(6S,2'R)-6-(methoxymethoxy)-5,5-dimethyl-octa-2,7-diynoic acid 1-(toluene-4-sulfonyloxymethyl)-but-2-ynyl ester

Base Information

Chemical Name:(6S,2'R)-6-(methoxymethoxy)-5,5-dimethyl-octa-2,7-diynoic acid 1-(toluene-4-sulfonyloxymethyl)-but-2-ynyl ester
CAS No.:1257866-18-4
Molecular Formula:C₂₄H₂₈O₇S
Molecular Weight:460.548
Hs Code.:

Synonyms:(6S,2'R)-6-(methoxymethoxy)-5,5-dimethyl-octa-2,7-diynoic acid 1-(toluene-4-sulfonyloxymethyl)-but-2-ynyl ester

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Chemical Property of (6S,2'R)-6-(methoxymethoxy)-5,5-dimethyl-octa-2,7-diynoic acid 1-(toluene-4-sulfonyloxymethyl)-but-2-ynyl ester

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Technology Process of (6S,2'R)-6-(methoxymethoxy)-5,5-dimethyl-octa-2,7-diynoic acid 1-(toluene-4-sulfonyloxymethyl)-but-2-ynyl ester

There total 8 articles about (6S,2'R)-6-(methoxymethoxy)-5,5-dimethyl-octa-2,7-diynoic acid 1-(toluene-4-sulfonyloxymethyl)-but-2-ynyl 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: 65.0%

: 1257866-17-3
(S)-6-(methoxymethoxy)-5,5-dimethyl-octa-2,7-diynoic acid

: 500596-41-8
(R)-toluene-4-sulfonic acid 2-hydroxy-pent-3-ynyl ester

: 1257866-18-4
(6S,2'R)-6-(methoxymethoxy)-5,5-dimethyl-octa-2,7-diynoic acid 1-(toluene-4-sulfonyloxymethyl)-but-2-ynyl ester

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at -78 - 20 ℃; Inert atmosphere;
DOI:10.1021/ol102432q

Reference yield:

: 1257866-12-8
4,4-dimethyl-1-(trimethylsilyl)hepta-1,6-diyne-3-one

: 1257866-18-4
(6S,2'R)-6-(methoxymethoxy)-5,5-dimethyl-octa-2,7-diynoic acid 1-(toluene-4-sulfonyloxymethyl)-but-2-ynyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: C₃₁H₃₀N₂O₂RuS / isopropyl alcohol / 16 h / 20 °C / Inert atmosphere

2.1: toluene-4-sulfonic acid; lithium bromide / 66 h / 20 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; hexane / -78 - -40 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

4.1: tetrabutylammonium nitrate / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere

5.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / -78 - 20 °C / Inert atmosphere

With dmap; n-butyllithium; C₃₁H₃₀N₂O₂RuS; tetrabutylammonium nitrate; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; lithium bromide; In tetrahydrofuran; hexane; dichloromethane; isopropyl alcohol;
DOI:10.1021/ol102432q

Reference yield:

: 1257866-21-9
(S)-4,4-dimethyl-1-(trimethylsilyl)hepta-1,6-diyne-3-ol

: 1257866-18-4
(6S,2'R)-6-(methoxymethoxy)-5,5-dimethyl-octa-2,7-diynoic acid 1-(toluene-4-sulfonyloxymethyl)-but-2-ynyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: toluene-4-sulfonic acid; lithium bromide / 66 h / 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / -78 - -40 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: tetrabutylammonium nitrate / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere

4.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / -78 - 20 °C / Inert atmosphere

With dmap; n-butyllithium; tetrabutylammonium nitrate; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; lithium bromide; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol102432q