(4R,7R,E)-7-(tert-butyldimethylsilyloxy)-4-(4-methoxy-benzyloxy)oct-2-enoic acid

Base Information

Chemical Name:(4R,7R,E)-7-(tert-butyldimethylsilyloxy)-4-(4-methoxy-benzyloxy)oct-2-enoic acid
CAS No.:1369492-89-6
Molecular Formula:C₂₂H₃₆O₅Si
Molecular Weight:408.61
Hs Code.:

Synonyms:(4R,7R,E)-7-(tert-butyldimethylsilyloxy)-4-(4-methoxy-benzyloxy)oct-2-enoic acid

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Chemical Property of (4R,7R,E)-7-(tert-butyldimethylsilyloxy)-4-(4-methoxy-benzyloxy)oct-2-enoic acid

Chemical Property:

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Technology Process of (4R,7R,E)-7-(tert-butyldimethylsilyloxy)-4-(4-methoxy-benzyloxy)oct-2-enoic acid

There total 9 articles about (4R,7R,E)-7-(tert-butyldimethylsilyloxy)-4-(4-methoxy-benzyloxy)oct-2-enoic acid 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: 87.0%

: 1369492-88-5
ethyl (4R,7R,E)-7-(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)oct-2-enoate

: 1369492-89-6
(4R,7R,E)-7-(tert-butyldimethylsilyloxy)-4-(4-methoxy-benzyloxy)oct-2-enoic acid

Guidance literature:: ethyl (4R,7R,E)-7-(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)oct-2-enoate; With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 20 ℃; for 8h;

With potassium hydrogensulfate; In water;
DOI:10.1016/j.tetasy.2012.01.014

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

: 1369492-89-6
(4R,7R,E)-7-(tert-butyldimethylsilyloxy)-4-(4-methoxy-benzyloxy)oct-2-enoic acid

Guidance literature:: Multi-step reaction with 7 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

With 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; 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:

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

: 1369492-89-6
(4R,7R,E)-7-(tert-butyldimethylsilyloxy)-4-(4-methoxy-benzyloxy)oct-2-enoic acid

Guidance literature:: Multi-step reaction with 2 steps

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

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

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