[(2R,4R,6S)-2-((2E,4E)-(R)-6-Hydroxy-1,5-dimethyl-hexa-2,4-dienyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl]-acetonitrile

Base Information

• Chemical Name: [(2R,4R,6S)-2-((2E,4E)-(R)-6-Hydroxy-1,5-dimethyl-hexa-2,4-dienyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl]-acetonitrile
• CAS No.: 197771-15-6
• Molecular Formula: C₂₁H₂₇NO₂S
• Molecular Weight: 357.517

Synonyms:[(2R,4R,6S)-2-((2E,4E)-(R)-6-Hydroxy-1,5-dimethyl-hexa-2,4-dienyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl]-acetonitrile

Chemical Property of [(2R,4R,6S)-2-((2E,4E)-(R)-6-Hydroxy-1,5-dimethyl-hexa-2,4-dienyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl]-acetonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2R,4R,6S)-2-((2E,4E)-(R)-6-Hydroxy-1,5-dimethyl-hexa-2,4-dienyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl]-acetonitrile

There total 13 articles about [(2R,4R,6S)-2-((2E,4E)-(R)-6-Hydroxy-1,5-dimethyl-hexa-2,4-dienyl)-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: 83.0%

(2E,4E)-(R)-6-((2R,4R,6S)-4-Cyanomethyl-6-phenylsulfanyl-tetrahydro-pyran-2-yl)-2-methyl-hepta-2,4-dienoic acid methyl ester (197771-13-4) → [(2R,4R,6S)-2-((2E,4E)-(R)-6-Hydroxy-1,5-dimethyl-hexa-2,4-dienyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl]-acetonitrile (197771-15-6)

Guidance literature:

With diisobutylaluminium hydride; In diethyl ether; at -78 ℃;

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

Reference yield:

(2R,3S)-1-(benzyloxy)-2-methylhex-5-en-3-ol (94233-74-6) → [(2R,4R,6S)-2-((2E,4E)-(R)-6-Hydroxy-1,5-dimethyl-hexa-2,4-dienyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl]-acetonitrile (197771-15-6)

Guidance literature:

Multi-step reaction with 13 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

13: 83 percent / DIBALH / diethyl ether / -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; diisobutylaluminium hydride; 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:

(5R,4R)-6-benzyloxy-5-methyl-4-(4-nitrobenzoyloxy)hex-1-ene (197771-01-0) → [(2R,4R,6S)-2-((2E,4E)-(R)-6-Hydroxy-1,5-dimethyl-hexa-2,4-dienyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl]-acetonitrile (197771-15-6)

Guidance literature:

Multi-step reaction with 12 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

12: 83 percent / DIBALH / diethyl ether / -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; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; magnesium bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; acetonitrile; benzene;

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

upstream raw materials:

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

(2R,3S)-1-(benzyloxy)-2-methylhex-5-en-3-ol

(5R,4R)-6-tert-butyldimethylsilyloxy-4-hydroxy-5-methylhex-1-ene

(5R,4R)-6-benzyloxy-5-methyl-4-(4-nitrobenzoyloxy)hex-1-ene

Downstream raw materials:

[(2R,4R,6S)-2-((2E,4E)-(R)-1,5-Dimethyl-6-oxo-hexa-2,4-dienyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl]-acetonitrile

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