817201-03-9

Basic information

• Product Name: (2S,3S,4S,5R)-3-(tert-butyldiphenylsilyloxy)methyl-4-methyl-2,5-di(2-propenyl)-4-methyltetrahydrofuran
• Synonyms: (2S,3S,4S,5R)-3-(tert-butyldiphenylsilyloxy)methyl-4-methyl-2,5-di(2-propenyl)-4-methyltetrahydrofuran
• CAS NO: 817201-03-9
• Molecular Weight: 434.694
• Mol File: 817201-03-9.mol

Chemical Properties

• CAS DataBase Reference: (2S,3S,4S,5R)-3-(tert-butyldiphenylsilyloxy)methyl-4-methyl-2,5-di(2-propenyl)-4-methyltetrahydrofuran(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,4S,5R)-3-(tert-butyldiphenylsilyloxy)methyl-4-methyl-2,5-di(2-propenyl)-4-methyltetrahydrofuran(817201-03-9)
• EPA Substance Registry System: (2S,3S,4S,5R)-3-(tert-butyldiphenylsilyloxy)methyl-4-methyl-2,5-di(2-propenyl)-4-methyltetrahydrofuran(817201-03-9)

Safety Data

• Hazardous Substances Data: 817201-03-9(Hazardous Substances Data)

Upstream product

• 817201-16-4 (2R,3S,4S,5S)-3-(tert-butyldiphenylsilyloxy)methyl-4-methyl-2,5-bis(iodomethyl)-4-methyltetrahydrofuran 
• 1826-67-1 vinyl magnesium bromide 
• 817201-42-6 (2R,3S,4S,5S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methyl-tetrahydro-furan-2,5-dicarbaldehyde 
• 816455-25-1 (1S,2S,3R,4R)-2-(tert-butyldiphenylsilyloxy)methyl-3-hydroxymethyl-7-oxabicyclo[2.2.1]hept-5-ene 
• 817201-14-2 (2R,3S,4S,5S)-3-(tert-butyldiphenylsilyloxy)methyl-2,5-bis(hydroxymethyl)-4-methyltetrahydrofuran 
• 817201-13-1 (1R,2S,3S,4S,5R,6S)-2-(tert-butyldiphenylsilyloxy)methyl-5,6-dihydroxy-3-methyl-7-oxabicyclo[2.2.1]heptane 
• 6118-51-0 exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride 
• 106137-27-3 exo-2,3-bis(hydroxymethyl)-7-oxabicyclo[2.2.1]hept-5-ene 
• 142507-59-3 (-)-7-oxabicyclo<2.2.1>hept-5-ene-exo-2,exo-3-dimethanol monoacetate 
• 142507-54-8 (1S,2S,3R,4R)-2-acetoxymethyl-3-hydroxymethyl-7-oxabicyclo[2.2.1]hept-5-ene 
• 142438-51-5 (1R*,2R*,3S*,4S*)-7-oxabicyclo[2.2.1]hept-5-ene-2,3-diylbis(methylene) diacetate 
• 817201-15-3 (2R,3S,4S,5S)-3-(tert-butyldiphenylsilyloxy)methyl-4-methyl-2,5-bis[(p-toluenesulfonyloxy)methyl]-4-methyltetrahydrofuran 
• 817201-09-5 (1S,2S,3R,4R)-2-(tert-butyldiphenylsilyloxy)methyl-3-(1-ethoxyethoxy)methyl-7-oxabicyclo[2.2.1]hept-5-ene 
• 817201-07-3 (1S,2S,3R,4R)-2-acetoxymethyl-3-(1-ethoxyethoxy)methyl-7-oxabicyclo[2.2.1]hept-5-ene 

Downstream Products

• 817201-17-5 (1R,6S,7S,8R)-3,4-dibromo-7-(tert-butyldiphenylsilyloxy)methyl-8-methyl-9-oxabicyclo[4.2.1]nonane 
• 817201-18-6 (1R,6S,7S,8R)-7-(tert-butyldiphenylsilyloxy)methyl-8-methyl-9-oxabicyclo[4.2.1]nona-2,4-diene 
• 817201-27-7 (1R,6S,7R,8S)-7-(furan-2-carbonyl)-8-methyl-9-oxabicyclo[4.2.1]nona-2,4-diene 
• 817201-02-8 (1R,6S,7S,8R)-7-(tert-butyldiphenylsilyloxy)methyl-8-methyl-9-oxabicyclo[4.2.1]non-3-ene 

Relevant articles and documents

Asymmetric total syntheses of (+)-mycoepoxydiene and related natural product (-)-1893A: Application of one-pot ring-opening/cross/ring-closing metathesis to construct their 9-oxabicyclo[4.2.1]nona-2,4-diene skeleton

The total syntheses of (+)-mycoepoxydiene and (-)-1893A have been completed. The present synthetic strategy features the use of one-pot ring-opening/cross metathesis (ROM/CM) followed by a ring-closing metathesis (RCM) reaction, allowing for the concise construction of the 9-oxabicyclo-[4.2.1]nona-2,4-diene framework from a 7-oxabicyclo[2.2.1]hept-2- ene derivative and 1,3-butadiene. The sequential metathesis product was converted into (+)-mycoepoxydiene through the oxidative rearrangement of a furfuryl alcohol to a pyranone, thereby establishing its absolute stereochemistry. From the common intermediate, a structurally related natural product (-)-1893A was also synthesized via the vinylogous aldol reaction.