5-{(3E,5E)-2-[(tert-butyldimethylsilyl)oxy]hepta-3,5-dien-1-yl}-4-{[(R)-1-{(2R,3R)-3-[(Z)-hepta-1,6-dien-1-yl]oxiran-2-yl}propan-2-yloxy]carbonyl}-1,3-phenylene diacetate

Base Information

Chemical Name:5-{(3E,5E)-2-[(tert-butyldimethylsilyl)oxy]hepta-3,5-dien-1-yl}-4-{[(R)-1-{(2R,3R)-3-[(Z)-hepta-1,6-dien-1-yl]oxiran-2-yl}propan-2-yloxy]carbonyl}-1,3-phenylene diacetate
CAS No.:1622322-40-0
Molecular Formula:C₃₆H₅₂O₈Si
Molecular Weight:640.89
Hs Code.:

5-{(3E,5E)-2-[(tert-butyldimethylsilyl)oxy]hepta-3,5-dien-1-yl}-4-{[(R)-1-{(2R,3R)-3-[(Z)-hepta-1,6-dien-1-yl]oxiran-2-yl}propan-2-yloxy]carbonyl}-1,3-phenylene diacetate

Synonyms:5-{(3E,5E)-2-[(tert-butyldimethylsilyl)oxy]hepta-3,5-dien-1-yl}-4-{[(R)-1-{(2R,3R)-3-[(Z)-hepta-1,6-dien-1-yl]oxiran-2-yl}propan-2-yloxy]carbonyl}-1,3-phenylene diacetate

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Chemical Property of 5-{(3E,5E)-2-[(tert-butyldimethylsilyl)oxy]hepta-3,5-dien-1-yl}-4-{[(R)-1-{(2R,3R)-3-[(Z)-hepta-1,6-dien-1-yl]oxiran-2-yl}propan-2-yloxy]carbonyl}-1,3-phenylene diacetate

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Technology Process of 5-{(3E,5E)-2-[(tert-butyldimethylsilyl)oxy]hepta-3,5-dien-1-yl}-4-{[(R)-1-{(2R,3R)-3-[(Z)-hepta-1,6-dien-1-yl]oxiran-2-yl}propan-2-yloxy]carbonyl}-1,3-phenylene diacetate

There total 9 articles about 5-{(3E,5E)-2-[(tert-butyldimethylsilyl)oxy]hepta-3,5-dien-1-yl}-4-{[(R)-1-{(2R,3R)-3-[(Z)-hepta-1,6-dien-1-yl]oxiran-2-yl}propan-2-yloxy]carbonyl}-1,3-phenylene diacetate 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: 97.0%

: 1643867-95-1
(R)-1-{(2R,3R)-3-[(Z)-hepta-1,6-dien-1-yl]oxiran-2-yl}propan-2-yl 4-acetoxy-2-{(3E,5E)-2-[(tert-butyldimethylsilyl)oxy]hepta-3,5-dien-1-yl}-6-hydroxybenzoate

: 108-24-7
acetic anhydride

: 1622322-40-0
5-{(3E,5E)-2-[(tert-butyldimethylsilyl)oxy]hepta-3,5-dien-1-yl}-4-{[(R)-1-{(2R,3R)-3-[(Z)-hepta-1,6-dien-1-yl]oxiran-2-yl}propan-2-yloxy]carbonyl}-1,3-phenylene diacetate

Guidance literature:: With dmap; In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;
DOI:10.1002/ejoc.201402205

Reference yield:

: (5-hexen-1-yl)triphenylphosphonium iodide

: 1622322-40-0
5-{(3E,5E)-2-[(tert-butyldimethylsilyl)oxy]hepta-3,5-dien-1-yl}-4-{[(R)-1-{(2R,3R)-3-[(Z)-hepta-1,6-dien-1-yl]oxiran-2-yl}propan-2-yloxy]carbonyl}-1,3-phenylene diacetate

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

2.1: tetrahydrofuran / 2 h / -10 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 25 °C / Inert atmosphere; Molecular sieve

4.1: toluene / 3 h / Inert atmosphere; Reflux

4.2: 16 h / 100 °C / Inert atmosphere; Molecular sieve; Sealed tube

5.1: dmap / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

With dmap; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; In tetrahydrofuran; toluene; 1.1: |Wittig Olefination / 2.1: |Wittig Olefination;
DOI:10.1002/ejoc.201402205

Reference yield:

: 1622322-70-6
6-[(2Z,7E,9E)-6-(tert-butyldimethylsilyloxy)-2-hydroxy-4-oxoundeca-2,7,9-trienyl]-2,2-dimethyl-4H-1,3-dioxin-4-one

: 1622322-40-0
5-{(3E,5E)-2-[(tert-butyldimethylsilyl)oxy]hepta-3,5-dien-1-yl}-4-{[(R)-1-{(2R,3R)-3-[(Z)-hepta-1,6-dien-1-yl]oxiran-2-yl}propan-2-yloxy]carbonyl}-1,3-phenylene diacetate

Guidance literature:: Multi-step reaction with 2 steps

1.1: toluene / 3 h / Inert atmosphere; Reflux

1.2: 16 h / 100 °C / Inert atmosphere; Molecular sieve; Sealed tube

2.1: dmap / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

With dmap; In tetrahydrofuran; toluene;
DOI:10.1002/ejoc.201402205