104320-20-9

Upstream product

• 260441-81-4 2,3:5,6-di-O-isopropylidene-D-gulose oxime 
• 78039-08-4 2,3:5,6-di-O-isopropylidene-α-D-gulono-furanose 
• 6322-07-2 D-gulono-1,4-lactone 
• 7757-38-2 2,3,5,6-di-O-isopropylidene-D-mannofuranose 
• 78039-12-0 (3aR,4R,6S,6aR)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-furo[3,4-d][1,3]dioxol-4-ol 
• 14686-89-6 (1,2:5,6)-di-O-isopropylidene-D-gulose 
• 26775-14-4 3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-gulofuranose 
• 14686-88-5 3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose 
• 67642-42-6 2,3,5,6-di-O-isopropylidene-D-gulono-1,4-lactone 
• 13199-23-0 O²,O³;O⁵,O⁶-diisopropylidene-D-gulose 

Downstream Products

• 1370639-67-0 C₂₈H₄₃NO₉ 
• 497155-65-4 [cyclohexylmeth-(Z)-ylidene][(3aS,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]amine N-oxide 

Relevant academic research and scientific papers

ZnCl2-mediated stereoselective addition of terminal alkynes to D-(+)-mannofuranosyl nitrones

(Chemical Equation Presented) An optimized process for the addition of terminal alkynes to chiral nitrones using ZnCl2 and NEt3 in toluene is reported. The new reaction protocol is facile to perform and cost-effective. The resulting

Reversal of Stereoselectivity in Cycloadditions of Five-Membered Cyclic Nitrones Derived from Hexoses

Two five-membered cyclic nitrones derived from hexoses, a newly synthesized d-allo-configured nitrone and an already known d-talo-configured nitrone, have been examined in 1,3-dipolar cycloaddition reactions with vinyl acetate, allyl benzoate, methyl acrylate, acrylonitrile, and vinylene carbonate. The reactions of the d-allo-configured nitrone proceeded preferentially through the expected exo-anti transition state, but all the cycloadditions of the d-talo-configured nitrone surprisingly showed high exo-syn selectivity. This reversal of stereoselectivity has been explained by 3D analysis of the preferred conformations of the nitrones, obtained from X-ray data. The structures were further inspected using CONFLEX, PM5, and DFT calculations. All these methods revealed that the dioxolane substituents attached to C-5 of both nitrones had opposite spatial locations.

Enantioselective, chromatography-free synthesis of β3-Amino acids with natural and unnatural side chains

β3-Amino acids are key components of some pharmaceuticals, excellent surrogates for metabolically labile α-amino acids, and building blocks for chiral heterocycles. Unfortunately they are not easily accessible in enantiomerically pure form, especially when possessing unnatural side chains. A flexible, chromatography-free process for the synthesis of enantiopure β3-amino acids possessing natural and unnatural side chains is described. The procedure uses inexpensive starting materials and reagents and offers a good alternative to the hazardous and expensive Arndt-Eistert homologation of enantiopure α-amino acids. Its utility has been demonstrated with the preparative scale synthesis of two valuable β3-amino acids possessing unnatural side chains.

Enantioselective Synthesis of 5-LO Inhibitors Using a Gulofuranose Auxiliary

The pure R-(+)-enantiomer of 5-lipoxygenase inhibitor Zileuton was prepared by diastereoselective methyl Grignard addition to an aldonitrone bearing a D-gulofuranose-derived chiral auxiliary.Addition of the Lewis acid trimethylaluminum leads to a reversal of the alkylation stereochemistry and the potent pyrido analogue, R-(+)-RS-27871 was prepared in this way from an L-gulofuranose-derived nitrone.