4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-one

Base Information

Chemical Name:4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-one
CAS No.:878132-00-4
Molecular Formula:C₃₀H₄₆O₄Si₂
Molecular Weight:526.864
Hs Code.:

4-(<i>tert</i>-butyl-dimethyl-silanyloxy)-6-[2-(<i>tert</i>-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-one

Synonyms:4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-one

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Chemical Property of 4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-one

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Technology Process of 4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-one

There total 1 articles about 4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-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: 91.0%

: (3S,4R,6R)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-3-methyl-tetrahydro-pyran-2-one

: 69739-34-0
t-butyldimethylsiyl triflate

: 878132-00-4
4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-one

Guidance literature:: With 2,6-dimethylpyridine; In N,N-dimethyl-formamide; at 20 ℃; for 3.5h;
DOI:10.1021/ol0527678

Reference yield: 90.0%

: 878132-00-4
4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-one

: 66222-28-4
(benzyloxymethyl)tributylstannane

: 878132-01-5
2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-ol

Guidance literature:: With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 3h;
DOI:10.1021/ol0527678

Reference yield:

: 878132-00-4
4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-one

: 878132-05-9
(2E,4Z)-5-{(2S,3R,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-methyl-tetrahydro-pyran-2-yl}-4-methyl-penta-2,4-dienoic acid ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 90 percent / nBuLi / tetrahydrofuran; hexane / 3 h / -78 °C

2: 90 percent / Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / 1.5 h / -30 °C

3: 100 percent / H₂ / Pd/C / ethanol / 48 h

4: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

5: 88 percent / NaI; DBU / tetrahydrofuran / 1.75 h / -78 - 0 °C

6: 98 percent / DIBALH / CH₂Cl₂; hexane / 0.17 h / -78 °C

7: 99 percent / MnO₂ / CH₂Cl₂; benzene / 24 h / 20 °C

8: 94 percent / toluene / 43 h / 130 °C

With triethylsilane; manganese(IV) oxide; n-butyllithium; boron trifluoride diethyl etherate; hydrogen; diisobutylaluminium hydride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; toluene; benzene; 4: Dess-Martin oxidation;
DOI:10.1021/ol0527678