227792-06-5

Basic information

• Product Name: (2S,3S,4S)-(+)-1-<(tert-butyldiphenylsilyl)oxy>-2,4-dimethyl-5-hexyn-3-ol
• Synonyms: (2S,3S,4S)-(+)-1-<(tert-butyldiphenylsilyl)oxy>-2,4-dimethyl-5-hexyn-3-ol
• CAS NO: 227792-06-5
• Molecular Weight: 380.602
• Mol File: 227792-06-5.mol

Chemical Properties

• CAS DataBase Reference: (2S,3S,4S)-(+)-1-<(tert-butyldiphenylsilyl)oxy>-2,4-dimethyl-5-hexyn-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,4S)-(+)-1-<(tert-butyldiphenylsilyl)oxy>-2,4-dimethyl-5-hexyn-3-ol(227792-06-5)
• EPA Substance Registry System: (2S,3S,4S)-(+)-1-<(tert-butyldiphenylsilyl)oxy>-2,4-dimethyl-5-hexyn-3-ol(227792-06-5)

Safety Data

• Hazardous Substances Data: 227792-06-5(Hazardous Substances Data)

Upstream product

• 92817-88-4 (2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal 
• 121887-95-4 (R)-(+)-3-butyn-2-ol methanesulfonate 

Downstream Products

• 235099-40-8 (Z)-(4S,5S,6R)-7-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-4,6-dimethyl-hept-2-enoic acid 
• 235099-37-3 (Z)-(4S,5S,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-4,6-dimethyl-hept-2-enoic acid 
• 235099-38-4 (5S,6S)-6-{(1S)-2-[(tert-butyldiphenylsilyl)oxy]-1-methylethyl}-5-methyl-5,6-dihydro-2H-pyran-2-one 
• 142592-68-5 (5S,6S)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-5-methyl-5,6-dihydro-pyran-2-one 
• 235099-36-2 (4S,5S,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-4,6-dimethyl-hept-2-ynoic acid 

Relevant articles and documents

Addition of allenylzinc reagents, prepared in situ from nonracemic propargylic mesylates, to aldehydes. A new synthesis of highly enantioenriched homopropargylic alcohols

Enantioenriched propargylic mesylates are converted to chiral allenylzinc reagents via transient allenylpalladium species by treatment with a Pd(0)-phosphine catalyst in the presence of excess Et2Zn. These zinc reagents undergo S(E)2' additions to various aldehydes to yield mainly the anti homopropargylic alcohol adducts of high ee. The reaction is most efficient in THF with Pd(OAc)2· PPh3 as the catalyst precursor. As little as 2.5 mol % of this precursor is effective.