methyl (2S,3R,5R,6S)-(+)-2-(tert-butyldiphenylsilyloxymethyl)-3,5-diethyl-6-(3-hydroxypropyl)piperidine-1-carboxylate

Base Information

Chemical Name:methyl (2S,3R,5R,6S)-(+)-2-(tert-butyldiphenylsilyloxymethyl)-3,5-diethyl-6-(3-hydroxypropyl)piperidine-1-carboxylate
CAS No.:442202-18-8
Molecular Formula:C₃₁H₄₇NO₄Si
Molecular Weight:525.804
Hs Code.:

Synonyms:methyl (2S,3R,5R,6S)-(+)-2-(tert-butyldiphenylsilyloxymethyl)-3,5-diethyl-6-(3-hydroxypropyl)piperidine-1-carboxylate

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Chemical Property of methyl (2S,3R,5R,6S)-(+)-2-(tert-butyldiphenylsilyloxymethyl)-3,5-diethyl-6-(3-hydroxypropyl)piperidine-1-carboxylate

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Technology Process of methyl (2S,3R,5R,6S)-(+)-2-(tert-butyldiphenylsilyloxymethyl)-3,5-diethyl-6-(3-hydroxypropyl)piperidine-1-carboxylate

There total 23 articles about methyl (2S,3R,5R,6S)-(+)-2-(tert-butyldiphenylsilyloxymethyl)-3,5-diethyl-6-(3-hydroxypropyl)piperidine-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: 98.0%

: 442202-29-1
methyl (2S,3R,5S,6R)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-3-ethyl-6-(2-ethoxycarbonylvinyl)-5-vinylpiperidine-1-carboxylate

: 442202-18-8
methyl (2S,3R,5R,6S)-(+)-2-(tert-butyldiphenylsilyloxymethyl)-3,5-diethyl-6-(3-hydroxypropyl)piperidine-1-carboxylate

Guidance literature:: methyl (2S,3R,5S,6R)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-3-ethyl-6-(2-ethoxycarbonylvinyl)-5-vinylpiperidine-1-carboxylate; With hydrogen; palladium on activated charcoal; In ethyl acetate; for 72h; under 760 Torr;

With lithium triethylborohydride; In tetrahydrofuran; at 0 ℃; for 1h;
DOI:10.1016/j.tet.2004.05.039

Reference yield:

: 117935-51-0
(R)-1-O-acetyl-2-ethyl-1,3-propanediol

: 442202-18-8
methyl (2S,3R,5R,6S)-(+)-2-(tert-butyldiphenylsilyloxymethyl)-3,5-diethyl-6-(3-hydroxypropyl)piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 20 steps

1.1: PPTS / CH₂Cl₂ / 2 h / 20 °C

2.1: K₂CO₃ / methanol / 3 h / 20 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

4.2: 695 mg / tetrahydrofuran; hexane / 1.5 h / 20 °C

5.1: 80 percent / (DHQD)2PYR; K₂OsO₄*2H₂O; K₃Fe(CN)6 / K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 24 h / 0 °C

6.1: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 20 h / 20 °C

7.1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

8.1: 1.3 g / NaN₃ / dimethylformamide / 15 h / 80 °C

9.1: PPTS / ethanol / 2 h / 60 °C

10.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

11.1: NaH / tetrahydrofuran / 0.25 h / 0 °C

11.2: 935 mg / tetrahydrofuran / 2 h / 20 °C

12.1: 73 percent / H₂ / Pd-C / ethyl acetate / 72 h / 3040 Torr

13.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

13.2: 97 percent / tetrahydrofuran; hexane / 1 h / -78 - 0 °C

14.1: hexamethyldisilazane; n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

14.2: 97 percent / tetrahydrofuran; hexane / 1 h / -78 - -45 °C

15.1: 75 percent / Pd(Ph₃P)4; Et₃N / dimethylformamide / 14 h / 70 °C

16.1: MeLi / diethyl ether / 0.5 h / 0 °C

16.2: CuI / diethyl ether / 0.33 h / -78 - -35 °C

16.3: 95 percent / diethyl ether / 1 h / -78 - -20 °C

17.1: 96 percent / Super-Hydride / tetrahydrofuran / 1 h / 0 °C

18.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

19.1: NaH / tetrahydrofuran / 0.25 h / 0 °C

19.2: 1.05 g / tetrahydrofuran / 2 h / 20 °C

20.1: H₂ / Pd-C / ethyl acetate / 72 h / 760 Torr

20.2: 98 percent / Super-Hydride / tetrahydrofuran / 1 h / 0 °C

With dmap; potassium osmate(VI); tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; sodium azide; oxalyl dichloride; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; methyllithium; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; lithium triethylborohydride; potassium carbonate; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; potassium hexacyanoferrate(III); palladium on activated charcoal; potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; 3.1: Swern oxidation / 4.2: Wittig reaction / 10.1: Swern oxidation / 11.2: Horner-Emmons reaction / 18.1: Swern oxidation / 19.2: Horner-Emmons reaction;
DOI:10.1016/j.tet.2004.05.039

Reference yield:

: 442202-14-4
dimethyl (5R,6S)-(-)-6-(tert-butyldiphenylsilyloxymethyl)-5-ethyl-5,6-dihydro-4H-pyridine-1,2-dicarboxylate

: 442202-18-8
methyl (2S,3R,5R,6S)-(+)-2-(tert-butyldiphenylsilyloxymethyl)-3,5-diethyl-6-(3-hydroxypropyl)piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: MeLi / diethyl ether / 0.5 h / 0 °C

1.2: CuI / diethyl ether / 0.33 h / -78 - -35 °C

1.3: 95 percent / diethyl ether / 1 h / -78 - -20 °C

2.1: 96 percent / Super-Hydride / tetrahydrofuran / 1 h / 0 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

4.1: NaH / tetrahydrofuran / 0.25 h / 0 °C

4.2: 1.05 g / tetrahydrofuran / 2 h / 20 °C

5.1: H₂ / Pd-C / ethyl acetate / 72 h / 760 Torr

5.2: 98 percent / Super-Hydride / tetrahydrofuran / 1 h / 0 °C

With oxalyl dichloride; methyllithium; hydrogen; sodium hydride; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; 3.1: Swern oxidation / 4.2: Horner-Emmons reaction;
DOI:10.1016/j.tet.2004.05.039