Hs Code.:

Synonyms:[(2R,3S)-2-((S)-2-Benzyloxy-but-3-enyl)-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane

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Chemical Property of [(2R,3S)-2-((S)-2-Benzyloxy-but-3-enyl)-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane

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Technology Process of [(2R,3S)-2-((S)-2-Benzyloxy-but-3-enyl)-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane

There total 9 articles about [(2R,3S)-2-((S)-2-Benzyloxy-but-3-enyl)-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane 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: 96.0%

: 100-44-7
benzyl chloride

: 245676-77-1
(2'R,3'S,2S)-1-[3'-(tert-butyldimethylsiloxy)tetrahydropyran-2'-yl]but-3-en-2-ol

: 440083-49-8
[(2R,3S)-2-((S)-2-Benzyloxy-but-3-enyl)-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane

Guidance literature:: With 4-diphenylacetoxy-N-methylpiperidine methiodide; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25 ℃; for 6h;
DOI:10.1016/S0040-4020(02)00047-9

Reference yield:

: 125878-02-6
2-((2R,3S)-3-(tert-butyldimethylsiloxy)tetrahydropyran-2-yl)acetaldehyde

: 440083-49-8
[(2R,3S)-2-((S)-2-Benzyloxy-but-3-enyl)-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 7 steps

1: 88 percent / NaH / benzene / 0.25 h / 25 °C

2: 98 percent / DIBALH / diethyl ether / 1.5 h / 0 °C

3: 95 percent / tBuOOH; (+)-DET; 4 Angstroem molecular sieves / CH₂Cl₂ / 12 h / -20 °C

4: 93 percent / Et₃N; 4-DAMP / CH₂Cl₂ / 8 h / 25 °C

5: 97 percent / NaI; NaHCO₃ / butan-2-one / 1 h / 60 °C

6: 99 percent / tBuLi / diethyl ether / 2 h / -78 °C

7: 96 percent / (iPr)2EtN; 4-DAMP / CH₂Cl₂ / 6 h / 25 °C

With tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; 4 A molecular sieve; tert.-butyl lithium; 4-diphenylacetoxy-N-methylpiperidine methiodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; In diethyl ether; dichloromethane; butanone; benzene;
DOI:10.1016/S0040-4020(02)00047-9

Reference yield:

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

: 440083-49-8
[(2R,3S)-2-((S)-2-Benzyloxy-but-3-enyl)-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 9 steps

1.1: 81 percent / n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

2.1: (Sia)2BH / tetrahydrofuran / 12 h / 0 °C

2.2: 88 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 2 h / 0 °C

3.1: 88 percent / NaH / benzene / 0.25 h / 25 °C

4.1: 98 percent / DIBALH / diethyl ether / 1.5 h / 0 °C

5.1: 95 percent / tBuOOH; (+)-DET; 4 Angstroem molecular sieves / CH₂Cl₂ / 12 h / -20 °C

6.1: 93 percent / Et₃N; 4-DAMP / CH₂Cl₂ / 8 h / 25 °C

7.1: 97 percent / NaI; NaHCO₃ / butan-2-one / 1 h / 60 °C

8.1: 99 percent / tBuLi / diethyl ether / 2 h / -78 °C

9.1: 96 percent / (iPr)2EtN; 4-DAMP / CH₂Cl₂ / 6 h / 25 °C

With tert.-butylhydroperoxide; n-butyllithium; diethyl (2R,3R)-tartrate; (Sia)2BH; 4 A molecular sieve; tert.-butyl lithium; 4-diphenylacetoxy-N-methylpiperidine methiodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; In tetrahydrofuran; diethyl ether; dichloromethane; butanone; benzene;
DOI:10.1016/S0040-4020(02)00047-9