(4R,7R,E)-((2R,3S)-3-(benzyloxy)pent-4-en-2-yl) 7-(tertbutyldimethylsilyloxy)-4-(4-methoxybenzyloxy)oct-2-enoate

Base Information

Chemical Name:(4R,7R,E)-((2R,3S)-3-(benzyloxy)pent-4-en-2-yl) 7-(tertbutyldimethylsilyloxy)-4-(4-methoxybenzyloxy)oct-2-enoate
CAS No.:1369492-90-9
Molecular Formula:C₃₄H₅₀O₆Si
Molecular Weight:582.853
Hs Code.:

Synonyms:(4R,7R,E)-((2R,3S)-3-(benzyloxy)pent-4-en-2-yl) 7-(tertbutyldimethylsilyloxy)-4-(4-methoxybenzyloxy)oct-2-enoate

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Chemical Property of (4R,7R,E)-((2R,3S)-3-(benzyloxy)pent-4-en-2-yl) 7-(tertbutyldimethylsilyloxy)-4-(4-methoxybenzyloxy)oct-2-enoate

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Technology Process of (4R,7R,E)-((2R,3S)-3-(benzyloxy)pent-4-en-2-yl) 7-(tertbutyldimethylsilyloxy)-4-(4-methoxybenzyloxy)oct-2-enoate

There total 10 articles about (4R,7R,E)-((2R,3S)-3-(benzyloxy)pent-4-en-2-yl) 7-(tertbutyldimethylsilyloxy)-4-(4-methoxybenzyloxy)oct-2-enoate 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:

: 79414-02-1,121785-58-8,121785-61-3,133522-08-4,133522-10-8,133522-11-9,133522-09-5
methyl (-)-(5R,2E)-5-(tert-butyldimethylsilyloxy)hexenoate

: 1369492-90-9
(4R,7R,E)-((2R,3S)-3-(benzyloxy)pent-4-en-2-yl) 7-(tertbutyldimethylsilyloxy)-4-(4-methoxybenzyloxy)oct-2-enoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: sodium tetrahydroborate; nickel(II) chloride hexahydrate / methanol / 1 h / 0 - 20 °C

2.1: diisobutylaluminium hydride / dichloromethane / 0.5 h / -78 °C

2.2: 0.5 h / Saturated solution

3.1: L-proline / dimethyl sulfoxide / 20 °C / Inert atmosphere

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / dimethyl sulfoxide; acetonitrile / 1 h / 0 - 20 °C / Inert atmosphere

5.1: copper(ll) sulfate pentahydrate / methanol / 20 °C

6.1: toluene-4-sulfonic acid / dichloromethane / 8 h / 0 - 20 °C

7.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 8 h / 20 °C

8.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 12 h / 0 °C

With dmap; sodium tetrahydroborate; copper(ll) sulfate pentahydrate; nickel(II) chloride hexahydrate; lithium hydroxide monohydrate; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; L-proline; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; acetonitrile; 4.1: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.tetasy.2012.01.014

Reference yield:

: 110236-74-3
(2R,3S)-3-(benzyloxy)pent-4-en-2-yloxy tert-butyldimethylsilane

: 1369492-90-9
(4R,7R,E)-((2R,3S)-3-(benzyloxy)pent-4-en-2-yl) 7-(tertbutyldimethylsilyloxy)-4-(4-methoxybenzyloxy)oct-2-enoate

Guidance literature:: Multi-step reaction with 2 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 8 h / 0 - 20 °C

2: dmap; dicyclohexyl-carbodiimide / dichloromethane / 12 h / 0 °C

With dmap; tetrabutyl ammonium fluoride; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tetasy.2012.01.014

Reference yield:

: 1369492-87-4
ethyl (2E,4R,7R)-7-{[(tert-butyl)(dimethyl)silyl]oxy}-4-hydroxyoct-2-enoate

: 1369492-90-9
(4R,7R,E)-((2R,3S)-3-(benzyloxy)pent-4-en-2-yl) 7-(tertbutyldimethylsilyloxy)-4-(4-methoxybenzyloxy)oct-2-enoate

Guidance literature:: Multi-step reaction with 3 steps

1: toluene-4-sulfonic acid / dichloromethane / 8 h / 0 - 20 °C

2: lithium hydroxide monohydrate / tetrahydrofuran; water / 8 h / 20 °C

3: dmap; dicyclohexyl-carbodiimide / dichloromethane / 12 h / 0 °C

With dmap; lithium hydroxide monohydrate; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/j.tetasy.2012.01.014