2-Benzenesulfonyl-pent-4-ynoic acid (1S,4R,6S)-6-isopropyl-4-methoxycarbonyloxy-3-methyl-cyclohex-2-enylmethyl ester

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Chemical Name:2-Benzenesulfonyl-pent-4-ynoic acid (1S,4R,6S)-6-isopropyl-4-methoxycarbonyloxy-3-methyl-cyclohex-2-enylmethyl ester
CAS No.:131250-65-2
Molecular Formula:C₂₄H₃₀O₇S
Molecular Weight:462.564
Hs Code.:

Synonyms:2-Benzenesulfonyl-pent-4-ynoic acid (1S,4R,6S)-6-isopropyl-4-methoxycarbonyloxy-3-methyl-cyclohex-2-enylmethyl ester

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Chemical Property of 2-Benzenesulfonyl-pent-4-ynoic acid (1S,4R,6S)-6-isopropyl-4-methoxycarbonyloxy-3-methyl-cyclohex-2-enylmethyl ester

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Technology Process of 2-Benzenesulfonyl-pent-4-ynoic acid (1S,4R,6S)-6-isopropyl-4-methoxycarbonyloxy-3-methyl-cyclohex-2-enylmethyl ester

There total 9 articles about 2-Benzenesulfonyl-pent-4-ynoic acid (1S,4R,6S)-6-isopropyl-4-methoxycarbonyloxy-3-methyl-cyclohex-2-enylmethyl 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: 98.0%

: 131273-41-1
Carbonic acid (1R,4S,5S)-4-hydroxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl ester methyl ester

: 131250-57-2
2-Benzenesulfonyl-pent-4-ynoic acid

: 131250-65-2
2-Benzenesulfonyl-pent-4-ynoic acid (1S,4R,6S)-6-isopropyl-4-methoxycarbonyloxy-3-methyl-cyclohex-2-enylmethyl ester

Guidance literature:: With dicyclohexyl-carbodiimide; In dichloromethane; from 0 deg C to RT;
DOI:10.1021/ja00002a043

Reference yield:

: 35644-75-8,208397-90-4
(1R,4R,6R)-4-Isopropyl-1-methyl-7-oxa-bicyclo[4.1.0]heptan-2-one

: 131250-65-2
2-Benzenesulfonyl-pent-4-ynoic acid (1S,4R,6S)-6-isopropyl-4-methoxycarbonyloxy-3-methyl-cyclohex-2-enylmethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) LDA / 1.) THF, -78 deg C,

2: 95 percent / (C₂H₅)3N, DMAP / CH₂Cl₂

3: 91 percent / L-selectride / tetrahydrofuran / -78 °C

4: 85 percent / (C₂H₅)3N / CH₂Cl₂ / 0 °C

5: 90 percent / NaC₁₀H₈ / tetrahydrofuran / Ambient temperature

6: 1.) n-C₄H₉Li / 1.) ether, hexane, 2.) 0 deg C

7: 90 percent / TBAF / tetrahydrofuran / Ambient temperature

8: 98 percent / DCC / CH₂Cl₂ / from 0 deg C to RT

With dmap; n-butyllithium; NaC₁₀H₈; tetrabutyl ammonium fluoride; L-Selectride; triethylamine; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00002a043

Reference yield:

: 33375-08-5
(R)-5-isopropyl-2-methylcyclohex-2-enone

: 131250-65-2
2-Benzenesulfonyl-pent-4-ynoic acid (1S,4R,6S)-6-isopropyl-4-methoxycarbonyloxy-3-methyl-cyclohex-2-enylmethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 93 percent / H₂O₂, NaOH / methanol

2: 1.) LDA / 1.) THF, -78 deg C,

3: 95 percent / (C₂H₅)3N, DMAP / CH₂Cl₂

4: 91 percent / L-selectride / tetrahydrofuran / -78 °C

5: 85 percent / (C₂H₅)3N / CH₂Cl₂ / 0 °C

6: 90 percent / NaC₁₀H₈ / tetrahydrofuran / Ambient temperature

7: 1.) n-C₄H₉Li / 1.) ether, hexane, 2.) 0 deg C

8: 90 percent / TBAF / tetrahydrofuran / Ambient temperature

9: 98 percent / DCC / CH₂Cl₂ / from 0 deg C to RT

With dmap; sodium hydroxide; n-butyllithium; NaC₁₀H₈; tetrabutyl ammonium fluoride; dihydrogen peroxide; L-Selectride; triethylamine; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ja00002a043