(2R,3R,4S)-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2,4-dimethyl-2-phenylselanyl-pentanoic acid methyl ester

Base Information

• Chemical Name: (2R,3R,4S)-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2,4-dimethyl-2-phenylselanyl-pentanoic acid methyl ester
• CAS No.: 367264-25-3
• Molecular Formula: C₃₀H₃₈O₄SeSi
• Molecular Weight: 569.675

Synonyms:(2R,3R,4S)-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2,4-dimethyl-2-phenylselanyl-pentanoic acid methyl ester

Chemical Property of (2R,3R,4S)-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2,4-dimethyl-2-phenylselanyl-pentanoic acid methyl ester

Chemical Property:

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Technology Process of (2R,3R,4S)-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2,4-dimethyl-2-phenylselanyl-pentanoic acid methyl ester

There total 2 articles about (2R,3R,4S)-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2,4-dimethyl-2-phenylselanyl-pentanoic acid methyl 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:

(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal (92817-88-4) + (E)-(1-methoxy-2-phenylselanyl-propenyloxy)-trimethyl-silane (367264-12-8) → (2R,3S,4S)-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2,4-dimethyl-2-phenylselanyl-pentanoic acid methyl ester + (2S,3S,4S)-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2,4-dimethyl-2-phenylselanyl-pentanoic acid methyl ester + (2R,3R,4S)-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2,4-dimethyl-2-phenylselanyl-pentanoic acid methyl ester (367264-25-3) + (2S,3R,4S)-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2,4-dimethyl-2-phenylselanyl-pentanoic acid methyl ester

Guidance literature:

With dimethylaluminum chloride; In hexane; dichloromethane; at -78 ℃; for 0.166667h; Title compound not separated from byproducts.;

DOI:10.1021/ja010805m

Reference yield:

methyl α-(phenylseleno)propionate (65275-66-3) → (2R,3R,4S)-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2,4-dimethyl-2-phenylselanyl-pentanoic acid methyl ester (367264-25-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: tetrahydrofuran; hexane / 1 h / 25 °C

2.1: Me₂AlCl / CH₂Cl₂; hexane / 0.17 h / -78 °C

With dimethylaluminum chloride; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; 2.1: Mukaiyama reaction;

DOI:10.1021/ja010805m

Reference yield: 87.0%

(2R,3R,4S)-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2,4-dimethyl-2-phenylselanyl-pentanoic acid methyl ester (367264-25-3) → (3R,4R,5S)-4-hydroxy-3,5-dimethyl-3-phenylselanyl-tetrahydro-pyran-2-one

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; at 23 ℃; for 12h;

DOI:10.1021/ja010805m

upstream raw materials:

(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal

(E)-(1-methoxy-2-phenylselanyl-propenyloxy)-trimethyl-silane

methyl α-(phenylseleno)propionate

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