923986-89-4

Basic information

• Product Name: (1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-[(R)-1-phenyl-1-hydroxy-ethyl]-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.^9,11.0^2,17.0^8,13]-docosane
• Synonyms: (1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-[(R)-1-phenyl-1-hydroxy-ethyl]-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.^9,11.0^2,17.0^8,13]-docosane
• CAS NO: 923986-89-4
• Molecular Weight: 516.81
• Mol File: 923986-89-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-[(R)-1-phenyl-1-hydroxy-ethyl]-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.^9,11.0^2,17.0^8,13]-docosane(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-[(R)-1-phenyl-1-hydroxy-ethyl]-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.^9,11.0^2,17.0^8,13]-docosane(923986-89-4)
• EPA Substance Registry System: (1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-[(R)-1-phenyl-1-hydroxy-ethyl]-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.^9,11.0^2,17.0^8,13]-docosane(923986-89-4)

Safety Data

• Hazardous Substances Data: 923986-89-4(Hazardous Substances Data)

Upstream product

• 923986-87-2 (1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-benzoyl-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.^9,11.0^2,17.0^8,13]-docosane 
• 917-54-4 methyllithium 
• 75-16-1 methylmagnesium bromide 
• 923986-88-3 2,2-bis[(1S,2R,3S,5R)-2-hydroxymethyl-6,6-dimethylbicyclo[3.1.1]hept-3-ylsulfanyl]-1-phenylethanone 
• 444308-38-7 {(1S,2R,3S,5R)-3-mercapto-6,6-dimethylbicyclo[3.1.1]heptan-2-yl}methanol 

Downstream Products

• 923986-93-0 2,2-bis[(1S,2R,3S,5R)-2-(tert-butyl-dimethylsilanyloxymethyl)-6,6-dimethylbicyclo[3.1.1]hept-3-ylsulfanyl]-1-phenylethanone 
• 923986-95-2 (1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-[(R)-1,2-diphenyl-1-hydroxy-ethyl]-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.^9,11.0^2,17.0^8,13]-docosane 
• 923986-97-4 (1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-[(R)-1-phenyl-1-hydroxy-2-propenyl]-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.^9,11.0^2,17.0^8,13]-docosane 
• 923986-87-2 (1S,2R,8R,9S,11R,13S,17S,19R)-4,6-dioxa-14,16-dithia-15-benzoyl-10,10,20,20-tetramethylpentacyclo-[17.1.1.1.^9,11.0^2,17.0^8,13]-docosane 
• 923986-88-3 2,2-bis[(1S,2R,3S,5R)-2-hydroxymethyl-6,6-dimethylbicyclo[3.1.1]hept-3-ylsulfanyl]-1-phenylethanone 
• 2406-22-6 (R)-1-phenyl-1,2-ethanediol 
• 444308-38-7 {(1S,2R,3S,5R)-3-mercapto-6,6-dimethylbicyclo[3.1.1]heptan-2-yl}methanol 
• 4361-50-6 (R)-2-hydroxy-2-phenylpropanaldehyde 

Relevant articles and documents

Synthesis of a new (1R)-(-)-myrtenal-derived dioxadithiadodecacycle and its use as an efficient chiral auxiliary

(Chemical Equation Presented) The new macrocycle 9 (>70% yield from hydroxythiol 10) was treated with several nucleophilic reagents (RMgX, RLi, and LiAlH4) affording carbinols 12a-j (80-96% yield, >99:1 dr). Oxidative hydrolysis of 12a,c,e, followed by LiAlH4 reduction of the resulting mixture, gave 16a,c,e in >95% ee,16c being a key precursor for the preparation of fungicide 17. The absolute configuration of 9 and 12j (Nu = H) was established by single-crystal X-ray diffraction analyses and chemical correlation.