(2R,3S)-5-(tert-Butyl-diphenyl-silanyloxy)-2,3-dihydroxy-pentanoic acid ethyl ester

Base Information

Chemical Name:(2R,3S)-5-(tert-Butyl-diphenyl-silanyloxy)-2,3-dihydroxy-pentanoic acid ethyl ester
CAS No.:562823-69-2
Molecular Formula:C₂₃H₃₂O₅Si
Molecular Weight:416.59
Hs Code.:

Synonyms:(2R,3S)-5-(tert-Butyl-diphenyl-silanyloxy)-2,3-dihydroxy-pentanoic acid ethyl ester

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Chemical Property of (2R,3S)-5-(tert-Butyl-diphenyl-silanyloxy)-2,3-dihydroxy-pentanoic acid ethyl ester

Chemical Property:

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Technology Process of (2R,3S)-5-(tert-Butyl-diphenyl-silanyloxy)-2,3-dihydroxy-pentanoic acid ethyl ester

There total 1 articles about (2R,3S)-5-(tert-Butyl-diphenyl-silanyloxy)-2,3-dihydroxy-pentanoic acid 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:

: 256494-25-4
(E)-ethyl 5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-enoate

: 562823-69-2
(2R,3S)-5-(tert-Butyl-diphenyl-silanyloxy)-2,3-dihydroxy-pentanoic acid ethyl ester

: ethyl (2S,3R)-5-[1-(tert-butyl)-1,1-diphenylsilyl]oxy-2,3-dihydroxypentanoate

Guidance literature:: With AD-mix-α; methanesulfonamide; In water; tert-butyl alcohol; at 0 ℃; for 36h; Title compound not separated from byproducts;
DOI:10.1016/S0040-4039(03)00744-5

Reference yield: 92.0%

: 77-76-9
2,2-dimethoxy-propane

: 562823-69-2
(2R,3S)-5-(tert-Butyl-diphenyl-silanyloxy)-2,3-dihydroxy-pentanoic acid ethyl ester

: 562823-70-5
(4R,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester

Guidance literature:: With pyridinium p-toluenesulfonate; In acetone; at 23 ℃; for 5h;
DOI:10.1016/S0040-4039(03)00744-5

Reference yield:

: 562823-69-2
(2R,3S)-5-(tert-Butyl-diphenyl-silanyloxy)-2,3-dihydroxy-pentanoic acid ethyl ester

: 562823-66-9
(2S,3S,5S)-6-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-hexanoic acid methyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 92 percent / PPTS / acetone / 5 h / 23 °C

2: 97 percent / LiBH₄ / tetrahydrofuran / 2 h / 0 °C

3: 69 percent / NaH / dimethylformamide / 4 h / 23 °C

4: 99 percent / n-Bu₄N⁽¹⁺⁾*F^(1-) / tetrahydrofuran / 2 h / 23 °C

5: 87 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 2 h / 23 °C

6: 71 percent / tetrahydrofuran / 3 h / -78 °C

7: 62 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

8: 90 percent / Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / 14 h / 40 °C

9: NaOH / tetrahydrofuran; H₂O / 14 h / 0 °C

10: imidazole / dimethylformamide / 18 h / 23 °C

11: diethyl ether / 0.5 h / 0 °C

12: OsO₄; NMO / methanol; H₂O / 6 h / 23 °C

With 1H-imidazole; sodium hydroxide; osmium(VIII) oxide; lithium borohydride; N-methyl-2-indolinone; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; Grubbs catalyst first generation; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; 5: Dess-Martin oxidation / 6: Brown's allylboration;
DOI:10.1016/S0040-4039(03)00744-5