2595-39-3

Basic information

• Product Name: 1-O-Methyl-N,3-O,4-O,6-O-tetraacetyl-α-D-glucosamine
• Synonyms: 1-O-Methyl-N,3-O,4-O,6-O-tetraacetyl-α-D-glucosamine;Methyl 2-(acetylamino)-2-deoxy-α-D-glucopyranoside 3,4,6-triacetate;Methyl 3-O,4-O,6-O-triacetyl-2-(acetylamino)-2-deoxy-α-D-glucopyranoside
• CAS NO: 2595-39-3
• Molecular Formula: C₁₅H₂₃NO₉
• Molecular Weight: 361.34442
• Mol File: 2595-39-3.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-O-Methyl-N,3-O,4-O,6-O-tetraacetyl-α-D-glucosamine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O-Methyl-N,3-O,4-O,6-O-tetraacetyl-α-D-glucosamine(2595-39-3)
• EPA Substance Registry System: 1-O-Methyl-N,3-O,4-O,6-O-tetraacetyl-α-D-glucosamine(2595-39-3)

Safety Data

• Hazardous Substances Data: 2595-39-3(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 14131-64-7 N-acetyl-D-mannosamine 
• 108-24-7 acetic anhydride 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 426833-52-5 dictyoglucosamine A 
• 10294-12-9 2-deoxy-2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranose 
• 84048-43-1 2-acetamido-2-deoxy-α,β-D-glucopyranoside 
• 1054653-39-2 Octadecanoic acid (2S,3R,4R,5S,6R)-3-acetylamino-2-allyloxy-5-hydroxy-6-propionyloxymethyl-tetrahydro-pyran-4-yl ester 
• 1053704-58-7 Octadecanoic acid (2S,3R,4R,5S,6R)-3-acetylamino-2-allyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester 
• 95069-09-3 allyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside 
• 297132-68-4 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl diphenylphosphinate 
• 2771-48-4 methyl 2-acetamido-3,4,6-O-triacetyl-2-deoxy-β-D-glucopyranoside 
• 439-02-1 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl fluoride 
• 84868-33-7 methyl 2-acetamido-3,4-di-O-acetyl-2-desoxy-α-D-glucopyranoside 

Downstream Products

• 6082-04-8 methyl 2-acetylamido-2-deoxy-D-glucoside 
• 76567-85-6 methyl 2-acetamido-6-O-acetyl-2-deoxy-α-D-glucopyranoside 
• 113159-04-9 methyl-[2-acetylamino-O⁴,O⁶-((Ξ)-benzylidene)-2-deoxy-α-D-gulopyranoside] 
• 139760-30-8 Methyl O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-O-(3,4,6-tri-O-acetyl-α-D-galactopyranosyl)-(1->3)-2-acetamido-2-deoxy-4,6-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-glucopyranoside 
• 139760-35-3 Methyl O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-O-(3,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->3)-2-acetamido-2-deoxy-4,6-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-D-glucopyranoside 
• 53756-24-4 ((2R,3S,4R,5R,6S)-5-acetamido-3,4-dihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)methyl 4-methylbenzenesulfonate 
• 3006-60-8 Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-4-yl ester 

Relevant articles and documents

Direct glycosylation of unprotected and unactivated sugars using bismuth nitrate pentahydrate

Bi(NO3)3, a low-cost, mild, and environmentally green catalyst, has been successfully utilized for Fischer glycosylation for the synthesis of alkyl/aryl glycopyranosides by reacting unprotected sugars, namely, D-glucose, L-rhamnose, D-galactose, D-arabinose, and N-acetyl-D-glucosamine with various alcohols in good to excellent yields. The glycosides were formed with high α-selectivity. Further, an expedient separation of α- and β-glycosides using silver nitrate-impregnated silica gel flash liquid chromatography has been developed.

Furanodictine A and B: Amino sugar analogues produced by cellular slime mold Dictyostelium discoideum showing neuronal differentiation activity

We investigated the constituents of Dictyostelium discoideum to clarify the diversity of secondary metabolites of Dictyostelium cellular slime molds and to explore biologically active substances that could be useful in the development of novel drugs. From a methanol extract of the multicellular fruit body of D. discoideum, we isolated two novel amino sugar analogues, furanodictine A (1) and B (2). They are the first 3,6-anhydrosugars to be isolated from natural sources. Their relative structures were elucidated by spectral means, and the absolute configurations were confirmed by asymmetric syntheses of 1 and 2. These furanodictines potently induce neuronal differentiation of rat pheochromocytoma (PC-12) cells.

Preparations and reactions of acylated and partially acylated glycosyl fluorides

Partial acylation of glycosyl fluorides in the galacto (2 and 3) and gluco series (8-10) is readily achieved. Attempts to further alkylate these acyl derivatives failed. Treatment of 2 with Lewis acid, however, provided a facile route to the 1,4-anhydro derivative 5. Lewis acid-mediated glycosylation of 2-acetamido-3,4,6-tri-O-acetyl-α-D-glucopyranosyl fluoride 11 led to the simple glycosides and thioglycosides 12-16. Similarly, in the galacto series (17) an advantageous route to the β-galactosidase inhibitor 19 could be elaborated.