58871-04-8

Basic information

• Product Name: 6-O-p-toluenesulfonyl-D-arabino-hex-1-enitol
• Synonyms: 6-O-p-toluenesulfonyl-D-arabino-hex-1-enitol
• CAS NO: 58871-04-8
• Molecular Weight: 300.332
• Mol File: 58871-04-8.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: 6-O-p-toluenesulfonyl-D-arabino-hex-1-enitol(CAS DataBase Reference)
• NIST Chemistry Reference: 6-O-p-toluenesulfonyl-D-arabino-hex-1-enitol(58871-04-8)
• EPA Substance Registry System: 6-O-p-toluenesulfonyl-D-arabino-hex-1-enitol(58871-04-8)

Safety Data

• Hazardous Substances Data: 58871-04-8(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 2873-29-2 D-glucal triacetate 
• 104-15-4 toluene-4-sulfonic acid 
• 13265-84-4 D-glucal 

Downstream Products

• 18546-25-3 6-O-p-tolylsulfonyl-3,4-di-O-acetyl-D-glucal 
• 129693-96-5 3-O-tert-Butyldimethylsilyl-6-O-tosyl-D-glucal 
• 356041-84-4 α-D-callipetose 
• 355131-38-3 1,5-anhydro-2,6-dideoxy-4-O-nosyl-D-erythro-hex-1-enit-ulose 
• 1610617-94-1 thiophenyl 3,6-anhydro-2-deoxy-β-D-glucopyranoside 
• 1610617-95-2 thiophenyl 3,6-anhydro-2-deoxy-α-D-glucopyranoside 
• 111425-52-6 thiophenyl 2,3-dideoxy-α-D-glucopyranoside 
• 1610617-96-3 thiophenyl 2,3-dideoxy-β-D-glucopyranoside 

Relevant articles and documents

Lewis acid/base pair as a catalytic system for α-stereoselective synthesis of 2-deoxyglycosides through the addition of alcohols to glycals

This report describes the α-stereoselective addition of alcohols to glycals promoted by a cooperative Lewis acid/base pair catalytic system composed of B(C6F5)3 and tetrabutylammonium bromide (TBAB), which provides access to 2-deoxylglycosides in high yields. A mechanistic investigation supported by NMR analysis highlights the possible involvement of nucleophilic addition through boron-induced activation of alcohols under the assistance of TBAB. The protocol discussed here features the high stereoselectivity, mild reaction conditions, inexpensive and stable catalysts, and a broad substrate scopes.

Asymmetric Total Synthesis of the Complex Polycyclic Xanthone FD-594

A highly convergent approach was developed to achieve the first asymmetric and scalable total synthesis of FD-594, a complex polycyclic xanthone natural product from Streptomyces sp. TA-0256, in a longest linear sequence (LLS) of 20 steps. The trans-9,10-

Total Synthesis and Biological Evaluation of the Glycosylated Macrocyclic Antibiotic Mangrolide A

The macrocyclic antibiotic mangrolide A has been described to exhibit potent activity against a number of clinically important Gram-negative pathogens. Reported is the first enantioselective total synthesis of mangrolide A and derivatives. Salient features of this synthesis include a highly convergent macrocycle preparation, stereoselective synthesis of the disaccharide moiety, and two β-selective glycosylations. The synthesis of mangrolide A and its analogues enabled the re-examination of its activity against bacterial pathogens, and only minimal activity was observed.