methyl (8R,9R)-(-)-8-methyl-3-oxo-5-phenylsulfanylhexahydrooxazolo[3,4-a]pyridine-5-carboxylate

Base Information

Chemical Name:methyl (8R,9R)-(-)-8-methyl-3-oxo-5-phenylsulfanylhexahydrooxazolo[3,4-a]pyridine-5-carboxylate
CAS No.:619267-06-0
Molecular Formula:C₁₆H₁₉NO₄S
Molecular Weight:321.397
Hs Code.:

Synonyms:methyl (8R,9R)-(-)-8-methyl-3-oxo-5-phenylsulfanylhexahydrooxazolo[3,4-a]pyridine-5-carboxylate

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Chemical Property of methyl (8R,9R)-(-)-8-methyl-3-oxo-5-phenylsulfanylhexahydrooxazolo[3,4-a]pyridine-5-carboxylate

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Technology Process of methyl (8R,9R)-(-)-8-methyl-3-oxo-5-phenylsulfanylhexahydrooxazolo[3,4-a]pyridine-5-carboxylate

There total 11 articles about methyl (8R,9R)-(-)-8-methyl-3-oxo-5-phenylsulfanylhexahydrooxazolo[3,4-a]pyridine-5-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: 99.0%

: 882-33-7
diphenyldisulfane

: 619266-93-2
methyl (5S,8R,9R)-(-)-8-methyl-3-oxohexahydrooxazolo[3,4-a]pyridine-5-carboxylate

: 619267-06-0
methyl (8R,9R)-(-)-8-methyl-3-oxo-5-phenylsulfanylhexahydrooxazolo[3,4-a]pyridine-5-carboxylate

Guidance literature:: methyl (5S,8R,9R)-(-)-8-methyl-3-oxohexahydrooxazolo[3,4-a]pyridine-5-carboxylate; With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

diphenyldisulfane; In tetrahydrofuran; hexane; at -78 - 0 ℃;
DOI:10.1016/j.tet.2004.05.039

Reference yield:

: 209257-75-0
(S)-6-((tert-butyldiphenylsilyloxy)methyl)piperidin-2-one

: 619267-06-0
methyl (8R,9R)-(-)-8-methyl-3-oxo-5-phenylsulfanylhexahydrooxazolo[3,4-a]pyridine-5-carboxylate

Guidance literature:: Multi-step reaction with 11 steps

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

1.2: 98 percent / tetrahydrofuran; hexane / 2 h / -78 - 0 °C

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

2.2: 96 percent / tetrahydrofuran; hexane / 1 h / -78 - -40 °C

3.1: 88 percent / Pd(PPh₃)4 / dimethylformamide / 15 h / 70 °C

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

4.2: 98 percent / diethyl ether / -78 - -35 °C

5.1: 92 percent / Super-Hydride / tetrahydrofuran / 1 h / 0 °C

6.1: 99 percent / NaH / tetrahydrofuran / 1 h / 0 °C

7.1: 99 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

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

9.1: NaH₂PO₄; 2-methyl-2-butene; aq. NaClO₂ / 2-methyl-propan-2-ol / 0.5 h / 20 °C

10.1: 1.06 g / ethyl acetate; diethyl ether / 23 h / 20 °C

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

11.2: 99 percent / tetrahydrofuran; hexane / -78 - 0 °C

With sodium chlorite; sodium dihydrogenphosphate; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydride; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; 8.1: Swern oxidation;
DOI:10.1016/j.tet.2004.05.039

Reference yield:

: 442202-20-2
methyl (6S)-(-)-2-(tert-butyldiphenylsilyloxymethyl)-6-oxopiperidine-1-carboxylate

: 619267-06-0
methyl (8R,9R)-(-)-8-methyl-3-oxo-5-phenylsulfanylhexahydrooxazolo[3,4-a]pyridine-5-carboxylate

Guidance literature:: Multi-step reaction with 10 steps

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

1.2: 96 percent / tetrahydrofuran; hexane / 1 h / -78 - -40 °C

2.1: 88 percent / Pd(PPh₃)4 / dimethylformamide / 15 h / 70 °C

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

3.2: 98 percent / diethyl ether / -78 - -35 °C

4.1: 92 percent / Super-Hydride / tetrahydrofuran / 1 h / 0 °C

5.1: 99 percent / NaH / tetrahydrofuran / 1 h / 0 °C

6.1: 99 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

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

8.1: NaH₂PO₄; 2-methyl-2-butene; aq. NaClO₂ / 2-methyl-propan-2-ol / 0.5 h / 20 °C

9.1: 1.06 g / ethyl acetate; diethyl ether / 23 h / 20 °C

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

10.2: 99 percent / tetrahydrofuran; hexane / -78 - 0 °C

With sodium chlorite; sodium dihydrogenphosphate; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydride; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; 7.1: Swern oxidation;
DOI:10.1016/j.tet.2004.05.039