(2E,5S,5R,7R,9Z,11S,14E)-7,11-epoxy-5,6-(isopropylidenedioxy)-16-(4-methoxybenzyloxy)-2,6,10,14-tetramethylhexadeca-2,9,14-trien-1-ol

Base Information

Chemical Name:(2E,5S,5R,7R,9Z,11S,14E)-7,11-epoxy-5,6-(isopropylidenedioxy)-16-(4-methoxybenzyloxy)-2,6,10,14-tetramethylhexadeca-2,9,14-trien-1-ol
CAS No.:950598-32-0
Molecular Formula:C₃₁H₄₆O₆
Molecular Weight:514.703
Hs Code.:

Synonyms:(2E,5S,5R,7R,9Z,11S,14E)-7,11-epoxy-5,6-(isopropylidenedioxy)-16-(4-methoxybenzyloxy)-2,6,10,14-tetramethylhexadeca-2,9,14-trien-1-ol

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Chemical Property of (2E,5S,5R,7R,9Z,11S,14E)-7,11-epoxy-5,6-(isopropylidenedioxy)-16-(4-methoxybenzyloxy)-2,6,10,14-tetramethylhexadeca-2,9,14-trien-1-ol

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Technology Process of (2E,5S,5R,7R,9Z,11S,14E)-7,11-epoxy-5,6-(isopropylidenedioxy)-16-(4-methoxybenzyloxy)-2,6,10,14-tetramethylhexadeca-2,9,14-trien-1-ol

There total 23 articles about (2E,5S,5R,7R,9Z,11S,14E)-7,11-epoxy-5,6-(isopropylidenedioxy)-16-(4-methoxybenzyloxy)-2,6,10,14-tetramethylhexadeca-2,9,14-trien-1-ol 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: 91.0%

: 950598-42-2
C₂₈H₄₂O₆

: 77-76-9
2,2-dimethoxy-propane

: 950598-32-0
(2E,5S,5R,7R,9Z,11S,14E)-7,11-epoxy-5,6-(isopropylidenedioxy)-16-(4-methoxybenzyloxy)-2,6,10,14-tetramethylhexadeca-2,9,14-trien-1-ol

Guidance literature:: With pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1021/ja073952e

Reference yield:

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

: 950598-32-0
(2E,5S,5R,7R,9Z,11S,14E)-7,11-epoxy-5,6-(isopropylidenedioxy)-16-(4-methoxybenzyloxy)-2,6,10,14-tetramethylhexadeca-2,9,14-trien-1-ol

Guidance literature:: Multi-step reaction with 15 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

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; lithium diisopropyl amide; 4 A molecular sieve; In methanol; diethyl ether; dichloromethane; toluene; 4: Wittig reaction / 7: Sharpless asymmetric epoxidation / 12: Wittig reaction;
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

: 950598-32-0
(2E,5S,5R,7R,9Z,11S,14E)-7,11-epoxy-5,6-(isopropylidenedioxy)-16-(4-methoxybenzyloxy)-2,6,10,14-tetramethylhexadeca-2,9,14-trien-1-ol

Guidance literature:: Multi-step reaction with 16 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

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