(2E,6S,7Z,10R,11R,12S,14S)-6,10:14,15-diepoxy-11,12-isopropylidenedioxy-3,7,11,15-tetramethyl-1-(phenylthio)hexadeca-2,7-diene

Base Information

Chemical Name:(2E,6S,7Z,10R,11R,12S,14S)-6,10:14,15-diepoxy-11,12-isopropylidenedioxy-3,7,11,15-tetramethyl-1-(phenylthio)hexadeca-2,7-diene
CAS No.:950598-33-1
Molecular Formula:C₂₉H₄₂O₄S
Molecular Weight:486.716
Hs Code.:

Synonyms:(2E,6S,7Z,10R,11R,12S,14S)-6,10:14,15-diepoxy-11,12-isopropylidenedioxy-3,7,11,15-tetramethyl-1-(phenylthio)hexadeca-2,7-diene

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Chemical Property of (2E,6S,7Z,10R,11R,12S,14S)-6,10:14,15-diepoxy-11,12-isopropylidenedioxy-3,7,11,15-tetramethyl-1-(phenylthio)hexadeca-2,7-diene

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Technology Process of (2E,6S,7Z,10R,11R,12S,14S)-6,10:14,15-diepoxy-11,12-isopropylidenedioxy-3,7,11,15-tetramethyl-1-(phenylthio)hexadeca-2,7-diene

There total 27 articles about (2E,6S,7Z,10R,11R,12S,14S)-6,10:14,15-diepoxy-11,12-isopropylidenedioxy-3,7,11,15-tetramethyl-1-(phenylthio)hexadeca-2,7-diene 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: 89.0%

: 950598-47-7
C₂₃H₃₈O₅

: 882-33-7
diphenyldisulfane

: 950598-33-1
(2E,6S,7Z,10R,11R,12S,14S)-6,10:14,15-diepoxy-11,12-isopropylidenedioxy-3,7,11,15-tetramethyl-1-(phenylthio)hexadeca-2,7-diene

Guidance literature:: With pyridine; tributylphosphine; In dichloromethane; at 20 ℃; for 2.5h;
DOI:10.1021/ja073952e

Reference yield:

: 906624-11-1
(3S,6E)-8-(4-methoxybenzyloxy)-2,6-dimethylocta-1,6-dien-3-ol

: 950598-33-1
(2E,6S,7Z,10R,11R,12S,14S)-6,10:14,15-diepoxy-11,12-isopropylidenedioxy-3,7,11,15-tetramethyl-1-(phenylthio)hexadeca-2,7-diene

Guidance literature:: Multi-step reaction with 20 steps

1: 97 percent / DCC; DMAP / CH₂Cl₂ / 0 °C

2: 74 percent / [RuCl₂(=CHPh)(PCy₃)(SIMes)] / CH₂Cl₂ / 40 °C

3: DIBALH / CH₂Cl₂ / -78 °C

4: toluene / 80 °C

5: imidazole / CH₂Cl₂

6: DIBALH / CH₂Cl₂ / -78 °C

7: L-(+)-diethyl tartrate; Ti(i-PrO)4; TBHP / molecular sieves 4 Angstroem / CH₂Cl₂ / -20 °C

8: SO₃*pyridine; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

9: 63 percent / LDA / diethyl ether / -78 °C

10: imidazole / CH₂Cl₂

11: DIBALH / CH₂Cl₂ / -78 °C

12: toluene / 80 °C

13: DIBALH / CH₂Cl₂ / -78 °C

14: 97 percent / BF₃*OEt₂ / methanol / 3 h / -78 - 0 °C

15: 91 percent / PPTS / CH₂Cl₂ / 1 h / 20 °C

16: 95 percent / L-(+)-diethyl tartrate; Ti(i-PrO)4; TBHP / molecular sieves 4 Angstroem / CH₂Cl₂ / 17 h / -40 °C

17: 93 percent / I₂; PPh₃; imidazole / CH₂Cl₂ / 3 h / 0 °C

18: 73 percent / NaBH₃CN / tetrahydrofuran / 18 h / 50 °C

19: 89 percent / DDQ / CH₂Cl₂; H₂O / 0.5 h / 0 °C

20: 89 percent / pyridine; tri-n-butylphosphine / CH₂Cl₂ / 2.5 h / 20 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; tributylphosphine; boron trifluoride diethyl etherate; iodine; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium cyanoborohydride; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; 4 A molecular sieve; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; 4: Wittig reaction / 7: Sharpless asymmetric epoxidation / 12: Wittig reaction / 16: Sharpless asymmetric epoxidation;
DOI:10.1021/ja073952e

Reference yield:

: 906624-08-6
(2R,3S)-2-Iodomethyl-3-[(E)-5-(4-methoxy-benzyloxy)-3-methyl-pent-3-enyl]-2-methyl-oxirane

: 950598-33-1
(2E,6S,7Z,10R,11R,12S,14S)-6,10:14,15-diepoxy-11,12-isopropylidenedioxy-3,7,11,15-tetramethyl-1-(phenylthio)hexadeca-2,7-diene

Guidance literature:: Multi-step reaction with 21 steps

1: H₂O

2: 97 percent / DCC; DMAP / CH₂Cl₂ / 0 °C

3: 74 percent / [RuCl₂(=CHPh)(PCy₃)(SIMes)] / CH₂Cl₂ / 40 °C

4: DIBALH / CH₂Cl₂ / -78 °C

5: toluene / 80 °C

6: imidazole / CH₂Cl₂

7: DIBALH / CH₂Cl₂ / -78 °C

8: L-(+)-diethyl tartrate; Ti(i-PrO)4; TBHP / molecular sieves 4 Angstroem / CH₂Cl₂ / -20 °C

9: SO₃*pyridine; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

10: 63 percent / LDA / diethyl ether / -78 °C

11: imidazole / CH₂Cl₂

12: DIBALH / CH₂Cl₂ / -78 °C

13: toluene / 80 °C

14: DIBALH / CH₂Cl₂ / -78 °C

15: 97 percent / BF₃*OEt₂ / methanol / 3 h / -78 - 0 °C

16: 91 percent / PPTS / CH₂Cl₂ / 1 h / 20 °C

17: 95 percent / L-(+)-diethyl tartrate; Ti(i-PrO)4; TBHP / molecular sieves 4 Angstroem / CH₂Cl₂ / 17 h / -40 °C

18: 93 percent / I₂; PPh₃; imidazole / CH₂Cl₂ / 3 h / 0 °C

19: 73 percent / NaBH₃CN / tetrahydrofuran / 18 h / 50 °C

20: 89 percent / DDQ / CH₂Cl₂; H₂O / 0.5 h / 0 °C

21: 89 percent / pyridine; tri-n-butylphosphine / CH₂Cl₂ / 2.5 h / 20 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; tributylphosphine; boron trifluoride diethyl etherate; water; iodine; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium cyanoborohydride; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; 4 A molecular sieve; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; 5: Wittig reaction / 8: Sharpless asymmetric epoxidation / 13: Wittig reaction / 17: Sharpless asymmetric epoxidation;
DOI:10.1021/ja073952e