((2S,3S,5R,8aR)-1-benzyl-3-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinyl)methanol

Base Information

Chemical Name:((2S,3S,5R,8aR)-1-benzyl-3-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinyl)methanol
CAS No.:303191-14-2
Molecular Formula:C₂₄H₃₉NO₂Si
Molecular Weight:401.665
Hs Code.:

Synonyms:((2S,3S,5R,8aR)-1-benzyl-3-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinyl)methanol

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Chemical Property of ((2S,3S,5R,8aR)-1-benzyl-3-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinyl)methanol

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Technology Process of ((2S,3S,5R,8aR)-1-benzyl-3-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinyl)methanol

There total 44 articles about ((2S,3S,5R,8aR)-1-benzyl-3-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinyl)methanol 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: 88.0%

: 345897-03-2
methyl (2S,3S,5R,8aR)-1-benzoyl-3-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinecarboxylate

: 303191-14-2
((2S,3S,5R,8aR)-1-benzyl-3-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinyl)methanol

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; for 0.25h; Heating;
DOI:10.1021/jo001589n

Reference yield:

: (2S,4aR,5S)-5-Benzyloxy-7-hydroxy-2-(2-methoxymethoxy-ethyl)-hexahydro-pyrido[1,2-b][1,2]oxazin-8-one

: 303191-14-2
((2S,3S,5R,8aR)-1-benzyl-3-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinyl)methanol

Guidance literature:: Multi-step reaction with 16 steps

1.1: imidazole / dimethylformamide / 42 h / 20 °C

2.1: tetrahydrofuran / 0.17 h / 0 °C

2.2: 82 percent / NaBH₃CN; AcOH / tetrahydrofuran / 1 h / 0 °C

3.1: Zn; AcOH / H₂O / 1 h / 60 °C / 7

4.1: 90 percent / KOH; K₂CO₃ / CH₂Cl₂; H₂O / 1 h / 0 °C

5.1: NaH; imidazole / tetrahydrofuran / 1 h / Heating

5.2: 98 percent / tetrahydrofuran / 0.5 h / Heating

6.1: 95 percent / tributyltinhydride; 2,2-azobisisobutyronitrile / benzene / 3 h / Heating

7.1: 81 percent / pyridinium p-toluenesulfonate / 2-methyl-propan-2-ol / 3 h / Heating

8.1: 95 percent / H₂ / Pd(OH)2 / methanol / 1.5 h

9.1: 94 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -78 - 20 °C

10.1: 87 percent / AcOH; piperidine / benzene / 1 h / Heating

11.1: pyridinium dichromate / dimethylformamide / 12 h / 20 °C

12.1: 75 percent / diethyl ether / 0 °C

13.1: 84 percent / thionyl chloride; triethylamine / CH₂Cl₂ / 0.25 h / 0 °C

14.1: Bu₄NF / tetrahydrofuran / 120 h / 20 °C

15.1: 99 percent / imidazole / dimethylformamide / 1 h / 50 °C

16.1: 88 percent / LiAlH₄ / tetrahydrofuran / 0.25 h / Heating

With piperidine; 1H-imidazole; potassium hydroxide; lithium aluminium tetrahydride; dipyridinium dichromate; thionyl chloride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; zinc; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 9.1: Swern oxidation;
DOI:10.1021/jo001589n

Reference yield:

: (2S,4aR,5S,7S,8S)-5-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-2-(2-methoxymethoxy-ethyl)-8-methyl-octahydro-pyrido[1,2-b][1,2]oxazine

: 303191-14-2
((2S,3S,5R,8aR)-1-benzyl-3-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-1,2,3,5,6,7,8,8a-octahydro-5-quinolinyl)methanol

Guidance literature:: Multi-step reaction with 15 steps

1.1: Zn; aq. AcOH / 60 °C

2.2: aq. KOH

3.1: NaH; imidazole

3.2: 98 percent / tetrahydrofuran

4.1: Bu₃SnH; AIBN / benzene / Heating

5.1: PPTS / 2-methyl-propan-2-ol / Heating

6.1: H₂ / Pd(OH)2 / methanol

7.1: (COCl)2; DMSO; Et₃N / -89 - 0 °C

8.1: 87 percent / piperidine; AcOH / benzene / Heating

9.1: PDC / dimethylformamide

10.1: diethyl ether

11.1: 84 percent / SOCl₂; Et₃N

12.1: Bu₄NF / tetrahydrofuran / 20 °C

13.1: Bu₄NF / tetrahydrofuran / 120 h / 20 °C

14.1: imidazole / dimethylformamide

15.1: LiAlH₄ / tetrahydrofuran / Heating

With piperidine; 1H-imidazole; lithium aluminium tetrahydride; dipyridinium dichromate; thionyl chloride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; zinc; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 1.1: reductive ring cleavage / 2.1: Acylation / 2.2: Hydrolysis / 3.1: Addition / 3.2: Methylation / 4.1: deoxygenation / 5.1: ether cleavage / 6.1: Hydrogenolysis / 7.1: Swern oxidation / 8.1: Cyclization / 9.1: Oxidation / 10.1: Methylation / 11.1: Dehydration / 12.1: desilylation; epimerization / 13.1: epimerization / 14.1: silylation / 15.1: Reduction;
DOI:10.1021/ol000153r