114418-33-6

Basic information

• Product Name: (2S,3S)-2-benzyloxy-3-pentanol
• Synonyms: (2S,3S)-2-benzyloxy-3-pentanol
• CAS NO: 114418-33-6
• Molecular Weight: 194.274
• Mol File: 114418-33-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (2S,3S)-2-benzyloxy-3-pentanol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-2-benzyloxy-3-pentanol(114418-33-6)
• EPA Substance Registry System: (2S,3S)-2-benzyloxy-3-pentanol(114418-33-6)

Safety Data

• Hazardous Substances Data: 114418-33-6(Hazardous Substances Data)

Upstream product

• 53346-05-7 2-(benzyloxy)propanal 
• 78-00-2 tetraethyllead(IV) 
• 140654-13-3 (2S,3S,4R)-2-Benzyloxy-4-iodo-pentan-3-ol 
• 54783-72-1 ethyl (S)-2-(benzyloxy)propionate 
• 81445-44-5 (S)-2-(benzyloxy)propanal 

Relevant articles and documents

Chemoenzymatic approaches to SCH 56592, a new azole antifungal

Chemoenzymatic approaches to the synthesis of two key chiral precursors of a new azole antifungal agent, SCH 56592, are described. In particular, the enzymatic diastereoselective acylation of 2-benzyloxy-3-pentanol (7) was developed to produce (2S,3R)-7 in >97% diastereomeric excess (de) from otherwise unusable mixtures of (25,3R)/(2S,3S)-7 (40-80% de). The selectivity and reactivity of commercially available Candida rugosa and Mucor miehei Upases are compared for the acylation of 7 and the hydrolysis of the corresponding butyrate 16a. Of the 17 C. rugosa enzyme preparations that were examined for acylation of 7, two purified enzyme preparations showed no reactivity, five enzymes showed high diastereoselectivity with preference for the (2S,3R)-isomer, and seven showed a slight preference for the (2S,3S) isomer.

A new type of complex reagent, R4Pb / TiCl4

Tetraalkllleads (R4Pb) reacted quite smoothly with aldehydes R'CHO in the presence of TiCl4 to produce the corresponding alcohols (RCHOHR′) in high to good yields. The reagent system, R4Pb/ TiCl4, exhibited high chemoselectivity; only aldehydes underwent the alkylation in the presence of ketones. Further, the new reagent exhibited high 1,2- and 1,3-asymmetric induction. The transfer order of alkyl groups in the reaction of aldehydes with mixed tetraalkylleads/TiCl4 was determined; Me>Et.i-Pr?n-Bu.

A New Type of Stable, Storable, and Selective Alkylating Reagent, R4Pb

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