(R,Z)-((3R,4S)-1-(tert-butyldiphenylsilyloxy)-4-(4-methoxy-benzyloxy)hex-5-en-3-yl) 8-(4-methoxybenzyloxy)deca-5,9-dienoate

Base Information

Chemical Name:(R,Z)-((3R,4S)-1-(tert-butyldiphenylsilyloxy)-4-(4-methoxy-benzyloxy)hex-5-en-3-yl) 8-(4-methoxybenzyloxy)deca-5,9-dienoate
CAS No.:1384463-69-7
Molecular Formula:C₄₈H₆₀O₇Si
Molecular Weight:777.086
Hs Code.:

Synonyms:(R,Z)-((3R,4S)-1-(tert-butyldiphenylsilyloxy)-4-(4-methoxy-benzyloxy)hex-5-en-3-yl) 8-(4-methoxybenzyloxy)deca-5,9-dienoate

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Chemical Property of (R,Z)-((3R,4S)-1-(tert-butyldiphenylsilyloxy)-4-(4-methoxy-benzyloxy)hex-5-en-3-yl) 8-(4-methoxybenzyloxy)deca-5,9-dienoate

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Technology Process of (R,Z)-((3R,4S)-1-(tert-butyldiphenylsilyloxy)-4-(4-methoxy-benzyloxy)hex-5-en-3-yl) 8-(4-methoxybenzyloxy)deca-5,9-dienoate

There total 14 articles about (R,Z)-((3R,4S)-1-(tert-butyldiphenylsilyloxy)-4-(4-methoxy-benzyloxy)hex-5-en-3-yl) 8-(4-methoxybenzyloxy)deca-5,9-dienoate 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: 92.0%

: 1330680-40-4
(8R,5Z)-8-(4-methoxybenzyloxy)deca-5,9-dienoic acid

: 1384463-70-0
(3R,4S)-1-(tert-butyldiphenylsilyloxy)-4-(4-methoxy-benzyl-oxy)hex-5-en-3-ol

: 1384463-69-7
(R,Z)-((3R,4S)-1-(tert-butyldiphenylsilyloxy)-4-(4-methoxy-benzyloxy)hex-5-en-3-yl) 8-(4-methoxybenzyloxy)deca-5,9-dienoate

Guidance literature:: (8R,5Z)-8-(4-methoxybenzyloxy)deca-5,9-dienoic acid; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In toluene; at 0 - 20 ℃; for 0.75h; Inert atmosphere;

(3R,4S)-1-(tert-butyldiphenylsilyloxy)-4-(4-methoxy-benzyl-oxy)hex-5-en-3-ol; With dmap; In toluene; at 0 - 20 ℃; for 6h; Inert atmosphere;
DOI:10.1016/j.tetasy.2012.04.019

Reference yield:

: 1330680-42-6
(R)-9-(tert-butyldimethylsilyloxy)-1-chloronon-4-yn-2-ol

: 1384463-69-7
(R,Z)-((3R,4S)-1-(tert-butyldiphenylsilyloxy)-4-(4-methoxy-benzyloxy)hex-5-en-3-yl) 8-(4-methoxybenzyloxy)deca-5,9-dienoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: sodium hydride / tetrahydrofuran / -78 °C / Inert atmosphere

2.1: quinoline; hydrogen / 2 h / 20 °C

3.1: n-butyllithium / tetrahydrofuran / 2 h / -10 °C / Inert atmosphere

4.1: sodium hydride / tetrahydrofuran / 4 h / Inert atmosphere

5.1: methanol; toluene-4-sulfonic acid / 1 h / 0 - 20 °C / Inert atmosphere

6.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 0.5 h / Inert atmosphere

7.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene; water / tert-butyl alcohol / 2 h / Inert atmosphere

8.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 0.75 h / 0 - 20 °C / Inert atmosphere

8.2: 6 h / 0 - 20 °C / Inert atmosphere

With quinoline; methanol; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; 2,4,6-trichlorobenzoyl chloride; water; hydrogen; sodium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; dichloromethane; toluene; tert-butyl alcohol; 7.1: Pinnick reaction;
DOI:10.1016/j.tetasy.2012.04.019

Reference yield:

: 1384463-72-2
(R)-3-(tert-butyldiphenylsilyloxy)-1-((S)-oxiran-2-yl) propan-1-ol

: 1384463-69-7
(R,Z)-((3R,4S)-1-(tert-butyldiphenylsilyloxy)-4-(4-methoxy-benzyloxy)hex-5-en-3-yl) 8-(4-methoxybenzyloxy)deca-5,9-dienoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -20 °C / Inert atmosphere

1.2: 3 h / -20 - 20 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.75 h / 0 - 20 °C / Inert atmosphere

2.2: 4 h / 0 - 20 °C / Inert atmosphere

3.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 0.75 h / 0 - 20 °C / Inert atmosphere

3.2: 6 h / 0 - 20 °C / Inert atmosphere

With n-butyllithium; 2,4,6-trichlorobenzoyl chloride; sodium hydride; triethylamine; In tetrahydrofuran; hexane; toluene; mineral oil;
DOI:10.1016/j.tetasy.2012.04.019