104652-05-3

Basic information

• Product Name: methyl 3-O-benzoyl-2,6-dideoxy-α-D-ribo-hexopyranoside
• Synonyms: methyl 3-O-benzoyl-2,6-dideoxy-α-D-ribo-hexopyranoside
• CAS NO: 104652-05-3
• Molecular Weight: 266.294
• Mol File: 104652-05-3.mol

Chemical Properties

• CAS DataBase Reference: methyl 3-O-benzoyl-2,6-dideoxy-α-D-ribo-hexopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3-O-benzoyl-2,6-dideoxy-α-D-ribo-hexopyranoside(104652-05-3)
• EPA Substance Registry System: methyl 3-O-benzoyl-2,6-dideoxy-α-D-ribo-hexopyranoside(104652-05-3)

Safety Data

• Hazardous Substances Data: 104652-05-3(Hazardous Substances Data)

Upstream product

• 93960-50-0 Benzoic acid (2S,3S,4S,6S)-2-bromomethyl-3-hydroxy-6-methoxy-tetrahydro-pyran-4-yl ester 
• 18944-96-2 methyl 4-O-benzoyl-2,6-dideoxy-α-D-arabino-hexopyranoside 
• 16718-95-9 methyl 4,6-O-benzylidene-2-deoxy-α-D-altropyranoside 
• 100-52-7 benzaldehyde 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 111375-91-8 Benzoic acid (2R,3R,4R,6S)-6-methoxy-2-methyl-4-trifluoromethanesulfonyloxy-tetrahydro-pyran-3-yl ester 
• 83497-33-0 methyl 4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-ribo-hexopyranoside 

Downstream Products

• 104652-07-5 methyl 4-O-(3,4-di-O-benzoyl-2,6-dideoxy-β-D-ribopyranosyl)-3-O-benzoyl-2,6-dideoxy-α-D-ribo-hexopyranoside 
• 104652-08-6 methyl 4-O-(3,4-di-O-benzoyl-2,6-dideoxy-α-D-ribopyranosyl)-3-O-benzoyl-2,6-dideoxy-α-D-ribo-hexopyranoside 
• 123077-03-2 methyl 3-O-benzoyl-2,6-dideoxy-α-D-erythro-hexopyranosid-4-ulose 
• 123098-99-7 methyl 3-O-benzoyl-2,6-dideoxy-α-D-erythro-hexopyranosid-4-ulose (p-tolylsulfonyl)hydrazone 
• 123077-04-3 methyl 3-O-benzoyl-2,3,6-trideoxy-4-<2-(p-tolylsulfonyl)hydrazino>-α-D-ribo-hexopyranoside 

Relevant articles and documents

Insights into the branched-chain formation of mycarose: Methylation catalyzed by an (S)-adenosylmethionine-dependent methyltransferase

A C-methyltransferase involved in methyl-branch formation in sugars has been characterized for the first time. TylC3, an (S)-adenosylmethylthionine(AdoMet)dependent enzyme, catalyzes the attachment of a methyl branch [Eq. (1)] in the biosynthesis of L-myc

Studies of the Mechanistic Diversity of Sodium Cyanoborohydride Reduction of Tosylhydrazones

Reduction of tosylhydrazone derivatives of ketones and aldehydes with sodium cyanoborohydride in acidic medium is a mild, albeit versatile, deoxygenation reaction.The reaction mechanism has been proposed to proceed via either a direct hydride attack route or a tautomerization-then-reduction route.By using a mild reduction procedure (NaBH3CN, THF-MeOH, 0 deg C), it has been possible to stop the deoxygenation halfway and isolate the nascent tosylhydrazine product.Characterization of the resulting hydrazine to define the origin of the hydrogen being delivered to theformer carbonyl carbon has allowed us to unambiguously distinguish between these two possible mechanisms.Studies of reduction of tosylhydrazones derived from conjugated and saturated ketones confirmed earlier speculation that these reductions occur through a direct hydride attack mechanism.The reduction of para-substituted methyl phenyl ketone tosylhydrazones revealed a competition between these two mechanisms.Substrates bearing electron-donating substituents prefer to direct hydride attack pathway, while those with electron-withdrawing substituents favor an initial tautomerization prior to reduction.Sugar and hydroxyl ketone tosylhydrazones are also reduced by competing mechanisms.The mechanistic diversity in those cases may be attributed to the inductive effects compelled by the α substituents and the conformational constraints imposed by the ring structure.The mechanistic insights gained from these studies indicate that the direct hydride attack mechanism is the main reaction pathway due to the propensity of NaBH3CN to selectively attack the iminium ion.The tautomerization-then-reduction mechanism prevails only when the tautomerization of hydrazon to azohydrazine is facilitated.