126946-53-0

Upstream product

• 15042-01-0 5,6-O-isopropylidene-L-ascorbic acid 
• 114185-07-8 ethyl (2R)-2-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-2-hydroxyacetate 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 5754-34-7 2-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol 
• 128112-01-6 (2R,3S)-2-<2-O-benzyl-3,4-O-isopropylidene-2,3,4-trihydroxybut-1-yl>-1,3-dithiane 
• 128057-04-5 (3R,4S)-3-O-benzyl-4,5-O-isopropylidene-3,4,5-trihydroxypentanal 
• 74134-78-4 (2S,3R)-3,4-epoxy-1,2-O-isopropylidenebutane-1,2-diol 
• 128056-99-5 (S)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl 4-methylbenzenesulfonate 

Relevant academic research and scientific papers

Syntheses of L-threose and D-erythrose analogues modified at position 2

2-O-Methyl-D-erythrose, 2-O-methyl-L-threose, 2-deoxy-D- and L- erythrose, and the corresponding acetonides have been prepared from the commercially available D-isoascorbic and L-ascorbic acids. The proportion of cyclic (α and β furanoses) and acyclic (aldehyde and hydrate) forms was determined in aqueous (D2O) solution by 1H and 13C NMR spectroscopy.

Total synthesis of phorboxazole A via de novo oxazole formation: Strategy and component assembly

The phorboxazole natural products are among the most potent inhibitors of cancer cell division, but they are essentially unavailable from natural sources at present. Laboratory syntheses based upon tri-component fragment coupling strategies have been developed that provide phorboxazole A and analogues in a reliable manner and with unprecedented efficiency. This has been orchestrated to occur via the sequential or simultaneous formation of both of the natural product's oxazole moieties from two serine-derived amides, involving oxidation-cyclodehydrations. The optimized preparation of three pre-assembled components, representing carbons 3-17, 18-30, and 31-46, has been developed. This article details the design and syntheses of these three essential building blocks. The convergent coupling approach is designed to facilitate the incorporation of structural changes within each component to generate unnatural analogues, targeting those with enhanced therapeutic potential and efficacy.

THE CHEMISTRYL OF L-ASCORBIC AND D-ISOASCORBIC ACIDS. 3: EFFICIENT SYNTHESES OF PURE R- AND S-1,2-O-ISOPROPYLIDENE-1,2,4-BUTANETRIOLS

Both enantiomers of 1,2-O-isopropylidene-1,2,4-butanetriol were prepared by two different and simple methods starting from readily available L-ascorbic and D-isoascorbic acids.