1428980-17-9

Upstream product

• 1428980-02-2 methyl 2,3-di-O-(tert-butyldimethylsilyl)-6-deoxy-4-O-((2R)-2-((1,3-dioxolan-2-yl)methyl)-2-methyl-3-butenoyl)-α-D-glucopyranoside 
• 1428980-01-1 methyl 2,3-di-O-(tert-butyldimethylsilyl)-6-deoxy-4-O-((2R)-2-(1,3-dioxolan-2-yl)methyl-2-formylpropanoyl)-α-D-glucopyranoside 
• 1428980-00-0 methyl 2,3-di-O-(tert-butyldimethylsilyl)-6-deoxy-4-O-((2R)-2-(1,3-dioxolan-2-yl)methyl-2-(ethoxycarbonyl)propanoyl)-α-D-glucopyranoside 
• 1428979-98-9 methyl 2,3-di-O-(tert-butyldimethylsilyl)-6-deoxy-4-O-((2R)-2-ethoxycarbonyl-2-formylmethylpropanoyl)-α-D-glucopyranoside 
• 1428979-96-7 methyl 2,3-di-O-(tert-butyldimethylsilyl)-6-deoxy-4-O-((2R)-2-ethoxycarbonyl-2-methylpent-4-enoyl)-α-D-glucopyranoside 
• 114694-29-0 (R)-3-hydroxy-2,3-dimethylbutyl 4-methylbenzenesulfonate 
• 73295-16-6 (R)-2,3-dimethyl-1,3-butanediol 
• 1428980-14-6 (1S,2R,5R)-2-((1,3-dioxolan-2-yl)methyl)-1(2-(ethoxycarbonyl)ethynyl)-2,4,5-trimethylcyclohex-3-en-1-ol 
• 1428980-13-5 (2R,5R)-2-((1,3-dioxolan-2-yl)methyl)-2,4,5-trimethylcycohex-3-en-1-one 
• 623-47-2 propynoic acid ethyl ester 
• 1428980-12-4 (3R,6R)-3-[(1,3-dioxolan-2-yl)methyl]-3,6,7-trimethylocta-1,7-dien-4-one 
• 1428980-09-9 (2R)-2-((1,3-dioxolan-2-yl)methyl)-2-methylbut-3-enal 
• 1428980-08-8 (3S)-4-bromo-2,3-dimethylbut-1-ene 
• 1428980-05-5 (S)-2,3-dimethylbut-3-en-1-yl 4-methylbenzenesulfonate 

Relevant academic research and scientific papers

Synthetic studies of the spirocyclic cyclohexene part of versipelostatin, a novel GRP78/Bip molecular chaperone downregulator

The spirocyclic part consisting of an -acylated tetronic acid and a multisubstituted cyclohexene embedded in versipelostatin, a novel GRP78/Bip molecular chaperone downregulator, has been synthesized in enantiomerically pure form. The asymmetric synthesis of the targeted spiro4.5-1-oxa-7-decen-2,4-dione derivative was characterized by (1) stereoselective allylation at the -carbon of methylmalonate diester, in which one carboxylic acid was esterified with a D-glucose-derived chiral template, (2) construction of the tetrasubstituted cyclohexenone substructure by high-yielding ring-closing metathesis and (3) stereoselective construction of the spirocyclic tetronic acid part starting from the cyclohexenone obtained as the ring-closing metathesis product.