69892-34-8

Upstream product

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

Downstream Products

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

Relevant academic research and scientific papers

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.

Marine natural products. XXVIII. The structures of sarasinosides A1, A2, A3, B1, B2, B3, C1, C2, and C3, nine new norlanostane-triterpenoidal oligoglycosides from the palauan marine sponge Asteropus sarasinosum

The chemical structures of sarasinosides A1, A2, A3, B1, B2, B3, C1, C2, and C3, nine 30-norlanostane-triterpenoidal oligoglycosides isolated from the Palauan marine sponge Asteropus sarasinosum have been elucidated on the basis of chemical and physicochemical evidence. Sarasinosides A2 (2) and A3 (3) were shown to he the 7,9(11)-diene and 8,14-diene analogs of sarasinoside A1 (1), whereas sarasinosides B2 (7) and B3 (9) were the 7,9(11)-diene and 8,14-diene analogs of sarasinoside B1 (5), respectively. Similar structural correlations of sarasinosides C2 (6) and C3 (8) with sarasinoside C1 (4) were demonstrated. These sarasinosides characteristically contain one mole each of N-acetylglucosamine and N-acetylgalactosamine in their oligosaccharide moieties.

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.