(E)-(5S,6R)-6-benzyloxymethoxy-5,7-dimethyloct-2-enoic acid 1-methylcyclopentyl ester

Base Information

Chemical Name:(E)-(5S,6R)-6-benzyloxymethoxy-5,7-dimethyloct-2-enoic acid 1-methylcyclopentyl ester
CAS No.:1026340-90-8
Molecular Formula:C₂₄H₃₆O₄
Molecular Weight:388.547
Hs Code.:

Synonyms:(E)-(5S,6R)-6-benzyloxymethoxy-5,7-dimethyloct-2-enoic acid 1-methylcyclopentyl ester

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Chemical Property of (E)-(5S,6R)-6-benzyloxymethoxy-5,7-dimethyloct-2-enoic acid 1-methylcyclopentyl ester

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Technology Process of (E)-(5S,6R)-6-benzyloxymethoxy-5,7-dimethyloct-2-enoic acid 1-methylcyclopentyl ester

There total 9 articles about (E)-(5S,6R)-6-benzyloxymethoxy-5,7-dimethyloct-2-enoic acid 1-methylcyclopentyl ester 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: 81.0%

: 906534-76-7
(3S,4R)-4-Benzyloxymethoxy-3,5-dimethyl-hexanal

: (triphenyl-λ⁵-phosphanylidene)-acetic acid 1-methyl-cyclopentyl ester

: 1026340-90-8
(E)-(5S,6R)-6-benzyloxymethoxy-5,7-dimethyloct-2-enoic acid 1-methylcyclopentyl ester

Guidance literature:: In dichloromethane; at 20 ℃; for 18h;
DOI:10.1021/jo061098o

Reference yield:

: 906534-75-6
(3S,4R)-4-benzyloxymethoxy-3,5-dimethylhexan-1-ol

: 1026340-90-8
(E)-(5S,6R)-6-benzyloxymethoxy-5,7-dimethyloct-2-enoic acid 1-methylcyclopentyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 81 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2: 81 percent / CH₂Cl₂ / 18 h / 20 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; 1: Swern oxidation / 2: Wittig olefination;
DOI:10.1021/jo061098o

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 1026340-90-8
(E)-(5S,6R)-6-benzyloxymethoxy-5,7-dimethyloct-2-enoic acid 1-methylcyclopentyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 85 percent / iPr₂NEt / CH₂Cl₂

2.1: 92 percent / DIBAL-H / CH₂Cl₂ / 4 h / -78 °C

3.1: 97 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

4.1: 91 percent / CH₂Cl₂ / 18 h / 20 °C

5.1: CuI; LiBr / tetrahydrofuran / 0.33 h / -15 °C

5.2: 96 percent / TMSCl / tetrahydrofuran / 3 h / -78 °C

6.1: 93 percent / DIBAL-H / CH₂Cl₂ / 4 h / -78 °C

7.1: 81 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

8.1: 81 percent / CH₂Cl₂ / 18 h / 20 °C

With copper(l) iodide; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium bromide; In tetrahydrofuran; dichloromethane; 3.1: Swern oxidation / 4.1: Wittig olefination / 7.1: Swern oxidation / 8.1: Wittig olefination;
DOI:10.1021/jo061098o