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

Base Information

Chemical Name:benzyl (2S,3S,6R)-3-{[tert-butyl(diphenyl)silyl]oxy}-6-(8-ethoxy-8-oxooctyl)-2-methylpiperidine-1-carboxylate
CAS No.:622836-91-3
Molecular Formula:C₄₀H₅₅NO₅Si
Molecular Weight:657.966
Hs Code.:

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

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

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

There total 21 articles about benzyl (2S,3S,6R)-3-{[tert-butyl(diphenyl)silyl]oxy}-6-(8-ethoxy-8-oxooctyl)-2-methylpiperidine-1-carboxylate 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:

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

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

Guidance literature:: Multi-step reaction with 22 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

With 1H-imidazole; dmap; potassium hydroxide; sodium hydroxide; sodium periodate; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); (+)-(8,8-dichlorocamphorylsulfonyl)-oxaziridine; hydroxylamine hydrochloride; 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

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

Guidance literature:: Multi-step reaction with 19 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

With 1H-imidazole; potassium hydroxide; sodium hydroxide; sodium periodate; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); (+)-(8,8-dichlorocamphorylsulfonyl)-oxaziridine; hydroxylamine hydrochloride; 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

Reference yield:

: (5E,7E)-(S)-4-Benzyloxy-11-methoxymethoxy-undeca-5,7-dienoic acid

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

Guidance literature:: Multi-step reaction with 18 steps

1.1: diethyl ether / 0 °C

2.1: 88 percent / NH₂OH*HCl; KOH / methanol / 0 °C

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

4.1: 97 percent / H₂ / Pd/C / tetrahydrofuran

5.1: 99 percent / LiHMDS; (+)-[(8,8-dichlorocamphoryl)sulfonyl]oxaziridine / tetrahydrofuran / -78 °C

6.1: 73 percent / imidazole / dimethylformamide / 20 °C

7.1: tetrahydrofuran / 0 °C

8.1: NaBH₃CN; AcOH / tetrahydrofuran / 0 °C

9.1: 93 percent / Zn; aq. AcOH / 60 °C

10.1: H₂ / Pd(OH)2 / methanol

11.1: Na₂CO₃

12.1: aq. NaOH / methanol / 20 °C

13.1: NaH; imidazole / tetrahydrofuran / Heating

13.2: 93 percent / tetrahydrofuran / Heating

14.1: 99 percent / Bu₃SnH; AIBN / benzene / Heating

15.1: 73 percent / PPTS / 2-methyl-propan-2-ol / Heating

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

17.1: NaH / tetrahydrofuran / -20 °C

18.1: 76 percent / H₂ / ethyl acetate

With 1H-imidazole; potassium hydroxide; sodium hydroxide; sodium periodate; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); (+)-(8,8-dichlorocamphorylsulfonyl)-oxaziridine; hydroxylamine hydrochloride; 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; 16.1: Swern oxidation / 17.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ol030088w