203380-20-5

Basic information

• Product Name: (1S,2R,3S,4R)-3-methoxymethyl-2-triphenylstannylbicyclo[2.2.1]heptane(-)
• CAS NO: 203380-20-5
• Molecular Weight: 489.245
• Mol File: 203380-20-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1S,2R,3S,4R)-3-methoxymethyl-2-triphenylstannylbicyclo[2.2.1]heptane(-)(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R,3S,4R)-3-methoxymethyl-2-triphenylstannylbicyclo[2.2.1]heptane(-)(203380-20-5)
• EPA Substance Registry System: (1S,2R,3S,4R)-3-methoxymethyl-2-triphenylstannylbicyclo[2.2.1]heptane(-)(203380-20-5)

Safety Data

• Hazardous Substances Data: 203380-20-5(Hazardous Substances Data)

Upstream product

• 203380-23-8 (1S,2R,3S,4R)-3-hydroxymethyl-2-triphenylstannylbicyclo[2.2.1]heptane 
• 74-88-4 methyl iodide 

Downstream Products

• 203380-22-7 diphenyl[(1S,2R,3S,4R)-3-(1-methoxymethyl)bicyclo[2.2.1]heptan-2-yl]tin hydride 

Relevant articles and documents

Synthesis of chiral organotin reagents: Synthesis of diphenyl-{(1S,2R,3S,4R)-3-(alkoxymethyl)bicyclo[2.2.1]heptan-2-yl}tin hydrides. X-Ray crystal structure of (R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl (1S,2S,3R,4R)-3-triphenylstannylbicyclo[2.2.1]hept-5-ene-2-carboxylate

Conditions have been developed for the stereoselective Diels-Alder addition of cyclopentadiene to (R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl (E)-3-triphenylstannylprop-2-enoate 10 to give the endo-adduct 14 whose structure has been confirmed by X-ray crystallography. The adduct 14 is converted into (1S,2R,3S,4R)-3-hydroxymethylbicyclo[2.2.1]heptan-2-yl(triphenyl)stannane 22 which is shown to have an enantiomeric excess (ee) of 94%. This alcohol has been converted into its methyl ether (-)-3, trityl ether 25, tert-butyldimethylsilyl ether 26 and 1-naphthoate 27 which give the tin hydrides 4, 31-34 on treatment with iodine and sodium borohydride. Aspects of the chemistry of these enantiomerically enriched tin hydrides are briefly discussed.