(2S,3S,6R)-6-(7-Ethoxycarbonyl-heptyl)-3-hydroxy-2-methyl-piperidine-1-carboxylic acid benzyl ester

Base Information

Chemical Name:(2S,3S,6R)-6-(7-Ethoxycarbonyl-heptyl)-3-hydroxy-2-methyl-piperidine-1-carboxylic acid benzyl ester
CAS No.:676565-29-0
Molecular Formula:C₂₄H₃₇NO₅
Molecular Weight:419.561
Hs Code.:

Synonyms:(2S,3S,6R)-6-(7-Ethoxycarbonyl-heptyl)-3-hydroxy-2-methyl-piperidine-1-carboxylic acid benzyl ester

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Chemical Property of (2S,3S,6R)-6-(7-Ethoxycarbonyl-heptyl)-3-hydroxy-2-methyl-piperidine-1-carboxylic acid benzyl ester

Chemical Property:

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Technology Process of (2S,3S,6R)-6-(7-Ethoxycarbonyl-heptyl)-3-hydroxy-2-methyl-piperidine-1-carboxylic acid benzyl ester

There total 23 articles about (2S,3S,6R)-6-(7-Ethoxycarbonyl-heptyl)-3-hydroxy-2-methyl-piperidine-1-carboxylic acid benzyl 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: 97.0%

: 622836-91-3
benzyl (2S,3S,6R)-3-{[tert-butyl(diphenyl)silyl]oxy}-6-(8-ethoxy-8-oxooctyl)-2-methylpiperidine-1-carboxylate

: 676565-29-0
(2S,3S,6R)-6-(7-Ethoxycarbonyl-heptyl)-3-hydroxy-2-methyl-piperidine-1-carboxylic acid benzyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;
DOI:10.1021/ol030088w

Reference yield:

: (3S,6E)-3-(benzyloxy)-10-(methoxymethoxy)deca-4,6-dien-1-ol

: 676565-29-0
(2S,3S,6R)-6-(7-Ethoxycarbonyl-heptyl)-3-hydroxy-2-methyl-piperidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 23 steps

1.1: 91 percent / Et₃N; DMAP / CH₂Cl₂ / 20 °C

2.1: 94 percent / I₂ / benzene / Irradiation

3.1: 95 percent / dimethylsulfoxide / 50 °C

4.1: NaOH / methanol; H₂O / Heating

5.1: diethyl ether / 0 °C

6.1: 88 percent / NH₂OH*HCl; KOH / methanol / 0 °C

7.1: NaIO₄ / H₂O; dimethylformamide / 0.25 h / 0 °C

8.1: 97 percent / H₂ / Pd/C / tetrahydrofuran

9.1: 99 percent / LiHMDS; (+)-[(8,8-dichlorocamphoryl)sulfonyl]oxaziridine / tetrahydrofuran / -78 °C

10.1: 73 percent / imidazole / dimethylformamide / 20 °C

11.1: tetrahydrofuran / 0 °C

12.1: NaBH₃CN; AcOH / tetrahydrofuran / 0 °C

13.1: 93 percent / Zn; aq. AcOH / 60 °C

14.1: H₂ / Pd(OH)2 / methanol

15.1: Na₂CO₃

16.1: aq. NaOH / methanol / 20 °C

17.1: NaH; imidazole / tetrahydrofuran / Heating

17.2: 93 percent / tetrahydrofuran / Heating

18.1: 99 percent / Bu₃SnH; AIBN / benzene / Heating

19.1: 73 percent / PPTS / 2-methyl-propan-2-ol / Heating

20.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

21.1: NaH / tetrahydrofuran / -20 °C

22.1: 76 percent / H₂ / ethyl acetate

23.1: 97 percent / Bu₄NF / tetrahydrofuran / 20 °C

With 1H-imidazole; dmap; potassium hydroxide; sodium hydroxide; sodium periodate; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); (+)-(8,8-dichlorocamphorylsulfonyl)-oxaziridine; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; hydrogen; iodine; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; sodium hydride; sodium cyanoborohydride; sodium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; zinc; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 20.1: Swern oxidation / 21.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ol030088w

Reference yield:

: 622836-80-0
(5E,7E)-(S)-4-Benzyloxy-11-methoxymethoxy-undeca-5,7-dienenitrile

: 676565-29-0
(2S,3S,6R)-6-(7-Ethoxycarbonyl-heptyl)-3-hydroxy-2-methyl-piperidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 20 steps

1.1: NaOH / methanol; H₂O / Heating

2.1: diethyl ether / 0 °C

3.1: 88 percent / NH₂OH*HCl; KOH / methanol / 0 °C

4.1: NaIO₄ / H₂O; dimethylformamide / 0.25 h / 0 °C

5.1: 97 percent / H₂ / Pd/C / tetrahydrofuran

6.1: 99 percent / LiHMDS; (+)-[(8,8-dichlorocamphoryl)sulfonyl]oxaziridine / tetrahydrofuran / -78 °C

7.1: 73 percent / imidazole / dimethylformamide / 20 °C

8.1: tetrahydrofuran / 0 °C

9.1: NaBH₃CN; AcOH / tetrahydrofuran / 0 °C

10.1: 93 percent / Zn; aq. AcOH / 60 °C

11.1: H₂ / Pd(OH)2 / methanol

12.1: Na₂CO₃

13.1: aq. NaOH / methanol / 20 °C

14.1: NaH; imidazole / tetrahydrofuran / Heating

14.2: 93 percent / tetrahydrofuran / Heating

15.1: 99 percent / Bu₃SnH; AIBN / benzene / Heating

16.1: 73 percent / PPTS / 2-methyl-propan-2-ol / Heating

17.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

18.1: NaH / tetrahydrofuran / -20 °C

19.1: 76 percent / H₂ / ethyl acetate

20.1: 97 percent / Bu₄NF / tetrahydrofuran / 20 °C

With 1H-imidazole; potassium hydroxide; sodium hydroxide; sodium periodate; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); (+)-(8,8-dichlorocamphorylsulfonyl)-oxaziridine; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; sodium hydride; sodium cyanoborohydride; sodium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; zinc; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 17.1: Swern oxidation / 18.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ol030088w