340699-28-7

Upstream product

• 100-39-0 benzyl bromide 
• 114185-07-8 ethyl (2R)-2-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-2-hydroxyacetate 
• 874897-00-4 (S)-(2-Chloro-acetoxy)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetic acid ethyl ester 
• 92973-39-2 O³,O⁴-(1-methylethylidene)-L-threonic acid 
• 15042-01-0 5,6-O-isopropylidene-L-ascorbic acid 
• 340699-14-1 ethyl (2S,3S)-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate 

Downstream Products

• 100906-42-1 2-O-benzyl-3,4-O-isopropylidene-L-threose 
• 84379-53-3 2-O-benzyl-3,4-O-isopropylidene-L-threitol 
• 1061228-25-8 (4S,Z)-ethyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate 
• 874896-58-9 (4S,E)-ethyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate 
• 874896-66-9 (2R,3S,4R,5S)-2,3:5,6-di(O-isopropylidene)-4-O-benzyl-2,3,4,5,6-pentahydroxyhexanal 
• 874896-82-9 (2S,3S,4R,5S)-2,3:5,6-di(O-isopropylidene)-4-O-benzyl-2,3,4,5,6-pentahydroxyhexanal 
• 874896-83-0 (2R,3R,4R,5S)-2,3:5,6-di(O-isopropylidene)-4-O-benzyl-2,3,4,5,6-pentahydroxyhexanal 
• 874896-65-8 (2S,3R,4R,5S)-2,3:5,6-di(O-isopropylidene)-4-O-benzyl-2,3,4,5,6-pentahydroxyhexanal 
• 874896-78-3 methyl (2S,3R,4S,5S)-4-O-benzyl-5,6-O-isopropylidene-2,3,4,5,6-pentahydroxyhexanoate 
• 874896-79-4 methyl (2R,3S,4S,5S)-4-O-benzyl-5,6-O-isopropylidene-2,3,4,5,6-pentahydroxyhexanoate 
• 874896-62-5 (2R,3R,4S)-ethyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,3-dihydroxybutanoate 
• 874896-61-4 ethyl (2S,3S,4S,5S)-4-O-benzyl-5,6-O-isopropylidene-2,3,4,5,6-pentahydroxyhexanoate 
• 874896-80-7 methyl (2S,3S,4R,5S)-2,3:5,6-di(O-isopropylidene)-4-O-benzyl-2,3,4,5,6-pentahydroxyhexanoate 
• 874896-81-8 methyl (2R,3R,4R,5S)-2,3:5,6-di(O-isopropylidene)-4-O-benzyl-2,3,4,5,6-pentahydroxyhexanoate 

Relevant academic research and scientific papers

Synthesis of C1–C11 eribulin fragment and its diastereomeric analogues

A practical stereoselective synthesis of the central C1–C10 fragment of eribulin and its two diastereomeric analogues is developed. Our approach relied on the use of L-ascorbic acid as the starting material which allowed accessing a key intermediate with a syn diol moiety (C9 and C10 of eribulin) and a carboxylic ester group. A functionalized six membered lactone having several required hydroxyl groups was then obtained. In a number of steps, the lactone was converted to an intermediate for our key oxa-Michael reaction. A regio- and stereocontrolled intramolecular oxa-Michael reaction completed the synthesis of the C1–11 fragment having a trans-fused tetrahydropyrans with the exact stereochemistry of various hydroxyl groups, as in eribulin.

SUBSTITUTED BIARYL ALKYL AMIDES

Disclosed herein are substituted biaryl alkyl amide compounds, methods of synthesizing substituted biaryl alkyl amide compounds and methods of treating diseases and/or conditions with substituted biaryl alkyl amide compounds.

Diastereoselective synthesis of all eight L-hexoses from L-ascorbic acid

A novel versatile method for the synthesis of all eight diastereomerically pure L-hexoses was developed. L-Ascorbic acid was converted to two diastereomers A. These α-hydroxy esters were transformed into four γ-alkoxy- α,β-unsaturated esters C via the int

Stereoisomeric imidazolo-pentoses - Synthesis, chiroptical properties, and evaluation as glycosidase inhibitors

The syntheses of all four imidazolo-piperidino-pentoses in the L-series ent-2 to ent-5, and of three out of the four possible stereomers in the D-series 3, 4, and 5, are reported. The linear imidazolo sugar precursors were prepared, either by double condensation of formamidine with protected aldohexoses, or by nucleophilic addition of a lithiated imidazole derivative to protected aldotetroses. Cyclisation of these linear imidazolo-carbohydrates was performed by intramolecular SN2 reactions. These were followed by deprotection to the target molecules. The four pairs of opposite enantiomers showed pronounced mirror-image-type Cotton effects in their CD spectra. All stereomers of the D-series show a negative rotatory power ([α]D), while the stereomers of the L-series show a positive one. None of the eight imidazolo sugars inhibited the replication of HIV-1. Some of them proved to be rather selective but only moderately potent inhibitors of α-glycosidases, as determined by Michaelis-Menten kinetics.