methyl (2'R,6'S)-8-(N-benzyloxycarbonyl-6'-methyl-5'-oxopiperidin-2'-yl)octanoate

Base Information

Chemical Name:methyl (2'R,6'S)-8-(N-benzyloxycarbonyl-6'-methyl-5'-oxopiperidin-2'-yl)octanoate
CAS No.:931405-39-9
Molecular Formula:C₂₃H₃₃NO₅
Molecular Weight:403.519
Hs Code.:

Synonyms:methyl (2'R,6'S)-8-(N-benzyloxycarbonyl-6'-methyl-5'-oxopiperidin-2'-yl)octanoate

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Chemical Property of methyl (2'R,6'S)-8-(N-benzyloxycarbonyl-6'-methyl-5'-oxopiperidin-2'-yl)octanoate

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Technology Process of methyl (2'R,6'S)-8-(N-benzyloxycarbonyl-6'-methyl-5'-oxopiperidin-2'-yl)octanoate

There total 6 articles about methyl (2'R,6'S)-8-(N-benzyloxycarbonyl-6'-methyl-5'-oxopiperidin-2'-yl)octanoate 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: 90.0%

: 931405-38-8
methyl (2'R,5'R,6'S)-8-(N-benzyloxycarbonyl-5'-hydroxy-6'-methylpiperidin-2'-yl)octanoate

: 931405-39-9
methyl (2'R,6'S)-8-(N-benzyloxycarbonyl-6'-methyl-5'-oxopiperidin-2'-yl)octanoate

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 2h;
DOI:10.1016/j.tetasy.2006.12.025

Reference yield:

: (4S)-3-benzyloxy-4-(N,N-dibenzylamino)pent-1-yne

: 931405-39-9
methyl (2'R,6'S)-8-(N-benzyloxycarbonyl-6'-methyl-5'-oxopiperidin-2'-yl)octanoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C

1.2: 61 percent / tetrahydrofuran; hexane / -78 - 0 °C

2.1: 81 percent / (COCl)2; DMSO; ethyldiisopropylamine / CH₂Cl₂ / 0.5 h / -78 - 20 °C

3.1: hydrogen / Pearlman's palladium hydroxide / methanol / 7 h / 20 °C

3.2: 78 percent / acetic acid; hydrogen / methanol / 12 h / 20 °C

4.1: 82 percent / NaHCO₃ / H₂O; dioxane / 24 h / 0 - 20 °C

5.1: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 - 20 °C

With n-butyllithium; oxalyl dichloride; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; palladium hydroxide - carbon; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; 2.1: Swern oxidation;
DOI:10.1016/j.tetasy.2006.12.025

Reference yield:

: methyl (13S)-12-benzyloxy-13-(N,N-dibenzylamino)-9-hydroxy-10-tetradecynoate

: 931405-39-9
methyl (2'R,6'S)-8-(N-benzyloxycarbonyl-6'-methyl-5'-oxopiperidin-2'-yl)octanoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 81 percent / (COCl)2; DMSO; ethyldiisopropylamine / CH₂Cl₂ / 0.5 h / -78 - 20 °C

2.1: hydrogen / Pearlman's palladium hydroxide / methanol / 7 h / 20 °C

2.2: 78 percent / acetic acid; hydrogen / methanol / 12 h / 20 °C

3.1: 82 percent / NaHCO₃ / H₂O; dioxane / 24 h / 0 - 20 °C

4.1: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 - 20 °C

With oxalyl dichloride; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; palladium hydroxide - carbon; In 1,4-dioxane; methanol; dichloromethane; water; 1.1: Swern oxidation;
DOI:10.1016/j.tetasy.2006.12.025