((2R,4S,5R,6R)-2-Methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-oxo-acetic acid 2-trimethylsilanyl-ethyl ester

Base Information

Chemical Name:((2R,4S,5R,6R)-2-Methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-oxo-acetic acid 2-trimethylsilanyl-ethyl ester
CAS No.:111194-20-8
Molecular Formula:C₂₂H₃₄O₅SeSi
Molecular Weight:485.554
Hs Code.:

Synonyms:((2R,4S,5R,6R)-2-Methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-oxo-acetic acid 2-trimethylsilanyl-ethyl ester

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Chemical Property of ((2R,4S,5R,6R)-2-Methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-oxo-acetic acid 2-trimethylsilanyl-ethyl ester

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Technology Process of ((2R,4S,5R,6R)-2-Methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-oxo-acetic acid 2-trimethylsilanyl-ethyl ester

There total 12 articles about ((2R,4S,5R,6R)-2-Methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-oxo-acetic acid 2-trimethylsilanyl-ethyl ester 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: 90.0%

: 111194-18-4,111194-19-5
(R)-Hydroxy-((2R,4S,5R,6R)-2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-acetic acid 2-trimethylsilanyl-ethyl ester

: 111194-20-8
((2R,4S,5R,6R)-2-Methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-oxo-acetic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:: With triethylamine; Cl₂*Me₂S; In dichloromethane; at -70 ℃; for 1.5h;
DOI:10.1039/c39870000106

Reference yield:

: 41998-65-6,52884-22-7,52884-23-8,104996-28-3,113083-45-7,113083-46-8,119365-32-1
(2R*,3R*)-3-methyl-4-pentyne-2-ol

: 111194-20-8
((2R,4S,5R,6R)-2-Methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-oxo-acetic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1) n-BuLi

2: 85 percent / H₂, quinoline / Pd/BaSO₄ (5percent) / ethanol / 1 h

3: 89 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / -85 °C

4: 1) LDA / hexane, THF, -75 deg C, 1) 1 h, 2) 2.5 h

5: conc. HCl / tetrahydrofuran; H₂O / 0.33 h / Ambient temperature

6: 1) p-TsOH, 2) oxalyl chloride, DMSO, Et₃N / 1) 3.5h, r.t., 2) CH₂Cl₂, -70 to 0 degC, 1.5h

With quinoline; hydrogenchloride; n-butyllithium; oxalyl dichloride; hydrogen; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; Pd-BaSO₄; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; water;
DOI:10.1016/S0040-4020(01)81980-3

Reference yield:

: 66186-46-7,66791-79-5,105087-16-9,129213-89-4
(4R*,5R*)-4-methyl-5-hydroxy-2-hexynoic acid

: 111194-20-8
((2R,4S,5R,6R)-2-Methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-oxo-acetic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 85 percent / H₂, quinoline / Pd/BaSO₄ (5percent) / ethanol / 1 h

2: 89 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / -85 °C

3: 1) LDA / hexane, THF, -75 deg C, 1) 1 h, 2) 2.5 h

4: conc. HCl / tetrahydrofuran; H₂O / 0.33 h / Ambient temperature

5: 1) p-TsOH, 2) oxalyl chloride, DMSO, Et₃N / 1) 3.5h, r.t., 2) CH₂Cl₂, -70 to 0 degC, 1.5h

With quinoline; hydrogenchloride; n-butyllithium; oxalyl dichloride; hydrogen; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; Pd-BaSO₄; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; water;
DOI:10.1016/S0040-4020(01)81980-3