391928-90-8

Basic information

• Product Name: 2H-Pyran-3(6H)-one, 2-(phenylmethoxy)-, (2S)-
• CAS NO: 391928-90-8
• Molecular Formula: C12H12O3
• Molecular Weight: 204.225
• Mol File: 391928-90-8.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2H-Pyran-3(6H)-one, 2-(phenylmethoxy)-, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Pyran-3(6H)-one, 2-(phenylmethoxy)-, (2S)-(391928-90-8)
• EPA Substance Registry System: 2H-Pyran-3(6H)-one, 2-(phenylmethoxy)-, (2S)-(391928-90-8)

Safety Data

• Hazardous Substances Data: 391928-90-8(Hazardous Substances Data)

Upstream product

• 14125-76-9 1,5-anhydro-2,3,4-tri-O-acetyl-D-threo-pent-1-enitol 
• 100-51-6 benzyl alcohol 
• 30694-66-7 2,3,4-tri-O-acetyl-1,5-anhydro-D-erythro-pent-1-enitol 
• 391928-94-2 benzyl 3,4-dideoxy-α-L-glycero-pent-3-enopyranoside 
• 856175-47-8 benzyl 2-O-acetyl-3,4-dideoxy-α-L-glycero-pent-3-enopyranoside 
• 856099-29-1 benzyl 2-O-acetyl-β-D-arabinopyranoside 3,4-thionocarbonate 
• 172334-45-1 benzyl β-D-arabinopyranoside 3,4-thionocarbonate 
• 5329-50-0 (-)-benzyl β-D-arabinopyranoside 
• 108646-05-5 (3S,4R,5R)-tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate 
• 113889-50-2 (3S,4R,5R)-2-bromotetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 28697-53-2 D-arabinopyranose 
• 50837-92-8 2,3,4-tri-O-acetyl-D-xylopyranosyl bromide 

Downstream Products

• 391928-94-2 benzyl 3,4-dideoxy-α-L-glycero-pent-3-enopyranoside 
• 1610827-78-5 C₂₃H₂₅NO₅ 
• 1610827-79-6 C₂₃H₂₅NO₅ 
• 1191092-94-0 2-propyl 3-deoxy-4-S-(β-D-galactopyranosyl)-4-thio-α-D-xylo-hexopyranoside 
• 1191092-93-9 benzyl 3-deoxy-4-S-(β-D-galactopyranosyl)-4-thio-β-erythro-pentopyranoside 
• 1191092-89-3 benzyl 3-deoxy-4-S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-4-thio-β-D-threo-pentopyranoside 
• 1191092-88-2 benzyl 3-deoxy-4-S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-4-thio-β-D-erythro-pentopyranoside 
• 1191092-87-1 benzyl 3-deoxy-4-S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-4-thio-β-D-glycero-pentopyranosid-2-ulose 
• 5329-50-0 (-)-benzyl β-D-arabinopyranoside 

Relevant articles and documents

Design and Synthesis of 2-Acetamido-2,3-dideoxythiodisaccharides via Diastereoselective Conjugate Addition to Sugar Enone O-Acetyl Oximes. Galactosidase Inhibition Studies

The key step in a new synthesis of 2-acetamido-2,3-dideoxy-(14)-thiodisaccharides was the conjugate addition of a 1-thiogalactose derivative to E and Z acetyl oximes derived from sugar enones. This reaction was shown to be completely diastereoselective fo

Synthesis of enantiomerically pure enones (2-benzyloxypyran-3-ones)derived from pentoses

The useful synthons sugar enones (2-benzyloxypyran-3-ones)derived from pentoses have been prepared starting from 2-acetoxyglycals or benzyl pentopyranosides. The glycals were glycosylated with benzyl alcohol in the presence of a Lewis acid (SnCl4/su

Stereocontrolled Diels - Alder cycloadditions of sugar-derived dihydropyranones with dienes

2-Acetoxy-3,4-di-O-acetyl-D-arabinal (6), similar to its D-xylo analogue 4, reacted with benzyl alcohol by the tin(IV) chloride-promoted glycosylation to produce optically active (S)-2-benzyloxy-2H-pyran-3(6H)-one (8a). The L-arabinal derivative (5) gave 9a, the dihydropyranone enantiomer of 8a. These results indicated that the configuration of the C-4 stereocenter in the starting glycal defines the configuration of the new chiral center in the resulting dihydropyranone. The influence of other catalysts (BF3 or iodine) employed for the glycosylation on the optical purity of the dihydropyranone was studied. Enantiomerically pure dihydropyranones 8b and 9c were obtained using chiral alcohols ((R)- and (S)-2-octanol, respectively) as glycosylating agents. Compounds 8a,b and 9a,c proved to be reactive dienophiles in thermal and Lewis acid-promoted Diels - Alder reactions. The addition of 2,3-dimethylbutadiene, cyclopentadiene, and 1,3-cyclohexadiene to the β-pyranones 8a,b led to the corresponding adducts 10a,b, 12a,b, and 16a,b as major products. Enantiomeric cycloadducts were synthesized from the α-pyranones 9a,c. The main products were formed by highly facial-diastereoselective addition of dienes to the pyranone ring, guided by the sterical hindrance of the alkoxy substituent of the C-2 stereocenter. As cycloadditions with cycloalkadienes were also highly endo diastereoselective, these reactions gave access to pure tetrahydrobenzopyranones that carry a multitude of stereogenic centers installed in a predictable way.