128678-42-2

Basic information

• Product Name: xylo-Hexodialdose, 2,5-anhydro-3,4-dideoxy-3-(hydroxymethyl)- (9CI)
• Synonyms: xylo-Hexodialdose, 2,5-anhydro-3,4-dideoxy-3-(hydroxymethyl)- (9CI)
• CAS NO: 128678-42-2
• Molecular Formula: C7H10O4
• Molecular Weight: 158.1519
• Product Categories: ALDEHYDE
• Mol File: 128678-42-2.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: xylo-Hexodialdose, 2,5-anhydro-3,4-dideoxy-3-(hydroxymethyl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: xylo-Hexodialdose, 2,5-anhydro-3,4-dideoxy-3-(hydroxymethyl)- (9CI)(128678-42-2)
• EPA Substance Registry System: xylo-Hexodialdose, 2,5-anhydro-3,4-dideoxy-3-(hydroxymethyl)- (9CI)(128678-42-2)

Safety Data

• Hazardous Substances Data: 128678-42-2(Hazardous Substances Data)

Upstream product

• 64589-24-8 (+/-)-2exo,3exo-dihydroxy-5endo-hydroxymethyl-7-oxabicyclo<2.2.1>heptane 
• 64589-25-9 (+/-)-2exo,3exo-diacetoxy-5endo-acxetoxymethyl-7-oxabicyclo<2.2.1>heptane 

Relevant articles and documents

SYNTHESIS OF (+/-)-3-AMINO-2,4-DIHYDROXY-6-HYDROXYMETHYL-8-OXABICYCLOOCTANE DERIVATIVES, AND THEIR ANHYDRO-RING-MIGRATION WITH HYDROGEN BROMIDE-ACETIC ACID

Nitromethane-mediated cyclization of the dialdehyde generated by periodate oxidation of (+/-)-2exo,3exo-dihydroxy-5endo-hydroxymethyl-7-oxabicycloheptane (2) in methanolic sodium methoxide afforded, after neutralisation, three diastereoisomers (4a-6a) of (+/-)-2,4-dihydroxy-6-hydroxymethyl-3-nitro-8-oxabicyclooctane in 52percent combined yield.Their structures were assigned on the basis of 1H-n.m.r. spectra of the respective triacetates (4b-6b).Hydrogenation of the nitro compounds in methanol-acetic anhydride with Raney nickel followed by acetylation gave the corresponding N-acetyl derivatives (4c-6c), treatment of which with 15percent hydrogen bromide-acetic acid at 80 deg replaced the primary acetoxyl group with bromine, giving the monobromo derivatives 4d-6d.Migration of the anhydro rings also occurred with 4c and 6c, yielding the respective isomers (1RS,2RS,4SR,5RS,6RS,7SR)-7-acetamido-2,6-diacetoxy-4-bromomethyl-8-oxabicyclooctane (7) and (1RS,2RS,4SR,5RS,6SR,7SR)-6-acetamido-4,7-diacetoxy-2-bromomethyl-8-oxabicyclooctane (8a).The mechanism of these reactions is considered.