89543-99-7

Upstream product

• 83968-02-9 2,2-dimethyl-4-vinyl-1,3-dioxolane 
• 698-16-8 benzohydroximoyl chloride 
• 89543-87-3 1-(3-phenyl-isoxazolin-5-yl)ethane-1,2-diol 
• 77-76-9 2,2-dimethoxy-propane 
• 119496-37-6 (tert-Butyl-dimethyl-silanyloxy)-(3-phenyl-4,5-dihydro-isoxazol-5-yl)-acetaldehyde 
• 119496-13-8 5-[1-(tert-Butyl-dimethyl-silanyloxy)-2,2-bis-tert-butylsulfanyl-ethyl]-3-phenyl-4,5-dihydro-isoxazole 
• 92287-44-0 3-phenyl-5-vinyl-4,5-dihydroisoxazole 
• 67-64-1 acetone 

Downstream Products

• 93106-31-1 ribo-5-amino-5-phenyl-1,2,3-pentanetriol 1,2-acetonide 
• 93106-31-1 arabino-5-amino-5-phenyl-1,2,3-pentanetriol 1,2-acetonide 
• 93106-31-1 (1S,3S)-3-Amino-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-phenyl-propan-1-ol 
• 93106-31-1 (1S,3R)-3-Amino-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-phenyl-propan-1-ol 

Relevant academic research and scientific papers

Stereoselective Synthesis of Masked Amino-polyols via Osmylation of 4,5-Dihydro-5-vinylisoxazoles

Variously substituted 4,5-dihydro-5-vinylisoxazoles, obtained by regio- and stereospecific cycloaddition of nitrile oxides to dienes, undergo smooth OsO4-catalyzed cis-hydroxylation to give amino-polyol precursors.The reaction is 'anti'-selective, the dia

DIASTEREOSELECTIVE NITRILE OXIDE CYCLOADDITIONS TO CHIRAL ALLYL ETHERS DERIVED FROM 1,1-DITHIO-3-BUTEN-2-OLS.

Highly diastereoselective cycloaddition of nitrile oxides to the title compounds gives masked polyfunctional products amenable to a variety of synthetic elaboration; an entry to enantiomerically pure derivatives is described.

Stereoselective Osmylation of 5-Vinyl-4,5-dihydroisoxazoles

Osmium tetroxide-catalysed cis-hydroxylation of 5-vinyl-4,5-dihydroisoxazoles proceeds stereoselectively affording the anti-products in fair to excellent diastereoisomeric excess; an entry to optically active compounds is also described.

SYNTHESIS OF AMINO SUGARS VIA ISOXAZOLINES. DL- AND D-LIVIDOSAMINE (2-AMINO-2,3-DIDEOXY-RIBO-HEXOSE) DERIVATIVES FROM 4-VINYL-1,3-DIOXOLANES AND NITROACETALDEHYDE ACETALS

1,3-Dipolar cycloaddition of nitrile oxides, generated from nitroethanol and nitroacetaldehyde derivatives 3, 21 and 22, respectively, and of benzonitrile oxide to 4-vinyldioxolanes 1,2 gave ca 4:1 erythro/threo mixtures of corresponding isoxazolines.LAH reduction of erytho isoxazolines proceeded with similar (ca4:1) selectivity to furnish protected ribo-amino-polyols 11, 15, 19, DL- and D-lividosamines 31 and 33, respectively, as main products.The DL-lividosamine derivative 33 was obtained pure by crystallization.In the D-series, the corresponding ribo/arabino mixture D-31/D-32 was transformed to the known α-methyl D-lividosaminide D-37.