799277-48-8

Basic information

• Product Name: 5-O-[(2,4,6-trimethylphenyl)sulfonyl]-D-xylono-1,4-lactone
• Synonyms: 5-O-[(2,4,6-trimethylphenyl)sulfonyl]-D-xylono-1,4-lactone
• CAS NO: 799277-48-8
• Molecular Weight: 330.359
• Mol File: 799277-48-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 5-O-[(2,4,6-trimethylphenyl)sulfonyl]-D-xylono-1,4-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-O-[(2,4,6-trimethylphenyl)sulfonyl]-D-xylono-1,4-lactone(799277-48-8)
• EPA Substance Registry System: 5-O-[(2,4,6-trimethylphenyl)sulfonyl]-D-xylono-1,4-lactone(799277-48-8)

Safety Data

• Hazardous Substances Data: 799277-48-8(Hazardous Substances Data)

Upstream product

• 773-64-8 2-mesitylenesulphonyl chloride 
• 15384-37-9 D-xylono-1,4-lactone 

Downstream Products

• 799277-50-2 2,3-bis-O-(methoxymethyl)-5-O-[(2,4,6-trimethylphenyl)sulfonyl]-D-xylono-1,4-lactone 

Relevant articles and documents

Synthesis and oxidation of N-aminoglyconolactams: A synthesis of mannostatin A

The N-amino-ribono-1,5-lactam 4 was prepared in two high-yielding steps from the known methanesulfonate 2. Oxidation of 4 with t-BuOCl in the presence of 2,6-lutidine afforded the tetrazene 6 (63%). Oxidation with MnO2 gave the deaminated lactam 7 (40%), which was also obtained, together with the lactone 8, upon oxidation of 4 with PhSeO2H. Oxidation with Mn(OAc)3/Cu(OAc)2 provided the lactam 7 as the major and the dimer 9 as the minor product. Oxidation of 4 with 3 equiv. of Pb(OAc)4 in toluene at room temperature gave two cyclopentanes, viz. the acetoxy epoxide 10 and the diazo ketone 11 in a combined yield of 78%. Oxidation with Pb(OBz) 4 provided 11 and the crystalline benzoyloxy epoxide 12. The crystal structure of 12 was established by X-ray analysis. The N-amino-glyconolactams 41, 46, and 51 were prepared similarly to 4. Their oxidation with Pb(OAc)4 provided the diazo ketones 56, 57, and 58 as the only isolable products. Oxidation of the N-amino-mannono-1,5-lactam 55 with Pb(OAc)4 in the presence of DMSO gave the sulfoximine 59. Mannostatin A, a strong α-mannosidase inhibitor, was synthesized from the acetoxy epoxide 10 (obtained in 48% from 4) in seven steps and in an overall yield of 45%.