14187-68-9

Basic information

• Product Name: methyl 4,6-O-benzylidene-2-O-[(4-methylphenyl)sulfonyl]hexopyranoside
• Synonyms: Methyl 4,6-O-benzylidene-2-O-[(4-methylphenyl)sulfonyl]hexopyranoside
• CAS NO: 14187-68-9
• Molecular Formula: C₂₁H₂₄O₈S
• Molecular Weight: 436.4755
• Mol File: 14187-68-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 629.8°C at 760 mmHg
• Flash Point: 334.7°C
• Density: 1.4g/cm³
• Vapor Pressure: 9.99E-17mmHg at 25°C
• Refractive Index: 1.613
• CAS DataBase Reference: methyl 4,6-O-benzylidene-2-O-[(4-methylphenyl)sulfonyl]hexopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4,6-O-benzylidene-2-O-[(4-methylphenyl)sulfonyl]hexopyranoside(14187-68-9)
• EPA Substance Registry System: methyl 4,6-O-benzylidene-2-O-[(4-methylphenyl)sulfonyl]hexopyranoside(14187-68-9)

Safety Data

• Hazardous Substances Data: 14187-68-9(Hazardous Substances Data)

Upstream product

• 14155-23-8 methyl 4,6-O-benzylidene-β-D-glucopyranoside 
• 98-59-9 p-toluenesulfonyl chloride 
• 14200-01-2 methyl 4,6-O-benzylidene-2-O-p-tolylsulfonyl-3-O-acetyl-β-D-glucopyranoside 

Downstream Products

• 14187-72-5 methyl 4,6-O-benzylidene-3-deoxy-β-D-arabino-hexopyranoside 
• 30010-02-7 methyl 4,6-O-benzylidene-2,3-di-O-p-tolylsulfonyl-β-D-glucopyranoside 
• 65725-24-8 methyl 4,6-O-benzylidene-2-deoxy-β-D-ribo-hexopyranoside 
• 52612-68-7 methyl 4,6-O-benzylidene-2-deoxy-β-D-arabino-hexopyranoside 
• 24921-02-6 methyl 3-deoxy-4,6-O-benzylidene-β-D-allopyranoside 
• 14187-71-4 Methyl 2,3-anhydro-4,6-O-benzylidene-β-D-allopyranoside 
• 14187-69-0 methyl 4,6-O-benzylidene-3-O-p-tolylsulfonyl-β-D-glucopyranoside 
• 14200-01-2 methyl 4,6-O-benzylidene-2-O-p-tolylsulfonyl-3-O-acetyl-β-D-glucopyranoside 
• 14155-23-8 methyl 4,6-O-benzylidene-β-D-glucopyranoside 

Relevant articles and documents

Silver(I) oxide mediated selective monoprotection of diols in pyranosides

The reaction of 4,6-O-benzylidene-D-pyranosides with a stoichiometric amount of TsCl, AcCl, and BzCl in the presence of silver(I) oxide and a catalytic amount of potassium iodide led to monosubstituted derivatives in high regioselectivity and in good yiel

DESULFONYLOXYLATION OF SOME SECONDARY p-TOLUENESULFONATES OF GLYCOSIDES BY LITHIUM TRIETHYLBOROHYDRIDE; A HIGH-YIELDING ROUTE TO 2- AND 3-DEOXY SUGARS

Lithium triethylborohydride (LTBH) reacts readily with p-toluenesulfonates of methyl 4,6-O-benzylidene-α-D-glucopyranoside (4) to give deoxyglycosides in >90percent yield.Thus, the 2,3-ditosylate (1) and the 3-monotosylate (2) thereof afford methyl 4,6-O-benzylidene-2-deoxy-α-D-ribo-hexopyranoside (7) in highly regio- and stereo-selective reactions that proceed via methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside (6), and the 2-monotosylate (8) of 4 gives the 3-deoxy-α-D-arabino isomer (12) of 7 via the corresponding 2,3-anhydro-α-D-mannopyranoside 11.In the series of the corresponding β anomers, the 3-monotosylate 14 and the 2-monotosylate 16 are similarly desulfonyloxylated, with equal ease, but furnish mixtures of regioisomeric deoxyglycosides, namely, the 3- and 2-deoxy-β-D-ribo derivatives 20 and 21, and the 2- and 3-deoxy-β-D-arabino derivatives 22 and 23, respectively.It could be shown that this difference is due to the failure of the intermediary, β-glycosidic epoxides 18 and 19 (the anomers of 6 and 11) to obey the Fuerst-Plattner rule in their reductive ring-opening with LTBH.The β-glycosidic 2,3-ditosylate 15 reacts less readily, and gives 20-23, with 20 preponderating.The 2-O-methyl-3-O-tosyl-β-D-glucopyranoside 24 is partly desulfonylated and partly desulfonyloxylated, whereas its 3-O-methyl-2-O-tosyl isomer 27 undergoes desulfonylation exclusively.The reductions of 1, 2, and 8 by LTBH are compared with those previously effected by lithium aluminum hydride, which are slower, involve considerable desulfonylation, and afford lower yields of deoxyglycosides, with the main products differing from those obtained by the action of LTBH.Mechanistic differences associated with the two reductants are discussed.