216769-26-5

Basic information

• Product Name: 2H-Pyran-2-one, 6-[(4S,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]tetrahydro-, (6R)-
• CAS NO: 216769-26-5
• Molecular Formula: C16H20O4
• Molecular Weight: 276.332
• Mol File: 216769-26-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2H-Pyran-2-one, 6-[(4S,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]tetrahydro-, (6R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Pyran-2-one, 6-[(4S,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]tetrahydro-, (6R)-(216769-26-5)
• EPA Substance Registry System: 2H-Pyran-2-one, 6-[(4S,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]tetrahydro-, (6R)-(216769-26-5)

Safety Data

• Hazardous Substances Data: 216769-26-5(Hazardous Substances Data)

Upstream product

• 1152589-47-3 (R)-2-[(4S,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]cyclopenatanone 
• 216769-09-4 (2R,2'R,6'R)-2-hydroxy-2-(6'-tert-butyldiphenylsilanyloxymethylpyranyl)-1-phenylethanone 
• 216769-13-0 (2S,2'R,6'R)-2-hydroxy-2-(6'-tert-butyldiphenylsilanyloxymethylpyranyl)-1-phenylethanone 
• 891491-87-5 Z-(2R,2'R)-trimethyl-[1-phenyl-2-(6'-tert-butyldiphenylsilanyloxymethylpyran-2'-yloxy)-vinyloxy]-silane 
• 216769-17-4 (4R,5S,2'R,6'R)-2,2-dimethyl-5-(6'-tert-butyldiphenylsilanyloxymethylpyran-2'-yl)-4-phenyl-[1,3]dioxolane 
• 891491-88-6 (1R,2R)-1-[(2R,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-2-phenyl-ethane-1,2-diol 
• 216769-40-3 (R,R)-N-methoxy-N-methyl-2-(6'-tert-butyldiphenylsilanyloxymethylpyranyloxy)-acetamide 
• 216769-05-0 (R,R)-2-(6'-tert-butyldiphenylsilanyloxymethylpyranyloxy)-1-phenylethanone 
• 216769-01-6 (R)-6-(tert-butyldiphenylsilanyloxymethyl)-tetrahydropyran-2-ol 
• 216769-55-0 (6R,4'S,5'R) 6-(2',2'-dimethyl-5'-phenyl-[1',3']dioxolan-4'-yl)-pyranyl acetate 
• 216769-22-1 (2R,6R)-6-((4S,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-tetrahydro-pyran-2-carboxylic acid 
• 216769-45-8 (4R,5S,2'R,6'R)-2,2-dimethyl-5-(6'-hydroxymethylpyran-2'-yl)-4-phenyl-[1,3]dioxolane 
• 216769-50-5 (2R,6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1,3]dioxolan-4'-yl)-pyran-2-carbaldehyde 
• 216769-61-8 (R)-6-((4S,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-tetrahydro-pyran-2-ol 

Downstream Products

• 146236-73-9 (+)-goniodiol 
• 163630-06-6 (6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1',3']dioxolan-4'-yl)-5,6-dihydropyran-2-one 
• 891491-89-7 (6R,4'S,5'R)-6-(2',2'-dimethyl-5'-phenyl-[1',3']dioxolan-4'-yl)-3-phenylselanyltetrahydropyran-2-one 

Relevant articles and documents

Syntheses of all stereoisomers of goniodiol from yeast-reduction products and their antimicrobiological activity

All stereoisomers of goniodiol were synthesized from yeast-reduction products. The C-6 chiral centers were converted from the chiral centers of the yeast-reduction products. Stereoselective conversion of the alkene, which had been prepared from the yeast-reduction product, to glycol constructed the C-7 and C-8 stereochemistry. (+)-Goniodiol and 7-epi-(+)-goniodiol showed the highest antibacterial activity (MIC, 3.1 mM) against Yersinia intermedia.

A total synthesis of (+)-Goniodiol using an anomeric oxygen-to-carbon rearrangement

A new route to (+)-Goniodiol 1, a potent and selective cytotoxin, is described, using a diastereoselective oxygen-to-carbon rearrangement of an anomerically linked silyl enol ether as the key step.