13639-55-9

Basic information

• Product Name: tert-butyl 2,3,4,6-tetra-O-acetyl-1-thiohexopyranoside
• CAS NO: 13639-55-9
• Molecular Formula: C₁₈H₂₈O₉S
• Molecular Weight: 420.4745
• Mol File: 13639-55-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 469.3°C at 760 mmHg
• Flash Point: 217.7°C
• Density: 1.23g/cm³
• Vapor Pressure: 5.58E-09mmHg at 25°C
• Refractive Index: 1.499
• CAS DataBase Reference: tert-butyl 2,3,4,6-tetra-O-acetyl-1-thiohexopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 2,3,4,6-tetra-O-acetyl-1-thiohexopyranoside(13639-55-9)
• EPA Substance Registry System: tert-butyl 2,3,4,6-tetra-O-acetyl-1-thiohexopyranoside(13639-55-9)

Safety Data

• Hazardous Substances Data: 13639-55-9(Hazardous Substances Data)

Upstream product

• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 75-66-1 2-methylpropan-2-thiol 
• 2280-44-6 D-Glucose 
• 604-69-3 β-D-glucose pentaacetate 
• 66791-49-9 1-(tert-butylsulfanyl)-2-(trimethylsilyl)ethane 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 108-24-7 acetic anhydride 
• 94198-62-6 tert-butyl 1-thio-D-glucopyranoside 
• 112288-70-7 (2R,3R,4S,5R)-6,6-Bis-tert-butylsulfanyl-hexane-1,2,3,4,5-pentaol 

Relevant articles and documents

Silver fluoroborate promoted sulfur alkylation of β-silyl ethyl sulfides. Selective synthesis of β-thioglycosides

Silver (I) activation of α-glucosyl bromide in the presence of 2-trimethylsilylethyl sulfides as sulfur nucleophiles selectively provides β-thioglycosides.

Dehydrative Thioglycosylation of 1-Hydroxyl Glycosides Catalyzed by In Situ-Generated AlI3

Thioglycosylation of 1-hydroxyl glycosides catalyzed by in situ-generated AlI3 from elemental aluminium and molecular iodine has been developed. This method provides an alternative route to access anomeric thioglycosides without the use of hazard Lewis acidic activators or per-modified activated thiol sources. The major advantages of this dehydrative procedure are environmental friendly, ease of operation, high anomeric diastereoselectivity, and mild reaction conditions.

Involvement of the S-aglycon in the conformational preferences of thioglucosides

The conformational preferences of two series of alkyl β-d-thioglucopyranosides in solution were investigated by NMR and CD. The rotamer populations of the hydroxymethyl group were found to depend on the structural nature of the S-aglycon. The population of the gt rotamer increased and that of the gg rotamer decreased as the alkyl group attached to the S atom increased in size. These rotamer populations have a linear correlation with the Taft' steric parameters, the nS s(-) σC s(-) O* exo-anomeric interaction may express these rotational preferences. Comparative analysis of the hydroxymethyl populations between alkyl O- and S-glucosides revealed identical or slightly higher gt and smaller gg populations for the latter compounds.

Stereoselective 1,2-CIS-1-thioglycosidation of aldohexoses with tert-butyl mercaptan in 90% trifluoroacetic acid

tert-Butyl 1,2-cis-1-thioglycopyranosides of various aldohexoses (D-glucose, D-galactose, D-mannose, and L-rhamnose), and disaccharides (cellobiose, lactose, and maltose) were preferentially prepared in good yields by reacting the corresponding free sugar