(2R,3S,6R,8S)-2-{3-[(tert-butyldiphenyl)oxy]propyl}-3-methyl-8-[(E)-2-phenylethenyl]-1,7-dioxaspiro[5.5]undecane

Base Information

Chemical Name:(2R,3S,6R,8S)-2-{3-[(tert-butyldiphenyl)oxy]propyl}-3-methyl-8-[(E)-2-phenylethenyl]-1,7-dioxaspiro[5.5]undecane
CAS No.:1340479-65-3
Molecular Formula:C₃₇H₄₈O₃Si
Molecular Weight:568.872
Hs Code.:

Synonyms:(2R,3S,6R,8S)-2-{3-[(tert-butyldiphenyl)oxy]propyl}-3-methyl-8-[(E)-2-phenylethenyl]-1,7-dioxaspiro[5.5]undecane

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Chemical Property of (2R,3S,6R,8S)-2-{3-[(tert-butyldiphenyl)oxy]propyl}-3-methyl-8-[(E)-2-phenylethenyl]-1,7-dioxaspiro[5.5]undecane

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Technology Process of (2R,3S,6R,8S)-2-{3-[(tert-butyldiphenyl)oxy]propyl}-3-methyl-8-[(E)-2-phenylethenyl]-1,7-dioxaspiro[5.5]undecane

There total 13 articles about (2R,3S,6R,8S)-2-{3-[(tert-butyldiphenyl)oxy]propyl}-3-methyl-8-[(E)-2-phenylethenyl]-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: 59.0%

: 1340479-64-2
(3E)-7-{(5S)-2-hydroxy-{3-[(tert-butyldiphenyl)oxy]propyl}-5-methyltetrahydro-2H-pyran-2-yl}hept-3-en-2-yl acetate

: 1340479-75-5
(2R,3S)-2-{3-[(tert-butyldiphenyl)oxy]propyl}-3-methyl-5-[(E)-2-phenylethenyl]-3,4,5,6,7,8-hexahydro-2H-chromene

: 1340479-65-3
(2R,3S,6R,8S)-2-{3-[(tert-butyldiphenyl)oxy]propyl}-3-methyl-8-[(E)-2-phenylethenyl]-1,7-dioxaspiro[5.5]undecane

Guidance literature:: With iron (III) chloride hexahydrate; In dichloromethane; water; at 20 ℃; for 4.5h; Inert atmosphere;
DOI:10.1021/ol202483u

Reference yield:

: 1340479-62-0
(5S,6R)-6-{3-[(tert-butyldiphenyl)oxy]propyl}-5-methyltetrahydro-2H-pyran-2-one

: 1340479-75-5
(2R,3S)-2-{3-[(tert-butyldiphenyl)oxy]propyl}-3-methyl-5-[(E)-2-phenylethenyl]-3,4,5,6,7,8-hexahydro-2H-chromene

: 1340479-65-3
(2R,3S,6R,8S)-2-{3-[(tert-butyldiphenyl)oxy]propyl}-3-methyl-8-[(E)-2-phenylethenyl]-1,7-dioxaspiro[5.5]undecane

Guidance literature:: Multi-step reaction with 3 steps

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

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

2.2: 2 h / 20 °C / Inert atmosphere; Microwave irradiation

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

With Hoveyda-Grubbs catalyst second generation; iron (III) chloride hexahydrate; In diethyl ether; dichloromethane; cyclohexane; water;
DOI:10.1021/ol202483u

Reference yield:

: 130372-07-5
4-(tret-butyldiphenylsilyloxy)butan-1-ol

: 1340479-75-5
(2R,3S)-2-{3-[(tert-butyldiphenyl)oxy]propyl}-3-methyl-5-[(E)-2-phenylethenyl]-3,4,5,6,7,8-hexahydro-2H-chromene

: 1340479-65-3
(2R,3S,6R,8S)-2-{3-[(tert-butyldiphenyl)oxy]propyl}-3-methyl-8-[(E)-2-phenylethenyl]-1,7-dioxaspiro[5.5]undecane

Guidance literature:: Multi-step reaction with 8 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

1.2: 0.67 h / -78 °C / Inert atmosphere

2.1: C₄₀H₄₀O₄Ti / tetrahydrofuran; diethyl ether / 2.17 h / -78 - 0 °C / Inert atmosphere

2.2: 20 h / -78 - 20 °C / Inert atmosphere

2.3: 48 h / 20 °C / Inert atmosphere

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

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

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

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

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

7.2: 2 h / 20 °C / Inert atmosphere; Microwave irradiation

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

With Hoveyda-Grubbs catalyst second generation; oxalyl dichloride; iron (III) chloride hexahydrate; C₄₀H₄₀O₄Ti; palladium 10% on activated carbon; camphor-10-sulfonic acid; hydrogen; dimethyl sulfoxide; In tetrahydrofuran; diethyl ether; dichloromethane; cyclohexane; water; ethyl acetate;
DOI:10.1021/ol202483u