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

Base Information

Chemical Name:[(2R,4R,6S)-2-((S)-1-Methyl-2-oxo-ethyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl]-acetonitrile
CAS No.:197771-12-3
Molecular Formula:C₁₆H₁₉NO₂S
Molecular Weight:289.398
Hs Code.:

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

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

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

There total 11 articles about [(2R,4R,6S)-2-((S)-1-Methyl-2-oxo-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: 71.0%

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

: 197771-12-3
[(2R,4R,6S)-2-((S)-1-Methyl-2-oxo-ethyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl]-acetonitrile

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃;
DOI:10.1016/S0040-4039(97)01780-2

Reference yield:

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

: 197771-12-3
[(2R,4R,6S)-2-((S)-1-Methyl-2-oxo-ethyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl]-acetonitrile

Guidance literature:: Multi-step reaction with 11 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

11: 71 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 °C

With dmap; sodium hydroxide; sodium periodate; N-iodo-succinimide; osmium(VIII) oxide; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); hydrogen fluoride; tri-n-butyl-tin hydride; boron trichloride; dimethyl sulfoxide; 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

: 197771-12-3
[(2R,4R,6S)-2-((S)-1-Methyl-2-oxo-ethyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl]-acetonitrile

Guidance literature:: Multi-step reaction with 7 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

7: 71 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 °C

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