6-{(2R,5S,6S)-1-[(benzyloxy)carbonyl]-5-hydroxy-6-methylpiperidine-2-yl}hexanoic acid

Base Information

Chemical Name:6-{(2R,5S,6S)-1-[(benzyloxy)carbonyl]-5-hydroxy-6-methylpiperidine-2-yl}hexanoic acid
CAS No.:622836-88-8
Molecular Formula:C₂₀H₂₉NO₅
Molecular Weight:363.454
Hs Code.:

Synonyms:6-{(2R,5S,6S)-1-[(benzyloxy)carbonyl]-5-hydroxy-6-methylpiperidine-2-yl}hexanoic acid

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Chemical Property of 6-{(2R,5S,6S)-1-[(benzyloxy)carbonyl]-5-hydroxy-6-methylpiperidine-2-yl}hexanoic acid

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Technology Process of 6-{(2R,5S,6S)-1-[(benzyloxy)carbonyl]-5-hydroxy-6-methylpiperidine-2-yl}hexanoic acid

There total 25 articles about 6-{(2R,5S,6S)-1-[(benzyloxy)carbonyl]-5-hydroxy-6-methylpiperidine-2-yl}hexanoic acid 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: 85.0%

: 1451067-49-4
methyl 6-{(2R,5S,6S)-1-[(benzyloxy)carbonyl]-5-hydroxy-6-methylpiperidine-2-yl}hexanoate

: 622836-88-8
6-{(2R,5S,6S)-1-[(benzyloxy)carbonyl]-5-hydroxy-6-methylpiperidine-2-yl}hexanoic acid

Guidance literature:: With barium hydroxide octahydrate; In methanol; at 40 ℃; for 48h;
DOI:10.1016/j.tet.2013.07.083

Reference yield:

: (2S,3S,6R)-3-(tert-Butyl-diphenyl-silanyloxy)-6-(5-carboxy-pentyl)-2-methyl-piperidine-1-carboxylic acid benzyl ester

: 622836-88-8
6-{(2R,5S,6S)-1-[(benzyloxy)carbonyl]-5-hydroxy-6-methylpiperidine-2-yl}hexanoic acid

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

: 622836-88-8
6-{(2R,5S,6S)-1-[(benzyloxy)carbonyl]-5-hydroxy-6-methylpiperidine-2-yl}hexanoic acid

Guidance literature:: Multi-step reaction with 21 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: PDC; molecular sieves 4 Angstroem / dimethylformamide / 20 °C

21.1: Bu₄NF / tetrahydrofuran / 20 °C

With 1H-imidazole; dmap; potassium hydroxide; sodium hydroxide; sodium periodate; dipyridinium dichromate; 2,2'-azobis(isobutyronitrile); (+)-(8,8-dichlorocamphorylsulfonyl)-oxaziridine; 4 A molecular sieve; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; hydrogen; iodine; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; sodium hydride; sodium cyanoborohydride; sodium carbonate; acetic acid; triethylamine; lithium hexamethyldisilazane; zinc; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;
DOI:10.1021/ol030088w