95598-71-3

Upstream product

• 613-90-1 benzoyl cyanide 
• 32233-43-5 2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol 
• 42890-76-6 (S)-1,2,4-butanetriol 
• 98-88-4 benzoyl chloride 
• 67-64-1 acetone 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 328381-97-1 (S)-3,4-bis((tert-butyldimethylsilyl)oxy)butyl benzoate 
• 95598-73-5 9-(S)-(4-Benzoyloxy-2-tetrahydropyranyloxybutyl)adenine 
• 95598-72-4 (2S)-4-O-Benzoyl-1-O-p-toluenesulfonylbutane-1,2,4-triol 
• 94992-56-0 (S)-1,2-O-isopropylidene-4-O-<(4-methylphenyl)sulfonyl>-1,2,4-butanetriol 
• 32233-43-5 2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol 

Relevant academic research and scientific papers

Synthesis of sialic acid derivatives based on chiral substrate-controlled stereoselective aldol reactions using pyruvic acid oxabicyclo[2.2.2]octyl orthoester

The synthesis of sialic acids and their analogs was accomplished based on substrate-controlled asymmetric aldol reactions between sterically complicated aldehydes easily prepared from commercially available carbohydrates and a novel pyruvic acid oxabicyclo[2.2.2]octyl orthoester. Systematic aldol reaction studies using chiral aldehydes revealed that α,β,γ-benzyloxy-substituted aldehydes with an α,β-anti relative configuration preferentially provided the Felkin products with the 4,5-anti configuration with high diastereoselectivity. The relative β,γ-configuration in α,β,γ-benzyloxy-substituted aldehydes with an α,β-syn arrangement exerted a secondary effect on the diastereoselectivity of the stereogenic center formed in aldol reactions, and α,β-syn-β,γ-anti benzyloxyaldehyde exhibited superior diastereoselectivity to α,β-syn-β,γ-syn benzyloxyaldehyde to yield the Felkin products.

Asymmetric 1,3-dipolar cycloaddition of nitrones with an electron-withdrawing group to allylic alcohols utilizing diisopropyl tartrate as a chiral auxiliary

The asymmetric 1,3-dipolar cycloaddition of nitrones possessing an electron-withdrawing group to allylic alcohols was achieved by the use of diisopropyl (R,R)-tartrate as a chiral auxiliary to afford the corresponding isoxazolidines with high regio-, diastereo-, and enantioselectivity. In the case of nitrones possessing an electron-withdrawing cyano or t-butoxycarbonyl group, 1,3-dipolar cycloaddition to 2-propen-1-ol occurred to produce the corresponding 3,5-trans-isoxazolidines with high enantioselectivity. To the contrary, nitrones possessing an amide moiety afforded the corresponding optically active 3,5-cis-isoxazolidines with completely opposite diastereoselectivity. A catalytic asymmetric 1,3-dipolar cycloaddition of nitrones possessing the N,N-diisopropylamide moiety to allylic alcohols was achieved to afford di- or trisubstituted isoxazolidines with excellent enantioselectivity of up to over 99% ee. The present asymmetric 1,3-dipolar cycloaddition was applied to the synthesis for the (2S,4R)-4-hydroxyornithine derivative.

Enantio- and diastereoselective synthesis of isoxazolidines by asymmetric 1,3-dipolar cycloaddition of nitrones

The asymmetric 1,3-dipolar cycloaddition of nitrones possessing electron withdrawing group to an achiral allyl alcohol was achieved by the use of diisopropyl (R,R)-tartrate as a chiral auxiliary to afford the corresponding isoxazolidines with high regio-, diastereo- and enantioselectivity.

Synthesis of 2-hydroxymethyl-1-oxaquinolizidine

The synthesis of 2-hydroxymethyl-1-oxaquinolizidine from L-malic acid and 1,5 pentanediol, is reported.

PREPARATION AND SYNTHETIC UTILIZATION OF 3-(ADENIN-9-YL)-2-HYDROXYALKANOIC ACIDS AND THEIR DERIVATIVES

Condensation of adenine and its substituted derivatives with 1,1-dialkoxy-2-bromoalkanes afforded substituted 2-(adenin-9-yl)-1,1-dialkoxyalkanes I and IV.Acid hydrolysis of I or IV, followed by reaction with alkali metal cyanides and acid hydrolysis, gave substituted 3-(adenin-9-yl)-2-hydroxyalkanoic acids II, V and VI.Methyl esters of these compounds (VIII) were converted into 3-(adenin-9-yl)alkane-1,2-diols IX by reduction with sodium borohydride. 3-(Adenin-9-yl)-2-methoxypropanoic acid (XVII) was obtained by oxidation of 9-(3-hydroxy-2-methoxypropyl)adenine (XVI)with sodium periodate; 4-(adenin-9-yl)-2-(S)-hydroxybutanoic acid (XXVII) was synthesized by oxidation of 9-(S)-(2-tetrahydropyranyloxy-4-hydroxybutyl)adenine (XXV), prepared from diethyl L-malate.Acid hydrolysis of XXV afforded 9-(S)-(2,4-dihydroxybutyl)adenine (XXVI). 4-(Adenin-9-yl)-3-hydroxypentanoic acid (XXIX) was obtained by reaction of malonic acid with 2-(adenin-9-yl)-1,1-diethoxypropane (IVa) in water.