(3R)-(3S,4S,E)-1-iodo-2,4-dimethylhexa-1,5-dien-3-yl 3-((tert-butyldimethylsilyl)oxy)-5-((4R,5S)-2-(4-methoxyphenyl)-4-methyl-5-vinyl-1,3-dioxolan-4-yl)pentanoate

Base Information

Chemical Name:(3R)-(3S,4S,E)-1-iodo-2,4-dimethylhexa-1,5-dien-3-yl 3-((tert-butyldimethylsilyl)oxy)-5-((4R,5S)-2-(4-methoxyphenyl)-4-methyl-5-vinyl-1,3-dioxolan-4-yl)pentanoate
CAS No.:1403584-91-7
Molecular Formula:C₃₂H₄₉IO₆Si
Molecular Weight:684.727
Hs Code.:

(3R)-(3S,4S,E)-1-iodo-2,4-dimethylhexa-1,5-dien-3-yl 3-((tert-butyldimethylsilyl)oxy)-5-((4R,5S)-2-(4-methoxyphenyl)-4-methyl-5-vinyl-1,3-dioxolan-4-yl)pentanoate

Synonyms:(3R)-(3S,4S,E)-1-iodo-2,4-dimethylhexa-1,5-dien-3-yl 3-((tert-butyldimethylsilyl)oxy)-5-((4R,5S)-2-(4-methoxyphenyl)-4-methyl-5-vinyl-1,3-dioxolan-4-yl)pentanoate

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Chemical Property of (3R)-(3S,4S,E)-1-iodo-2,4-dimethylhexa-1,5-dien-3-yl 3-((tert-butyldimethylsilyl)oxy)-5-((4R,5S)-2-(4-methoxyphenyl)-4-methyl-5-vinyl-1,3-dioxolan-4-yl)pentanoate

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Technology Process of (3R)-(3S,4S,E)-1-iodo-2,4-dimethylhexa-1,5-dien-3-yl 3-((tert-butyldimethylsilyl)oxy)-5-((4R,5S)-2-(4-methoxyphenyl)-4-methyl-5-vinyl-1,3-dioxolan-4-yl)pentanoate

There total 11 articles about (3R)-(3S,4S,E)-1-iodo-2,4-dimethylhexa-1,5-dien-3-yl 3-((tert-butyldimethylsilyl)oxy)-5-((4R,5S)-2-(4-methoxyphenyl)-4-methyl-5-vinyl-1,3-dioxolan-4-yl)pentanoate 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: 80.0%

: (E)-(3S,4S)-1-iodo-2,4-dimethylhexa-1,5-dien-3-ol

: 1403584-90-6
(3R)-3-((tert-butyldimethylsilyl)oxy)-5-((4R,5S)-2-(4-methoxyphenyl)-4-methyl-5-vinyl-1,3-dioxolan-4-yl)pentanoic acid

: 1403584-91-7
(3R)-(3S,4S,E)-1-iodo-2,4-dimethylhexa-1,5-dien-3-yl 3-((tert-butyldimethylsilyl)oxy)-5-((4R,5S)-2-(4-methoxyphenyl)-4-methyl-5-vinyl-1,3-dioxolan-4-yl)pentanoate

Guidance literature:: With dmap; 2,2-dimethylpropanoic anhydride; In neat (no solvent); at 50 ℃; for 5h; Time;

Reference yield:

: 3-((4R,5S)-2-(4-methoxyphenyl)-4-methyl-5-vinyl-1,3-dioxolan-4-yl)propan-1-ol

: 1403584-91-7
(3R)-(3S,4S,E)-1-iodo-2,4-dimethylhexa-1,5-dien-3-yl 3-((tert-butyldimethylsilyl)oxy)-5-((4R,5S)-2-(4-methoxyphenyl)-4-methyl-5-vinyl-1,3-dioxolan-4-yl)pentanoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 0 °C / Inert atmosphere

2.1: phenylborondichloride / dichloromethane / 0.17 h / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

2.3: 7 h / -78 - 20 °C / Inert atmosphere

3.1: 2,6-dimethylpyridine / dichloromethane / 1 h / -78 - 20 °C / Inert atmosphere

4.1: lithium hydroxide; water / tetrahydrofuran; acetonitrile / 0 - 20 °C / Inert atmosphere

5.1: dmap; camphor-10-sulfonic acid; dicyclohexyl-carbodiimide / dichloromethane / 0 - 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; dmap; camphor-10-sulfonic acid; phenylborondichloride; water; sodium hydrogencarbonate; Dess-Martin periodane; dicyclohexyl-carbodiimide; lithium hydroxide; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/ol3023006

Reference yield:

: 1403584-89-3
3-((4R,5S)-2-(4-methoxyphenyl)-4-methyl-5-vinyl-1,3-dioxolan-4-yl)propanal

: 1403584-91-7
(3R)-(3S,4S,E)-1-iodo-2,4-dimethylhexa-1,5-dien-3-yl 3-((tert-butyldimethylsilyl)oxy)-5-((4R,5S)-2-(4-methoxyphenyl)-4-methyl-5-vinyl-1,3-dioxolan-4-yl)pentanoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: phenylborondichloride / dichloromethane / 0.17 h / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

1.3: 7 h / -78 - 20 °C / Inert atmosphere

2.1: 2,6-dimethylpyridine / dichloromethane / 1 h / -78 - 20 °C / Inert atmosphere

3.1: lithium hydroxide; water / tetrahydrofuran; acetonitrile / 0 - 20 °C / Inert atmosphere

4.1: dmap; camphor-10-sulfonic acid; dicyclohexyl-carbodiimide / dichloromethane / 0 - 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; dmap; camphor-10-sulfonic acid; phenylborondichloride; water; dicyclohexyl-carbodiimide; lithium hydroxide; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/ol3023006