(2E,4E)-(R)-6-((2R,4R,6S)-4-Cyanomethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl)-2-methyl-hepta-2,4-dienoic acid methyl ester

Base Information

Chemical Name:(2E,4E)-(R)-6-((2R,4R,6S)-4-Cyanomethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl)-2-methyl-hepta-2,4-dienoic acid methyl ester
CAS No.:197771-13-4
Molecular Formula:C₂₂H₂₇NO₃S
Molecular Weight:385.527
Hs Code.:

Synonyms:(2E,4E)-(R)-6-((2R,4R,6S)-4-Cyanomethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl)-2-methyl-hepta-2,4-dienoic acid methyl ester

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Chemical Property of (2E,4E)-(R)-6-((2R,4R,6S)-4-Cyanomethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl)-2-methyl-hepta-2,4-dienoic acid methyl ester

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Technology Process of (2E,4E)-(R)-6-((2R,4R,6S)-4-Cyanomethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl)-2-methyl-hepta-2,4-dienoic acid methyl ester

There total 12 articles about (2E,4E)-(R)-6-((2R,4R,6S)-4-Cyanomethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl)-2-methyl-hepta-2,4-dienoic acid methyl ester 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: 88.0%

: 129144-90-7
2-methyl-4-(triphenyl-λ⁵-phosphoranylidene)but-2-enoic acid methyl ester

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

: 197771-13-4
(2E,4E)-(R)-6-((2R,4R,6S)-4-Cyanomethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl)-2-methyl-hepta-2,4-dienoic acid methyl ester

Guidance literature:: In dichloromethane; benzene;
DOI:10.1016/S0040-4039(97)01780-2

Reference yield:

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

: 197771-13-4
(2E,4E)-(R)-6-((2R,4R,6S)-4-Cyanomethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl)-2-methyl-hepta-2,4-dienoic acid methyl ester

Guidance literature:: Multi-step reaction with 12 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

12: 88 percent / benzene; CH₂Cl₂

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; benzene;
DOI:10.1016/S0040-4039(97)01780-2

Reference yield:

: 197771-01-0
(5R,4R)-6-benzyloxy-5-methyl-4-(4-nitrobenzoyloxy)hex-1-ene

: 197771-13-4
(2E,4E)-(R)-6-((2R,4R,6S)-4-Cyanomethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl)-2-methyl-hepta-2,4-dienoic acid methyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 91 percent / BCl₃ / toluene

2: 91 percent / Et₃N, DMAP / CH₂Cl₂

3: 86 percent / NaOH / methanol

4: 79 percent / NIS / CH₂Cl₂ / -20 °C

5: OsO₄, NaIO₄ / tetrahydrofuran; H₂O

6: toluene / 80 °C

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

8: 80 percent / MgBr₂*OEt₂ / diethyl ether

9: 97 percent / HF / acetonitrile; H₂O

10: 71 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 °C

11: 88 percent / benzene; CH₂Cl₂

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; magnesium bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; acetonitrile; benzene;
DOI:10.1016/S0040-4039(97)01780-2