[(2R,4R,6S)-2-((R)-2-Hydroxy-1-methyl-ethyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl]-acetonitrile

Base Information

Chemical Name:[(2R,4R,6S)-2-((R)-2-Hydroxy-1-methyl-ethyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl]-acetonitrile
CAS No.:197771-16-7
Molecular Formula:C₁₆H₂₁NO₂S
Molecular Weight:291.414
Hs Code.:

Synonyms:[(2R,4R,6S)-2-((R)-2-Hydroxy-1-methyl-ethyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl]-acetonitrile

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Chemical Property of [(2R,4R,6S)-2-((R)-2-Hydroxy-1-methyl-ethyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl]-acetonitrile

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Technology Process of [(2R,4R,6S)-2-((R)-2-Hydroxy-1-methyl-ethyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl]-acetonitrile

There total 10 articles about [(2R,4R,6S)-2-((R)-2-Hydroxy-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: 97.0%

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

: 197771-16-7
[(2R,4R,6S)-2-((R)-2-Hydroxy-1-methyl-ethyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl]-acetonitrile

Guidance literature:: With hydrogen fluoride; In water; acetonitrile;
DOI:10.1016/S0040-4039(97)01780-2

Reference yield:

: 94233-74-6
(2R,3S)-1-(benzyloxy)-2-methylhex-5-en-3-ol

: 197771-16-7
[(2R,4R,6S)-2-((R)-2-Hydroxy-1-methyl-ethyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl]-acetonitrile

Guidance literature:: Multi-step reaction with 10 steps

1: 65 percent / DEAD, Ph₃P / tetrahydrofuran

2: 91 percent / BCl₃ / toluene

3: 91 percent / Et₃N, DMAP / CH₂Cl₂

4: 86 percent / NaOH / methanol

5: 79 percent / NIS / CH₂Cl₂ / -20 °C

6: OsO₄, NaIO₄ / tetrahydrofuran; H₂O

7: toluene / 80 °C

8: Bu₃SnH, AIBN / toluene / 80 °C / Irradiation

9: 80 percent / MgBr₂*OEt₂ / diethyl ether

10: 97 percent / HF / acetonitrile; H₂O

With dmap; sodium hydroxide; sodium periodate; N-iodo-succinimide; osmium(VIII) oxide; 2,2'-azobis(isobutyronitrile); hydrogen fluoride; tri-n-butyl-tin hydride; boron trichloride; triethylamine; triphenylphosphine; magnesium bromide; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; acetonitrile;
DOI:10.1016/S0040-4039(97)01780-2

Reference yield:

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

: 197771-16-7
[(2R,4R,6S)-2-((R)-2-Hydroxy-1-methyl-ethyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl]-acetonitrile

Guidance literature:: Multi-step reaction with 6 steps

1: 79 percent / NIS / CH₂Cl₂ / -20 °C

2: OsO₄, NaIO₄ / tetrahydrofuran; H₂O

3: toluene / 80 °C

4: Bu₃SnH, AIBN / toluene / 80 °C / Irradiation

5: 80 percent / MgBr₂*OEt₂ / diethyl ether

6: 97 percent / HF / acetonitrile; H₂O

With sodium periodate; N-iodo-succinimide; osmium(VIII) oxide; 2,2'-azobis(isobutyronitrile); hydrogen fluoride; tri-n-butyl-tin hydride; magnesium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; water; toluene; acetonitrile;
DOI:10.1016/S0040-4039(97)01780-2