(2R,3S,4R)-3-benzoyl-4-(tert-butyldimethylsiloxy)-2,3-(isopropylidenedioxy)pentanoic acid

Base Information

Chemical Name:(2R,3S,4R)-3-benzoyl-4-(tert-butyldimethylsiloxy)-2,3-(isopropylidenedioxy)pentanoic acid
CAS No.:1449306-98-2
Molecular Formula:C₂₁H₃₂O₆Si
Molecular Weight:408.567
Hs Code.:

Synonyms:(2R,3S,4R)-3-benzoyl-4-(tert-butyldimethylsiloxy)-2,3-(isopropylidenedioxy)pentanoic acid

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Chemical Property of (2R,3S,4R)-3-benzoyl-4-(tert-butyldimethylsiloxy)-2,3-(isopropylidenedioxy)pentanoic acid

Chemical Property:

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Technology Process of (2R,3S,4R)-3-benzoyl-4-(tert-butyldimethylsiloxy)-2,3-(isopropylidenedioxy)pentanoic acid

There total 6 articles about (2R,3S,4R)-3-benzoyl-4-(tert-butyldimethylsiloxy)-2,3-(isopropylidenedioxy)pentanoic acid 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: 78.0%

: 1449307-09-8
(2R,3S)-3-[(R)-1-(tert-butyldimethylsiloxy)ethyl]-2,3-(isopropylidenedioxy)-4-oxo-4-phenylbutanal

: 1449306-98-2
(2R,3S,4R)-3-benzoyl-4-(tert-butyldimethylsiloxy)-2,3-(isopropylidenedioxy)pentanoic acid

Guidance literature:: With sodium periodate; ruthenium(III) chloride monohydrate; In tetrachloromethane; water; acetonitrile; at 0 - 20 ℃; for 3.25h; Inert atmosphere;
DOI:10.1016/j.tet.2013.05.091

Reference yield:

: C₃₁H₅₂O₆Si

: 1449306-98-2
(2R,3S,4R)-3-benzoyl-4-(tert-butyldimethylsiloxy)-2,3-(isopropylidenedioxy)pentanoic acid

Guidance literature:: Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / 1.5 h / 20 °C / Inert atmosphere

2: sodium periodate; ruthenium(III) chloride monohydrate / acetonitrile; tetrachloromethane; water / 3.25 h / 0 - 20 °C / Inert atmosphere

With sodium periodate; ruthenium(III) chloride monohydrate; toluene-4-sulfonic acid; In tetrachloromethane; water; acetonitrile;
DOI:10.1016/j.tet.2013.05.091

Reference yield:

: 1449306-99-3
(3S,4R,5R)-3-[(R)-1-hydroxyethyl]-5-{(1R,2S,5R)-[2-isopropyl-5-methylcyclohexyl]oxy}-3,4-(isopropylidenedioxy)-4,5-dihydro-3H-furan-2-one

: 1449306-98-2
(2R,3S,4R)-3-benzoyl-4-(tert-butyldimethylsiloxy)-2,3-(isopropylidenedioxy)pentanoic acid

Guidance literature:: Multi-step reaction with 4 steps

1: triethylamine / dichloromethane / 2.5 h / 0 - 20 °C / Inert atmosphere

2: lithium chloride / tetrahydrofuran; dibutyl ether / 0.17 h / -10 °C / Inert atmosphere

3: toluene-4-sulfonic acid / 1.5 h / 20 °C / Inert atmosphere

4: sodium periodate; ruthenium(III) chloride monohydrate / acetonitrile; tetrachloromethane; water / 3.25 h / 0 - 20 °C / Inert atmosphere

With sodium periodate; ruthenium(III) chloride monohydrate; toluene-4-sulfonic acid; triethylamine; lithium chloride; In tetrahydrofuran; tetrachloromethane; dichloromethane; dibutyl ether; water; acetonitrile;
DOI:10.1016/j.tet.2013.05.091