(2S,3S,6R)-6-Allyl-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxymethyl-3-methyl-tetrahydro-pyran-4-one

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Chemical Name:(2S,3S,6R)-6-Allyl-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxymethyl-3-methyl-tetrahydro-pyran-4-one
CAS No.:851592-80-8
Molecular Formula:C₂₈H₃₈O₄Si
Molecular Weight:466.693
Hs Code.:

Synonyms:(2S,3S,6R)-6-Allyl-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxymethyl-3-methyl-tetrahydro-pyran-4-one

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Chemical Property of (2S,3S,6R)-6-Allyl-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxymethyl-3-methyl-tetrahydro-pyran-4-one

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Technology Process of (2S,3S,6R)-6-Allyl-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxymethyl-3-methyl-tetrahydro-pyran-4-one

There total 9 articles about (2S,3S,6R)-6-Allyl-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxymethyl-3-methyl-tetrahydro-pyran-4-one 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: 74.0%

: 851592-79-5
acetic acid 1-{1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-but-3-enyloxy}-2-(5-methyl-6H-[1,3]dioxin-4-yl)-ethyl ester

: 851592-80-8
(2S,3S,6R)-6-Allyl-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxymethyl-3-methyl-tetrahydro-pyran-4-one

Guidance literature:: With 2,6-di-tert-butyl-4-methylpyridine; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 2h;
DOI:10.1021/ol050270s

Reference yield:

: 851592-83-1
phenylsulfanyl-acetic acid 1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-but-3-enyl ester

: 851592-80-8
(2S,3S,6R)-6-Allyl-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxymethyl-3-methyl-tetrahydro-pyran-4-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: LDA / tetrahydrofuran; hexane / -78 °C

1.2: 94 percent / tetrahydrofuran; hexane / -78 - -35 °C

2.1: BF₃*OEt₂ / CH₂Cl₂ / 0.25 h / 0 °C

3.1: 91 percent / m-CPBA / CH₂Cl₂ / 0.42 h / -78 °C

4.1: 22 percent / P(OEt)3 / m-xylene / 1 h / Heating

5.1: 76 percent / NaHMDS / tetrahydrofuran / 0.02 h / -78 °C

6.1: DIBAL-H / CH₂Cl₂; hexane / 0.83 h / -78 °C

7.1: 285 mg / pyridine; DMAP / CH₂Cl₂ / 16.5 h / -78 - -10 °C

8.1: 74 percent / TMSOTf; 2,6-di-tert-bytyl-4-methylpyridine / CH₂Cl₂ / 2 h / -78 °C

With pyridine; dmap; 2,6-di-tert-butyl-4-methylpyridine; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; sodium hexamethyldisilazane; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; triethyl phosphite; In tetrahydrofuran; hexane; dichloromethane; m-xylene;
DOI:10.1021/ol050270s

Reference yield:

: 851592-85-3
(5-methyl-[1,3]dioxan-4-ylidene)-acetic acid 1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-but-3-enyl ester

: 851592-80-8
(2S,3S,6R)-6-Allyl-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxymethyl-3-methyl-tetrahydro-pyran-4-one

Guidance literature:: Multi-step reaction with 4 steps

1: 76 percent / NaHMDS / tetrahydrofuran / 0.02 h / -78 °C

2: DIBAL-H / CH₂Cl₂; hexane / 0.83 h / -78 °C

3: 285 mg / pyridine; DMAP / CH₂Cl₂ / 16.5 h / -78 - -10 °C

4: 74 percent / TMSOTf; 2,6-di-tert-bytyl-4-methylpyridine / CH₂Cl₂ / 2 h / -78 °C

With pyridine; dmap; 2,6-di-tert-butyl-4-methylpyridine; trimethylsilyl trifluoromethanesulfonate; sodium hexamethyldisilazane; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol050270s