89539-31-1

Upstream product

• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 6748-85-2 methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 98-88-4 benzoyl chloride 
• 1125-88-8 benzaldehyde dimethyl acetal 

Downstream Products

• 1415663-31-8 5-(4-O-benzyl-mycaminosyl)-3-O-descladinosyl-6-O-methyl-3-oxo-erythronolide A?11,12-cyclic carbonate 
• 1415663-30-7 5-(2-O-benzoyl-4-O-benzyl-mycaminosyl)-3-O-descladinosyl-6-O-methyl-3-oxo-erythronolide A 11,12-cyclic carbonate 
• 1415663-28-3 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranosyl trichloroacetimidate 
• 1415663-27-2 C₁₇H₂₅NO₄S 
• 1415663-26-1 ethyl 2-O-benzoyl-3,6-dideoxy-3-dimethylamino-1-thio-β-D-glucopyranoside 
• 1415663-25-0 C₂₂H₂₇NO₄S 
• 1415663-24-9 p-methylphenyl 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-1-thio-β-D-glucopyranoside 
• 1415663-36-3 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-β-D-glucopyranosyl fluoride 
• 1415663-29-4 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranosyl fluoride 
• 1415663-22-7 1-O-acetyl-2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-D-glucopyranose 
• 1415663-21-6 methyl 2-O-benzoyl-4-O-benzyl-3,6-dideoxy-3-dimethylamino-α-D-glucopyranoside 
• 109923-12-8 methyl 2,3-anhydro-4-O-benzyl-6-deoxy-α-D-allopyranoside 
• 109923-11-7 methyl 4-O-benzyl-6-deoxy-2,3-di-O-p-tolylsulfonyl-α-D-glucopyranoside 
• 114827-98-4 Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-4-benzyloxy-2-((2R,3R,4R,5R,6S)-3-benzyloxy-5-hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-4-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester 

Relevant academic research and scientific papers

Cyanuric chloride/sodium borohydride: A new reagent combination for reductive opening of 4,6-benzylidene acetals of carbohydrates to primary alcohols

In the first such example, NaBH4 in combination with cyanuric chloride (TCT) has been used to obtain 6-hydroxy-4-benzyl ether derivatives from 4,6-benzylidene acetals of carbohydrates. The nature of hydride donor determines the regioselectivity

Synthesis and antibacterial activity of novel modified 5-O-desosamine ketolides

A series of novel modified 5-O-desosamine-ketolides were synthesized. The 5-O-desosamine fragment was removed from ketolide by an efficient and mild manipulation. 4-O-substituted desosamine was introduced into the ketolide aglycon and various coupling methods were essayed for the glycosylation. Three novel ketolides were tested for in vitro antibacterial activity against a panel of susceptible and resistant pathogens. Compound 26 showed potent activity against all the methicillin-sensitivity and resistant pathogens.

Some observations on the reductive ring opening of 4,6-O-benzylidene acetals of hexopyranosides with the borane trimethylamine-aluminium chloride reagent

Reductive ring openings of 3-O-benzoyl-4,6-O-benzylidene-d-glucopyranosides with BH3·NMe3-AlCl3 are accompanied by side reactions, such as debenzoylation and reduction of the benzoate to benzyl ether. This phenomenon was r

Metal trifluoromethanesulfonate-catalyzed regioselective reductive ring opening of benzylidene acetals

A systematic study of various metal trifluoromethanesulfonates as efficient catalysts in the regioselective reductive ring opening of benzylidene acetals is described, including the effects of solvents, reducing agents, and temperature. These catalysts are found to be effective in cleaving the 4,6-O-acetal rings of hexopyranosides at either O4 or O6, respectively. When used in conjunction with a 1 M solution of BH3.THF in THF without extra addition of any solvent, it affects the ring fission at the O6 position to generate the corresponding primary alcohols, whereas O4-opening takes place in acetonitrile in the presence of dimethylethylsilane as the reductant leading to the secondary hydroxyl derivatives in high selectivity and yields. These methodologies can be applied to a wide range of substrates containing various functional groups.

Regio- and chemoselective reductive cleavage of 4,6-O-benzylidene-type acetals of hexopyranosides using BH3·THF-TMSOTf

Benzylidene-type cyclic acetals of carbohydrates undergo efficient reductive ring opening using BH3·THF and a catalytic amount of TMSOTf at room temperature. 4,6-O-Benzylidene-hexopyranosides afford the corresponding 4-O-benzyl ethers exclusive

Cu(OTf)2 as an efficient and dual-purpose catalyst in the regioselective reductive ring opening of benzylidene acetals

(Chemical Equation Presented) Reducing the choices. Cu(OTf)2 is an efficient and dual-purpose catalyst for the highly regioselective reductive ring openings of benzylidene acetals with either BH3 or Me 2EtSiH to give the corresponding primary and secondary alcohols (see scheme). Isotope studies have confirmed that both modes of ring cleavage proceed by an SN1 reaction pathway when borane or silane attack the acetal carbon center.

Metal trifluoromethanesulfonate-catalyzed regioselective borane-reductive ring opening of benzylidene acetals: A concise synthesis of 1,4-dideoxy-1,4-imino-L-xylitol

(equation presented) A highly regioselective borane-reductive ring opening of the 4,6-O-benzylidene-D-hexopyranosides to the corresponding 6-alcohols in excellent yields at room temperature via various metal trifluoromethanesulfonates as catalysts is desc

Phyllanthoside-Phyllanthostatin Synthetic Studies. 9. Total Syntheses of (-)-Phyllanthostatin 1, (+)-Phyllanthostatin 2, and (+)-Phyllanthostatin 3

Phyllanthostatins 1, 2, and 3 (2-4) have been synthesized for the first time. The unusual 1′→2β glycosidic linkages of the disaccharide moieties were constructed via anchimerically-assisted Koenigs-Knorr reactions. The novel β-glycosyl esters were then ge