{(2R,4R,6S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-4-yl}-acetonitrile

Base Information

Chemical Name:{(2R,4R,6S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-4-yl}-acetonitrile
CAS No.:197771-11-2
Molecular Formula:C₂₂H₃₅NO₂SSi
Molecular Weight:405.677
Hs Code.:

Synonyms:{(2R,4R,6S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-4-yl}-acetonitrile

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of {(2R,4R,6S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-4-yl}-acetonitrile

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of {(2R,4R,6S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-4-yl}-acetonitrile

There total 15 articles about {(2R,4R,6S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-4-yl}-acetonitrile 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: 80.0%

: 108-98-5
thiophenol

: 197771-09-8
{(2R,4R)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-ethoxy-tetrahydro-pyran-4-yl}-acetonitrile

: 197771-11-2
{(2R,4R,6S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-4-yl}-acetonitrile

Guidance literature:: With magnesium bromide; In diethyl ether;
DOI:10.1016/S0040-4039(97)01780-2

Reference yield: 48.0%

: 108-98-5
thiophenol

: 477200-73-0
{(R)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-ethoxy-tetrahydro-pyran-4-yl}-acetonitrile

: 197771-11-2
{(2R,4R,6S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-4-yl}-acetonitrile

: {(2R,4S,6S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-4-yl}-acetonitrile

Guidance literature:: With magnesium bromide; In diethyl ether; at 20 ℃; for 1h;
DOI:10.1021/jo020537q

Reference yield:

: 112897-05-9
(5R,4R)-6-tert-butyldimethylsilyloxy-4-hydroxy-5-methylhex-1-ene

: 197771-11-2
{(2R,4R,6S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-6-phenylsulfanyl-tetrahydro-pyran-4-yl}-acetonitrile

Guidance literature:: Multi-step reaction with 5 steps

1: 92 percent / N-iodosuccinimide / CH₂Cl₂ / 15 h / -23 - 0 °C

2: 97 percent / OsO₄; sodium periodate / tetrahydrofuran; H₂O; propan-2-ol / 15 h

3: 2.44 g / toluene / 12 h / 70 °C

4: tri-n-butylstannane; azobisisobutyronitrile / toluene / 2 h / 80 °C

5: 48 percent / MgBr₂*OEt₂ / diethyl ether / 1 h / 20 °C

With sodium periodate; N-iodo-succinimide; osmium(VIII) oxide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; magnesium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; water; isopropyl alcohol; toluene; 3: Wittig reaction;
DOI:10.1021/jo020537q