158976-98-8

Basic information

• Product Name: L-threo-Pentonic acid, 2-deoxy-3,5-bis-O-(phenylmethyl)-, .gamma.-lactone
• Synonyms: L-threo-Pentonic acid, 2-deoxy-3,5-bis-O-(phenylmethyl)-, .gamma.-lactone
• CAS NO: 158976-98-8
• Molecular Formula: C₁₉H₂₀O₄
• Molecular Weight: 312.36
• Mol File: 158976-98-8.mol

Chemical Properties

• Boiling Point: 474.0±40.0 °C(Predicted)
• Appearance: /
• Density: 1.18±0.1 g/cm3(Predicted)
• CAS DataBase Reference: L-threo-Pentonic acid, 2-deoxy-3,5-bis-O-(phenylmethyl)-, .gamma.-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: L-threo-Pentonic acid, 2-deoxy-3,5-bis-O-(phenylmethyl)-, .gamma.-lactone(158976-98-8)
• EPA Substance Registry System: L-threo-Pentonic acid, 2-deoxy-3,5-bis-O-(phenylmethyl)-, .gamma.-lactone(158976-98-8)

Safety Data

• Hazardous Substances Data: 158976-98-8(Hazardous Substances Data)

Upstream product

• 158976-92-2 1,3-dibenzyloxy-2-propyl-diazoacetate 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 78185-09-8 2-deoxy-D-ribonolactone-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one 
• 91510-99-5 (2S,3R)-(3-hydroxy-5-oxotetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate 
• 82130-86-7 2,5-di-O-tosyl-D-ribono-1,4-lactone 
• 5336-08-3 D-Ribono-1,4-lactone 
• 294188-24-2 3,5-di-O-acetyl-2-deoxy-L-threo-pentono-1,4-lactone 

Downstream Products

• 1054683-61-2 methanesulfonic acid (1S,2S)-2-benzyloxy-1-benzyloxymethyl-4-methanesulfonyloxybutyl ester 
• 294188-27-5 N-benzyl-3,5-di-O-benzyl-1,2,4-trideoxy-1,4-imino-D-erythro-pentitol 
• 294188-28-6 3,5-di-O-benzyl-1,2,4-trideoxy-1,4-imino-D-erythro-pentitol 
• 98900-30-2 (2R,3S)-2-hydroxymethyl-3-hydroxypyrrolidinium hydrochloride 
• 294188-25-3 (3S,4S)-3,5-bis(benzyloxy)pentane-1,4-diol 

Relevant articles and documents

A new stereospecific synthesis of 1,2,4-Trideoxy-1,4-imino-D-erythro-pentitol

1,2,4-Trideoxy-1,4-imino-D-erythro-pentitol [(2R,3S)-3-hydroxy-2-hydroxymethylpyrrolidine] (4) was synthesised from 2,5-di-O-tosyl-D-ribono-1,4-lactone in 42 % overall yield. The key steps were deoxygenation at C-2 and a stereospecific inversion of the co

Enantioselective Syntheses of 2-Deoxyxylono-1,4-lactone and 2-Deoxyribono-1,4-lactone from 1,3-Dioxan-5-yl Diazoacetates

1,3-Dioxan-5-yl diazoacetates are valuable substrates for highly diastereoselective and enantio-selective carbon-hydrogen insertion reactions. trans-2-(tert-Butyl)-1,3-dioxan-5-yl diazoacetate is a direct precursor to 2-deoxyribono-1,4-lactone in up to 81% ee, whereas cis-2-(tert-butyl)-1,3-dioxan-5-yl diazoacetate yields only the protected 2-deoxyxylono-1,4-lactone in up to 96% ee. However, trans-2-aryl-1,3-dioxan-5-yl diazoacetate (aryl = phenyl or 2-naphthyl) forms the precursor to 2-deoxyxylono-1,4-lactone in up to 95% ee but with the mirror image configuration of that produced from the trans-2-(tert-butyl) analogue. The catalysts that are most suitable for these carbon-hydrogen insertion reactions are chiral dirhodium(II) carboxamidates. 1,3-Dialkoxy-2-propyl diazoacetates give mainly 2-deoxyxylono-1,4-lactone derivatives (>90:10) with generally high enantiocontrol, but replacement of hydrogen at the 2-position of these 2-propyl diazoacetates led to a mixture of products.

SYNTHESIS OF 2-DEOXYXYLOLACTONE FROM GLYCEROL DERIVATIVES VIA HIGHLY ENANTIOSELECTIVE CARBON-HYDROGEN INSERTION REACTIONS

diazodecomposition of 1,3-dialkoxy-2-propyl diazoacetates catalyzed by chiral dirhodium(II) carboxamides results in highly enantioselective and diastereoseelctive carbon-hydrogen insertion which forms 3,5-dialkyl 2-deoxyxylolactones in up to 98percent enantiomeric excess.