129312-27-2

Upstream product

• 13199-23-0 O²,O³;O⁵,O⁶-diisopropylidene-D-gulose 
• 6322-07-2 D-gulono-1,4-lactone 
• 67642-42-6 2,3,5,6-di-O-isopropylidene-D-gulono-1,4-lactone 
• 78039-08-4 2,3:5,6-di-O-isopropylidene-α-D-gulono-furanose 
• 14686-88-5 3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose 
• 26775-14-4 3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-gulofuranose 
• 14686-89-6 (1,2:5,6)-di-O-isopropylidene-D-gulose 
• 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 
• 260441-81-4 2,3:5,6-di-O-isopropylidene-D-gulose oxime 

Downstream Products

• 1370639-67-0 C₂₈H₄₃NO₉ 

Relevant academic research and scientific papers

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.

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.