(3S,5R)-3,5-dimethyl-5-[(2R,3E,6S,7E)-2,6-dimethyl-8-phenyl-octa-3,7-dienyl]-1,2-dioxolane-3-acetic acid methyl ester

Base Information

Chemical Name:(3S,5R)-3,5-dimethyl-5-[(2R,3E,6S,7E)-2,6-dimethyl-8-phenyl-octa-3,7-dienyl]-1,2-dioxolane-3-acetic acid methyl ester
CAS No.:883994-36-3
Molecular Formula:C₂₄H₃₄O₄
Molecular Weight:386.532
Hs Code.:

Synonyms:(3S,5R)-3,5-dimethyl-5-[(2R,3E,6S,7E)-2,6-dimethyl-8-phenyl-octa-3,7-dienyl]-1,2-dioxolane-3-acetic acid methyl ester

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Chemical Property of (3S,5R)-3,5-dimethyl-5-[(2R,3E,6S,7E)-2,6-dimethyl-8-phenyl-octa-3,7-dienyl]-1,2-dioxolane-3-acetic acid methyl ester

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Technology Process of (3S,5R)-3,5-dimethyl-5-[(2R,3E,6S,7E)-2,6-dimethyl-8-phenyl-octa-3,7-dienyl]-1,2-dioxolane-3-acetic acid methyl ester

There total 12 articles about (3S,5R)-3,5-dimethyl-5-[(2R,3E,6S,7E)-2,6-dimethyl-8-phenyl-octa-3,7-dienyl]-1,2-dioxolane-3-acetic 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:

: 883898-38-2
(2S,3R)-3-((3E,7E)-(2R,6S)-2,6-Dimethyl-8-phenyl-octa-3,7-dienyl)-3-methyl-oxirane-2-carbaldehyde

: 883994-36-3
(3S,5R)-3,5-dimethyl-5-[(2R,3E,6S,7E)-2,6-dimethyl-8-phenyl-octa-3,7-dienyl]-1,2-dioxolane-3-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 71 percent / tetrahydrofuran; diethyl ether / -78 - 20 °C

2.1: 97 percent / Red-Al / tetrahydrofuran; toluene / 0 °C

3.1: t-BuOK; toluenesulfonyl chloride / tetrahydrofuran / 0 - 20 °C

3.2: 72 percent / NaH / tetrahydrofuran; various solvent(s)

4.1: hydrogen peroxide; Yb(OTf)3 / diethyl ether

5.1: LiN(TMS)2 / tetrahydrofuran / 0.5 h / 0 °C

6.1: 74 percent / pyridine; Dess-Martin periodinane / CH₂Cl₂ / 0 °C

7.1: 77 percent / HF / H₂O / 48 h

8.1: 82 percent / TiCl₄ / CH₂Cl₂ / -78 °C

9.1: sodium methoxide

With pyridine; hydrogen fluoride; potassium tert-butylate; dihydrogen peroxide; sodium methylate; titanium tetrachloride; Dess-Martin periodane; p-toluenesulfonyl chloride; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium hexamethyldisilazane; ytterbium(III) triflate; In tetrahydrofuran; diethyl ether; dichloromethane; water; toluene;
DOI:10.1021/jo0522254

Reference yield:

: 883898-14-4
(2R,3R,5R,6E,9S,10E)-2,3-epoxy-3,5,9-trimethyl-11-phenylundeca-6,10-dien-1-ol

: 883994-36-3
(3S,5R)-3,5-dimethyl-5-[(2R,3E,6S,7E)-2,6-dimethyl-8-phenyl-octa-3,7-dienyl]-1,2-dioxolane-3-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: pyridine; Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 °C

2.1: 71 percent / tetrahydrofuran; diethyl ether / -78 - 20 °C

3.1: 97 percent / Red-Al / tetrahydrofuran; toluene / 0 °C

4.1: t-BuOK; toluenesulfonyl chloride / tetrahydrofuran / 0 - 20 °C

4.2: 72 percent / NaH / tetrahydrofuran; various solvent(s)

5.1: hydrogen peroxide; Yb(OTf)3 / diethyl ether

6.1: LiN(TMS)2 / tetrahydrofuran / 0.5 h / 0 °C

7.1: 74 percent / pyridine; Dess-Martin periodinane / CH₂Cl₂ / 0 °C

8.1: 77 percent / HF / H₂O / 48 h

9.1: 82 percent / TiCl₄ / CH₂Cl₂ / -78 °C

10.1: sodium methoxide

With pyridine; hydrogen fluoride; potassium tert-butylate; dihydrogen peroxide; sodium methylate; titanium tetrachloride; Dess-Martin periodane; p-toluenesulfonyl chloride; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium hexamethyldisilazane; ytterbium(III) triflate; In tetrahydrofuran; diethyl ether; dichloromethane; water; toluene;
DOI:10.1021/jo0522254

Reference yield:

: 883898-18-8
(2R,4R)-2-[(2R,3E,6S,7E)-2,6-dimethyl-8-phenylocta-3,7-dienyl]-2,4-dimethyloxetane

: 883994-36-3
(3S,5R)-3,5-dimethyl-5-[(2R,3E,6S,7E)-2,6-dimethyl-8-phenyl-octa-3,7-dienyl]-1,2-dioxolane-3-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: hydrogen peroxide; Yb(OTf)3 / diethyl ether

2: LiN(TMS)2 / tetrahydrofuran / 0.5 h / 0 °C

3: 74 percent / pyridine; Dess-Martin periodinane / CH₂Cl₂ / 0 °C

4: 77 percent / HF / H₂O / 48 h

5: 82 percent / TiCl₄ / CH₂Cl₂ / -78 °C

6: sodium methoxide

With pyridine; hydrogen fluoride; dihydrogen peroxide; sodium methylate; titanium tetrachloride; Dess-Martin periodane; lithium hexamethyldisilazane; ytterbium(III) triflate; In tetrahydrofuran; diethyl ether; dichloromethane; water;
DOI:10.1021/jo0522254