106064-44-2

Basic information

• Product Name: Pentanoic acid, 3-hydroxy-5-(phenylmethoxy)-, 2-methylpropyl ester, (S)-
• CAS NO: 106064-44-2
• Molecular Formula: C16H24O4
• Molecular Weight: 280.364
• Mol File: 106064-44-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Pentanoic acid, 3-hydroxy-5-(phenylmethoxy)-, 2-methylpropyl ester, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Pentanoic acid, 3-hydroxy-5-(phenylmethoxy)-, 2-methylpropyl ester, (S)-(106064-44-2)
• EPA Substance Registry System: Pentanoic acid, 3-hydroxy-5-(phenylmethoxy)-, 2-methylpropyl ester, (S)-(106064-44-2)

Safety Data

• Hazardous Substances Data: 106064-44-2(Hazardous Substances Data)

Upstream product

• 106064-33-9 isobutyl 5-(benzyloxy)-3-oxopentanoate 
• 501-53-1 benzyl chloroformate 
• 7779-75-1 isobutyl acetoacetate 
• 3587-60-8 Benzyloxymethyl chloride 

Downstream Products

• 88818-17-1 (R)-1-phenylmethoxyoct-7-en-3-ol 
• 106064-55-5 Methanesulfonic acid (S)-1-allyl-5-benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-pentyl ester 
• 106064-57-7 [(S)-1-(2-Benzyloxy-ethyl)-3-iodo-hex-5-enyloxy]-tert-butyl-diphenyl-silane 
• 106064-53-3 8-(benzyloxy)-6-((tert-butyldiphenylsilyl)oxy)-4-hydroxy-1-octene 
• 106064-52-2 (S)-5-(benzyloxy)-3-(tert-butyldiphenylsiloxy)pentanal 
• 106064-59-9 [(R)-1-(2-Benzyloxy-ethyl)-hex-5-enyloxy]-tert-butyl-diphenyl-silane 
• 106064-51-1 5(S)-(benzyloxy)-3-((tert-butyldiphenylsilyl)oxy)pentanol 
• 189026-26-4 C₂₉H₃₆N₂O₁₀ 
• 189026-25-3 C₂₇H₃₄N₂O₉ 
• 189026-29-7 (3S,4S)-4-Acetoxy-2-((R)-3-acetyl-2-oxo-oxazolidine-4-carbonyl)-2,3,4,5-tetrahydro-pyridazine-3-carboxylic acid isobutyl ester 
• 221627-52-7 [(3S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-5-triisopropylsilanyloxy-oct-7-enyloxymethyl]-benzene 
• 221627-50-5 [(3S,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-5-triisopropylsilanyloxy-oct-7-enyloxymethyl]-benzene 
• 221627-25-4 (3S,5S,6R)-1-Benzyloxy-6-methyl-5-triisopropylsilanyloxy-oct-7-en-3-ol 
• 221627-27-6 (3S,5R,6S)-1-Benzyloxy-6-methyl-5-triisopropylsilanyloxy-oct-7-en-3-ol 

Relevant articles and documents

Total synthesis of polycavernoside A, a lethal toxin of the red alga Polycavernosa tsudai

Two approaches to the synthesis of the aglycon 120 of polycavernoside A (1) were developed, only one of which was completed. The successful "second-generation" route assembled the aglycon seco acids 102 and 106 via Nozaki-Hiyama-Kishi coupling of aldehyde 70, prepared from methyl (S)-3-hydroxy-2-methylpropionate (72) and (S)-pantolactone (73), with vinyl bromide 71. The latter was obtained from a sequence which commenced from the silyl ether 24 of 3-hydroxypropionaldehyde and entailed cyclization of (Z)-ζ-hydroxy-α,β-unsaturated ester 82. Regioselective Yamaguchi lactonization of trihydroxycarboxylic acids 102 and 106 and subsequent functional-group adjustments led to macrolactone 120, to which the fucopyranosylxylopyranoside moiety was attached. Stille coupling of the glycosidated aglycon 128 with dienylstannane 129 furnished polycavernoside A in a synthesis for which the longest linear sequence was 25 steps. The overall yield to lactone 120 was 4.7%.

Substrate modification as a means of enhancing the enantioselectivity of microbial reductions of β-keto esters. An (R)- or (S )-1,3,5-trihydroxypentane synthon

The enantioselectivity of yeast-mediated reduction of 5-(benzyloxy)-3-oxopentanoate esters can be optimized by simple selection of a suitable ester alkoxy group. The resulting chiral 5-(benzyloxy)-3-hydroxypentanoates with > 95% ee can serve as either an (R)- or (S)-1,3,5-trihydroxypentane synthon for asymmetric syntheses. The synthesis of a key optically active intermediate for (S)-(-)-lipoic acid is provided as an example.