8-{(2S,5S,6S)-1-[(benzyloxy)carbonyl]-5-hydroxy-6-methylpiperidinyl}octanoic acid

Base Information

Chemical Name:8-{(2S,5S,6S)-1-[(benzyloxy)carbonyl]-5-hydroxy-6-methylpiperidinyl}octanoic acid
CAS No.:55438-00-1
Molecular Formula:C₂₂H₃₃NO₅
Molecular Weight:391.508
Hs Code.:

Synonyms:8-{(2S,5S,6S)-1-[(benzyloxy)carbonyl]-5-hydroxy-6-methylpiperidinyl}octanoic acid

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Chemical Property of 8-{(2S,5S,6S)-1-[(benzyloxy)carbonyl]-5-hydroxy-6-methylpiperidinyl}octanoic acid

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Technology Process of 8-{(2S,5S,6S)-1-[(benzyloxy)carbonyl]-5-hydroxy-6-methylpiperidinyl}octanoic acid

There total 45 articles about 8-{(2S,5S,6S)-1-[(benzyloxy)carbonyl]-5-hydroxy-6-methylpiperidinyl}octanoic 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: 97.0%

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

: 55438-00-1
8-{(2S,5S,6S)-1-[(benzyloxy)carbonyl]-5-hydroxy-6-methylpiperidinyl}octanoic acid

Guidance literature:: With barium dihydroxide; In methanol; at 20 ℃;
DOI:10.1021/ol030088w

Reference yield: 81.0%

: 477945-90-7
(2S,3S,6R)-6-(7-Carboxy-heptyl)-3-(dimethyl-phenyl-silanyl)-2-methyl-piperidine-1-carboxylic acid benzyl ester

: 55438-00-1
8-{(2S,5S,6S)-1-[(benzyloxy)carbonyl]-5-hydroxy-6-methylpiperidinyl}octanoic acid

Guidance literature:: With peracetic acid; potassium bromide; at 20 - 40 ℃;
DOI:10.1016/S0040-4039(02)01853-1

Reference yield:

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

: 55438-00-1
8-{(2S,5S,6S)-1-[(benzyloxy)carbonyl]-5-hydroxy-6-methylpiperidinyl}octanoic acid

Guidance literature:: Multi-step reaction with 24 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

24.1: 97 percent / Ba(OH)2*8H₂O / methanol / 20 °C

With 1H-imidazole; dmap; barium dihydroxide; 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