(1'R,2S)-5-benzyloxymethyl-2-[1'-(2-methoxyethoxymethoxy)ethyl]-5-hexenoic acid S-ethyl ester

Base Information

Chemical Name:(1'R,2S)-5-benzyloxymethyl-2-[1'-(2-methoxyethoxymethoxy)ethyl]-5-hexenoic acid S-ethyl ester
CAS No.:347886-10-6
Molecular Formula:C₂₂H₃₄O₅S
Molecular Weight:410.575
Hs Code.:

Synonyms:(1'R,2S)-5-benzyloxymethyl-2-[1'-(2-methoxyethoxymethoxy)ethyl]-5-hexenoic acid S-ethyl ester

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Chemical Property of (1'R,2S)-5-benzyloxymethyl-2-[1'-(2-methoxyethoxymethoxy)ethyl]-5-hexenoic acid S-ethyl ester

Chemical Property:

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Technology Process of (1'R,2S)-5-benzyloxymethyl-2-[1'-(2-methoxyethoxymethoxy)ethyl]-5-hexenoic acid S-ethyl ester

There total 8 articles about (1'R,2S)-5-benzyloxymethyl-2-[1'-(2-methoxyethoxymethoxy)ethyl]-5-hexenoic acid S-ethyl 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: 91.0%

: 75-08-1
ethanethiol

: 347886-09-3
(1'R,2S)-5-benzyloxymethyl-2-[1'-(2-methoxyethoxymethoxy)ethyl]-5-hexenoic acid

: 347886-10-6
(1'R,2S)-5-benzyloxymethyl-2-[1'-(2-methoxyethoxymethoxy)ethyl]-5-hexenoic acid S-ethyl ester

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃;
DOI:10.1021/jo026399m

Reference yield:

: 347886-00-4
[2-(bromomethyl)prop-2-en-1-yloxy]methylbenzene

: 347886-10-6
(1'R,2S)-5-benzyloxymethyl-2-[1'-(2-methoxyethoxymethoxy)ethyl]-5-hexenoic acid S-ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: Zn(Cu); N,N-dimethylacetamide / tetrahydrofuran / 3 h / 20 - 60 °C

1.2: 88 percent / CuCN / tetrahydrofuran / 20 °C

2.1: 97 percent / NaOH / methanol / 4 h / 20 °C

3.1: triethylamine / tetrahydrofuran / 1 h / 0 °C

4.1: 13.90 g / 4-(dimethylamino)pyridine; triethylamine / tetrahydrofuran / 120 h / 20 °C

5.1: dibutylboron triflate; triethylamine / CH₂Cl₂ / 0 - 3 °C

5.2: CH₂Cl₂ / -78 - 0 °C

5.3: 67 percent / aqueous hydrogen peroxide / methanol; CH₂Cl₂ / cooling

6.1: 93 percent / diisopropylethylamine / CH₂Cl₂ / 4 h / 20 °C

7.1: 83 percent / aqueous H₂O₂; LiOH*H₂O / tetrahydrofuran / 3 h

8.1: 91 percent / 4-(dimethylamino)pyridine; DCC / CH₂Cl₂ / 0 - 20 °C

With dmap; lithium hydroxide; sodium hydroxide; zinc copper; N,N-dimethyl acetamide; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo026399m

Reference yield:

: 347886-20-8
5-benzyloxymethyl-hex-5-enoic acid

: 347886-10-6
(1'R,2S)-5-benzyloxymethyl-2-[1'-(2-methoxyethoxymethoxy)ethyl]-5-hexenoic acid S-ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: triethylamine / tetrahydrofuran / 1 h / 0 °C

2.1: 13.90 g / 4-(dimethylamino)pyridine; triethylamine / tetrahydrofuran / 120 h / 20 °C

3.1: dibutylboron triflate; triethylamine / CH₂Cl₂ / 0 - 3 °C

3.2: CH₂Cl₂ / -78 - 0 °C

3.3: 67 percent / aqueous hydrogen peroxide / methanol; CH₂Cl₂ / cooling

4.1: 93 percent / diisopropylethylamine / CH₂Cl₂ / 4 h / 20 °C

5.1: 83 percent / aqueous H₂O₂; LiOH*H₂O / tetrahydrofuran / 3 h

6.1: 91 percent / 4-(dimethylamino)pyridine; DCC / CH₂Cl₂ / 0 - 20 °C

With dmap; lithium hydroxide; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo026399m