107289-12-3

Upstream product

• 100017-18-3 (2R,6R)-2-tert-butyl-6-methyl-1,3-dioxan-4-one 
• 100-52-7 benzaldehyde 
• 630-19-3 pivalaldehyde 
• 107289-20-3 (2R)-2-(tert-butyl)-6-methyl-2H,4H-1,3-dioxin-4-one 

Downstream Products

• 129287-64-5 (2R,5R,6R)-2-tert-Butyl-6-methyl-5-((R)-1-phenyl-heptyl)-[1,3]dioxan-4-one 
• 129287-64-5 (1'S,2R,5R,6R)-2-tert-Butyl-6-methyl-5-(1'-phenylheptyl)-1,3-dioxan-4-on 
• 129287-63-4 (2R,5R,6R)-2-tert-Butyl-6-methyl-5-((R)-1-phenyl-pentyl)-[1,3]dioxan-4-one 
• 129287-63-4 (1'S,2R,5R,6R)-2-tert-Butyl-6-methyl-5-(1'-phenylpentyl)-1,3-dioxan-4-on 
• 129287-62-3 (2R,5R,6R)-2-tert-Butyl-6-methyl-5-((R)-1-phenyl-butyl)-[1,3]dioxan-4-one 
• 129287-62-3 (1'S,2R,5R,6R)-2-tert-Butyl-6-methyl-5-(1'-phenylbutyl)-1,3-dioxan-4-on 
• 129287-76-9 (2R,5S,6R)-5-Benzyl-2-tert-butyl-6-methyl-1,3-dioxan-4-on 
• 107289-11-2 (2R,5R,6R)-5-Benzyl-2-(tert-butyl)-6-methyl-1,3-dioxan-4-on 
• 118356-63-1 (E,2R,6R)-5-Benzyliden-2-tert-butyl-6-methyl-1,3-dioxan-4-on 
• 129287-49-6 (Z,2R,6R)-5-Benzyliden-2-tert-butyl-6-methyl-1,3-dioxan-4-on 
• 129287-65-6 (2R,5R,6R)-2-tert-Butyl-6-methyl-5-(1'-phenylbenzyl)-1,3-dioxan-4-on 
• 129287-80-5 (1'R,2R,3S)-2-(1'-Hydroxyethyl)-3-phenylheptansaeure 
• 129287-81-6 (2R,3R)-2-Diphenylmethyl-3-hydroxybutansaeure 
• 69657-31-4 (S)-3-Phenyl-heptanoic acid methyl ester 

Relevant academic research and scientific papers

A Simple Procedure for the Preparation of Chiral 'Tris(hydroxymethyl)methane' Derivatives

The aldol adducts 1a-13a of (R,R)-2-(tert-butyl)-6-methyl-1,3-dioxan-4-one (from 3-hydroxybutanoic acid) to aldehydes, single diastereoisomers obtained as described previously, are acetylated or benzoylated to the corresponding esters 1b-5b and 6c-13c, re

(E,R,R)-5-Alkylidene-2-tert-butyl-6-methyl-1,3-dioxan-4-ones: Preparation from (R)-3-Hydroxybutbutyric Acid, Cuprate Additions and Hydrolyses to 3-Hydroxycarboxylic Acids with Chiral Secondary Alkyl Substituents in the 2-Position

Li enolates of (R,R)-2-tert-Butyl-6-methyl-1,3-dioxan-4-one add to aliphatic or aromatic aldehydes with relative topicity Re,Re (2:1 to 10:1, 9 examples).The title compounds are obtained from these aldol adducts by dehydration through mesylates (5 example

123. 1,3-Dioxanone Derivatives from β-Hydroxy-carboxylic Acids and Pivalaldehyde. Versatile Buiding Blocks for Syntheses of Enantiomerically Pure Compounds. A Chiral Acetoacetic Acid Derivative

(R)-3-Hydroxybutyric acid (from the biopolymer PHB) and pivalaldehyde give the crystalline cis- or (R,R)-2-(tert-butyl)-6-methyl-1,3-dioxan-4-one (1a), the enolate of which is stable at low temperature in THF solution and can be alkylated diastereoselectively (->3, 4, 5, and 7).Phenylselenation and subsequent elimination give an enantiomerically pure enol acetal 10 of aceto-acetic acid.Some reactions of 10 have been carried out, such as Michael addition (->11), alkylation on the CH3 substituent (->13), hydrogenation of the C=C bond (->1a) and photochemical cycloaddition (->16).The overall reactions are substitutions on the one sterogenic center of the starting β-hydroxy acid without racemization and without using a chiral auxiliary.