(2R,3S,6R,8S)-8-[(1Z,3S)-4-benzyloxy-3-methylbut-1-en-1-yl]-2-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]-3-methyl-1,7-dioxaspiro[5.5]undecane

Base Information

• Chemical Name: (2R,3S,6R,8S)-8-[(1Z,3S)-4-benzyloxy-3-methylbut-1-en-1-yl]-2-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]-3-methyl-1,7-dioxaspiro[5.5]undecane
• CAS No.: 1340479-78-8
• Molecular Formula: C₃₃H₄₁NO₅
• Molecular Weight: 531.692

Synonyms:(2R,3S,6R,8S)-8-[(1Z,3S)-4-benzyloxy-3-methylbut-1-en-1-yl]-2-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]-3-methyl-1,7-dioxaspiro[5.5]undecane

Chemical Property of (2R,3S,6R,8S)-8-[(1Z,3S)-4-benzyloxy-3-methylbut-1-en-1-yl]-2-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]-3-methyl-1,7-dioxaspiro[5.5]undecane

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Technology Process of (2R,3S,6R,8S)-8-[(1Z,3S)-4-benzyloxy-3-methylbut-1-en-1-yl]-2-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]-3-methyl-1,7-dioxaspiro[5.5]undecane

There total 17 articles about (2R,3S,6R,8S)-8-[(1Z,3S)-4-benzyloxy-3-methylbut-1-en-1-yl]-2-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]-3-methyl-1,7-dioxaspiro[5.5]undecane 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: 99.0%

phthalimide (136918-14-4,85-41-6) + (2R,3S,6R,8S)-8-[(1Z,3S)-4-benzyloxy-3-methylbut-1-en-1-yl]-2-(3-oxypropyl)-3-methyl-1,7-dioxaspiro[5.5]undecane (1340479-77-7) → (2R,3S,6R,8S)-8-[(1Z,3S)-4-benzyloxy-3-methylbut-1-en-1-yl]-2-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]-3-methyl-1,7-dioxaspiro[5.5]undecane (1340479-78-8)

Guidance literature:

phthalimide; (2R,3S,6R,8S)-8-[(1Z,3S)-4-benzyloxy-3-methylbut-1-en-1-yl]-2-(3-oxypropyl)-3-methyl-1,7-dioxaspiro[5.5]undecane; With triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 3h; Inert atmosphere;

With di-isopropyl azodicarboxylate; In tetrahydrofuran; at 0 ℃; for 2h; Inert atmosphere;

DOI:10.1021/ol202483u

Reference yield:

(R)-3-(benzyloxy-2-methyl-propyl)-triphenyl-phosphonium bromide → (2R,3S,6R,8S)-8-[(1Z,3S)-4-benzyloxy-3-methylbut-1-en-1-yl]-2-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]-3-methyl-1,7-dioxaspiro[5.5]undecane (1340479-78-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 20 °C / Inert atmosphere

1.2: 0.67 h / 0 °C / Inert atmosphere

1.3: 4 h / 0 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 15 °C / Inert atmosphere

3.1: triphenylphosphine / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

3.2: 2 h / 0 °C / Inert atmosphere

With tetrabutyl ammonium fluoride; triphenylphosphine; In tetrahydrofuran; 1.2: Wittig reaction / 3.1: Mitsunobu reaction / 3.2: Mitsunobu reaction;

DOI:10.1021/ol202483u

Reference yield:

(3S,4R)-7-[(tert-butyldiphenyl)oxy]-3-methyl-hept-1-en-4-ol (1269618-58-7) → (2R,3S,6R,8S)-8-[(1Z,3S)-4-benzyloxy-3-methylbut-1-en-1-yl]-2-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]-3-methyl-1,7-dioxaspiro[5.5]undecane (1340479-78-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 2 h / 80 °C / Inert atmosphere; Microwave irradiation

2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 2 h / 20 °C

3.1: camphor-10-sulfonic acid / dichloromethane / 2 h / 20 °C

4.1: diethyl ether; cyclohexane / 16 h / -20 °C / Inert atmosphere

5.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 80 °C / Inert atmosphere; Microwave irradiation

5.2: 2 h / 20 °C / Inert atmosphere; Microwave irradiation

6.1: iron (III) chloride hexahydrate / dichloromethane; water / 4.5 h / 20 °C / Inert atmosphere

7.1: ozone / dichloromethane / -78 °C

7.2: -78 - 20 °C / Inert atmosphere

7.3: 20 °C / Inert atmosphere

8.1: 20 °C / Inert atmosphere

8.2: 0.67 h / 0 °C / Inert atmosphere

8.3: 4 h / 0 °C / Inert atmosphere

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 15 °C / Inert atmosphere

10.1: triphenylphosphine / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

10.2: 2 h / 0 °C / Inert atmosphere

With Hoveyda-Grubbs catalyst second generation; iron (III) chloride hexahydrate; palladium 10% on activated carbon; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; ozone; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; cyclohexane; water; ethyl acetate; 8.2: Wittig reaction / 10.1: Mitsunobu reaction / 10.2: Mitsunobu reaction;

DOI:10.1021/ol202483u

upstream raw materials:

phthalimide

(2R,3S,6R,8S)-8-[(1Z,3S)-4-benzyloxy-3-methylbut-1-en-1-yl]-2-(3-oxypropyl)-3-methyl-1,7-dioxaspiro[5.5]undecane

(3S,4R)-7-[(tert-butyldiphenyl)oxy]-3-methyl-hept-1-en-4-ol

methyl (2E,4S,5R)-5-hydroxy-8-[(tert-butyldiphenyl)oxy]-4-methyl-oct-2-enoate

Downstream raw materials:

2-({3-[(2R,3S,6S,8R)-3-methyl-8-[(3S,4E)-3,5-dimethyl-6-oxohept-4-en-1-yl]-1,7-dioxaspiro[5.5]undec-2-yl]propyl}carbamoyl)benzoic acid

2-({3-[(2R,3S,6S,8R)-3-methyl-8-[(3S,4E,6S)-6-hydroxy-3,5-dimethylhept-4-en-1-yl]-1,7-dioxaspiro[5.5]undec-2-yl]propyl}carbamoyl)benzoic acid

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