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

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

Diols obtained via chemo and regioselective ring opening of epoxy alcohols: A straightforward synthesis of 2S,3S-octandiol

Epoxy alcohols are regio and chemoselectively opened to the corresponding iodohydrins and then reduced in situ to diols; the application of the described procedure leads to a short asymmetric of a well known pheromone. Also homoallylic (E and Z) epoxy alcohols and its benzylated derivatives shows high preference for regioselective opening affording the corresponding 1,3 diol.

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

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