61199-73-3

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 14917-55-6 methyl 6-deoxy-α-L-mannopyranoside 

Downstream Products

• 70717-87-2 1,5-anhydro-1,2,6-trideoxy-3-C-methyl-L-ribo-hex-1-enitol 
• 70717-87-2 1,5-anhydro-1,2,6-trideoxy-3-C-methyl-L-ribo-hex-1-enitol 
• 98-85-1 1-Phenylethanol 
• 64880-43-9 methyl 2-O-benzoyl-3-bromo-3,6-dideoxy-α-L-altropyranoside 
• 105265-74-5 tert-Butyl-((3aR,4R,6S,7S,7aS)-4-methoxy-6-methyl-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy)-dimethyl-silane 
• 108782-77-0 methyl 2,3-O-benzylidene-4-O-trichloroacetimidoyl-α-L-rhamnopyranoside 
• 1002757-17-6 methyl 2,3-O-benzylidene-6-deoxy-4-O-(methoxymethyl)-α-L-mannopyranoside 
• 23089-58-9 N-acetyl-L-ristosamine 
• 119824-72-5 C₂₁H₂₁⁽²⁾HO₆ 
• 129090-79-5 C₂₁H₁₉⁽²⁾HBr₂O₆ 
• 108782-79-2 methyl 2,4-di-O-benzoyl-3,6-dideoxy-3-trichloroacetamido-α-L-altropyranoside 
• 108782-78-1 methyl 3-amino-2-O-benzoyl-3,6-dideoxy-α-L-altropyranoside 3N,4O-trichloroacetimidate 
• 263327-90-8 methyl 2,3,6-trideoxy-3-C-methyl-4-O-(4-nitrobenzoyl)-α-L-threo-hex-2-enopyranoside 
• 37091-13-7 Methyl-4-O-benzoyl-3-(benzoylamino)-2,3,6-tridesoxy-3-C-methyl-α-L-lyxo-hexopyranosid 

Relevant academic research and scientific papers

Synthesis of marmycin A and investigation into its cellular activity

Anthracyclines such as doxorubicin are used extensively in the treatment of cancers. Anthraquinone-related angucyclines also exhibit antiproliferative properties and have been proposed to operate via similar mechanisms, including direct genome targeting.

SYNTHESIS OF STEREOSPECIFICALLY LABELED CARBOHYDRATES: PREPARATION OF (3S)- AND (3R)-ASCARYLOSE

The general problem of the synthesis of 3,6-dideoxy sugars containing stereospecifically labeled hydrogen isotope at C-3 is adressed for the specific case of ascarylose (3,6-dideoxy-L-arabino-hexose).

Dioxolanylium Ions Derived from Carbohydrates. XI. Aminosugar Formation by trans Opening with the Trichloroacetimidoyl Neighbouring Group

A variety of benzylidene sugars containing vicinal trichloroacetimidoyl groups have been oxidized by N-bromosuccinimide, to ascertain which structural features are necessary for neighbouring group participation from the iminoester in the opening of the transitory benzoxonium ion.The results indicate that the trichloroacetimidoyl group closely resembles the acyl group in its ability to participate, and that the resulting iminoester is strongly favoured compared to the benzoxonium ion.The outcome of the reaction in these cases is therefore a clean, regiospecific introduction of an amino group into the carbohydrate molecule.

Reaction of derivatives of methyl 2,3-O-benzylidene-6-deoxy-alpha-L-mannopyranoside with butyllithium: synthesis of methyl 2,6-dideoxy-4-O-methyl-alpha-L-erythro-hexopyranosid-3-ulose.

Methyl 2,3-O-benzylidene-6-deoxy-alpha-L-mannopyranoside (2) reacted with butyllithium to give a mixture of 1,5-anhydro-3-C-butyl-1,2,6-trideoxy-L-ribo-hex-1-enitol (3) and its L-arabino analogue (4), together with methyl 2,3,6-trideoxy-alpha-L-erythro-hex-2-enopyranoside (5). In contrast, the 4-O-methyl-analogue (8) of 2 was converted by butyllithium into methyl 2,6-dideoxy-4-O-methyl-alpha-L-erythro-hexo-pyranosid-3-ulose (9), which was further characterized as its oxime 10. The 4-O-benzyl analogue of 8, obtained as two separate diastereoisomers (6 and 7) differing in configuration at C-2 of the dioxolane ring gave a complex misture of products on treatment with butyllithium.