334784-69-9

Basic information

• Product Name: (2R,3S)-3-O-tert-butyldiphenylsilyl-4-pentene-1,2,3-triol
• Synonyms: (2R,3S)-3-O-tert-butyldiphenylsilyl-4-pentene-1,2,3-triol
• CAS NO: 334784-69-9
• Molecular Weight: 356.537
• Mol File: 334784-69-9.mol

Chemical Properties

• CAS DataBase Reference: (2R,3S)-3-O-tert-butyldiphenylsilyl-4-pentene-1,2,3-triol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-3-O-tert-butyldiphenylsilyl-4-pentene-1,2,3-triol(334784-69-9)
• EPA Substance Registry System: (2R,3S)-3-O-tert-butyldiphenylsilyl-4-pentene-1,2,3-triol(334784-69-9)

Safety Data

• Hazardous Substances Data: 334784-69-9(Hazardous Substances Data)

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 212579-64-1 (4R)-1-(2,2-dimethyl-[1,3]dioxolan-4-yl)allyl alcohol 
• 223558-55-2 (2R,3S)-3-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-4-pentene-1,2,3-triol 

Relevant articles and documents

Stereoselective synthesis of (3S,8R,9R,10R)-heptadeca-1-ene-4,6-diyne tetrol and its 3-epimer from D-mannitol

(3S,8R,9R,10R)-Heptadeca-1-ene-4,6-diyne tetrol and its 3-epimer were synthesized, and it was found that the relative configuration which was proposed for 1 was incorrect. Georg Thieme Verlag Stuttgart.

Synthesis of substituted tetrahydrofuran by electrophile-induced cyclization of 4-pentene-1,2,3-triols - An example of 5-exo versus 5-endo cyclization governed by the electrophile

Differently protected 4-pentene-1,2,3-triols 5-8 were obtained from glyceraldehyde and submitted to iodine-based electrophile-induced cyclization to give tetrahydrofuran derivatives 10 and 18, with high chemo-, regio-, and stereo-selectivity, through a 5-exo cyclization process. However, when an electrophilic selenium reagent was treated with similar alkene triols 5, 7, and 8, the product depended on the protecting group at the primary hydroxy moiety. Thus, while compounds 5a and 5b, unprotected at the primary hydroxy group, give compounds 26 and 27, and 32 and 33, respectively, through a 5-exo cyclization process, compounds 7 and 8, protected at the primary hydroxy group, give the 5-endo cyclization products 22-25 and 28-31 in good yields. The electrophile-induced cyclization of 4-pentene-1,2,3-triols to give tetrahydrofuran derivatives can be directed towards a 5-exo process by the use of iodine or, when the primary hydroxy group is unprotected, selenium. When the primary hydroxy group is protected, use of selenium results in 5-endo cyclization.