69892-34-8

Basic information

• Product Name: methyl 2-acetamido-2-deoxy-6-O-triphenylmethyl-β-D-glucopyranoside
• Synonyms: methyl 2-acetamido-2-deoxy-6-O-triphenylmethyl-β-D-glucopyranoside
• CAS NO: 69892-34-8
• Molecular Weight: 477.557
• Mol File: 69892-34-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: methyl 2-acetamido-2-deoxy-6-O-triphenylmethyl-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-acetamido-2-deoxy-6-O-triphenylmethyl-β-D-glucopyranoside(69892-34-8)
• EPA Substance Registry System: methyl 2-acetamido-2-deoxy-6-O-triphenylmethyl-β-D-glucopyranoside(69892-34-8)

Safety Data

• Hazardous Substances Data: 69892-34-8(Hazardous Substances Data)

Upstream product

• 7512-17-6 N-Acetyl-D-glucosamine 
• 76-83-5 trityl chloride 
• 3055-46-7 N-((4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-acetamide 
• 3055-46-7 methyl N-acetyl-D-glucosamine 
• 3946-01-8 methyl N-acetyl-β-D-glucosaminide 
• 72-87-7 N-acetyl-D-glucosamine 

Downstream Products

• 412926-35-3 methyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-6-O-triphenylmethyl-β-D-glucopyranoside 
• 69892-50-8 N-((3R,4R,5S,6R)-4,5-Bis-benzyloxy-2-methoxy-6-trityloxymethyl-tetrahydro-pyran-3-yl)-acetamide 
• 69940-08-5 N-((1S,2R,3R,4S,5R,6S)-2,3-Bis-benzyloxy-4,6-dihydroxy-5-nitro-cyclohexyl)-acetamide 
• 69940-09-6 Acetic acid (1S,2R,3S,4S,5R,6S)-3-acetoxy-4-acetylamino-5,6-bis-benzyloxy-2-nitro-cyclohexyl ester 
• 6216-31-5 2-deoxystreptamine pentaacetate 
• 14187-81-6 (1α,2β,3α,4β,6β)-4,6-Diamino-1,2,3-cyclohexantriol 
• 69892-52-0 2-acetamido-3,4-di-O-benzyl-2-deoxy-D-glucopyranoside 
• 81308-74-9 N-((1S,2R,3R)-2,3-Bis-benzyloxy-5-nitro-cyclohexyl)-acetamide 
• 81308-76-1 N-((1S,2R,3R,4S,5R)-2,3-Bis-benzyloxy-4-hydroxy-5-nitro-cyclohexyl)-acetamide 
• 81308-75-0 Acetic acid (1S,2S,3R,4R,5S,6S)-2-acetylamino-3,4-bis-benzyloxy-5-hydroxy-6-nitro-cyclohexyl ester 

Relevant articles and documents

Synthesis and biological evaluation of a radiolabeled analog of methyl 2-acetamido-2,4-dideoxy-β-D-xylo-hexopyranoside directed towards influencing cellular glycosaminoglycan biosynthesis

Two methods are presented for the synthesis of methyl 2-acetamido-2,4-dideoxy-β-D-xylo-hexopyranoside. The first method employs the Barton-McCombie deoxygenation methodology, and the second method utilizes an oxidation-β-elimination methodology that allows for the incorporation of hydrogen isotopes into the title compound. Hence, methyl 2-acetamido-2,4-dideoxy-β-D-xylo-hexopyranoside (4) and methyl 2-acetamido-2,4-dideoxy-β-D-xylo-hexopyranoside-6-t (14) were synthesized and evaluated for their ability to inhibit hepatocyte, cell-surface glycosaminoglycan biosynthesis and to incorporate a [3H] radiolabel into isolated glycosaminoglycans, respectively. Compound 4, at a concentration of 1.0 mM, demonstrated a reduction of D-[3H]glucosamine and [35S]sulfate incorporation into isolated glycosaminoglycans by 69 and 59%, of the control cultures, respectively. At 10 and 20 mM, 4 demonstrated a maximum inhibition of incorporation of both radiolabels to approximately 10% of the control cultures. Compound 14 demonstrated a maximum incorporation of a [3H] radiolabel into isolated cell-surface glycosaminoglycans at 10 and 20 mM. The mechanism of inhibition of glycosaminoglycan biosynthesis is due, in part, to the incorporation of a 4-deoxy moiety into glycosaminoglycan chains resulting in premature chain termination.

REDUCTIVE ONE-STEP ELIMINATION OF AN ACETOXYL RESIDUE AT β-POSITION OF A NITRO GROUP: SYNTHESES OF (-)-SHIKIMIC ACID FROM D-MANNOSE AND 2-DEOXYSTREPTAMINE PENTAACETATE FROM N-ACETYL-D-GLUCOSAMINE

By utilizing a reductive one-step elimination reaction of an acetoxyl residue at β-position of the nitro group in cyclitols, a synthesis of the ketocyclitol triacetate (15a), which was already converted to (-)-shikimic acid (16) and (-)-guinic acid (17), from D-mannose (4) and a conversion from N-acetyl-D-glucosamine (18) to 2-deoxystreptamine pentaacetate (22) have been accomplished.