61199-76-6

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 14133-63-2 methyl 2,3-O-isopropylidene-α-L-rhamnoside 
• 14917-55-6 methyl 6-deoxy-α-L-mannopyranoside 
• 65475-58-3 methyl 4-O-acetyl-endo-2,3-O-benzylidene-α-L-rhamnopyranoside 
• 65529-48-8 methyl endo-2,3-O-benzylidene-α-L-rhamnopyranoside 
• 100-44-7 benzyl chloride 
• 25019-69-6 methyl 4-O-benzyl-α-L-rhamnopyranoside 

Downstream Products

• 5158-60-1 methyl 6-deoxy-3-O-methyl-α-L-mannopyranoside 
• 157889-68-4 2,4-di-O-benzyl-α-L-rhamnopyranoside 
• 69850-47-1 (2R,3R,4R,5R,6S)-3,5-Bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-ol 
• 69558-07-2 methyl-3,4-di-O-benzyl-α-L-rhamnopyranoside 
• 71348-34-0 methyl 3,4-di-O-benzyl-2-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside 
• 71348-35-1 methyl 2,4-di-O-benzyl-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside 
• 66320-16-9 methyl α-L-rhamnopyranosyl-(1->2)-α-L-rhamnopyranoside 

Relevant academic research and scientific papers

An n.m.r. and conformational analysis of the terminal trisaccharide from the serologically active glycolipid of Mycobacterium leprae in different solvents

The 1H- and 13C-n.m.r. spectra of allyl 2-O--3-O-methyl-α-L-rhamnopyranoside (3), a glycoside of the terminal trisaccharide found in the phenolic glycolipid I from Mycobacterium leprae, and those of the two component disaccharides, allyl 4-O-(3,6-di-O-methyl-β-D-glucopyranosyl)-2,3-di-O-methyl-α-L-rhamnopyranoside (1) and allyl 2-O-(2,3-di-O-methyl-α-L-rhamnopyranosyl)-3-O-methyl-α-L-rhamnopyranoside (2) have been assigned completely by 1D and 2D techniques.The preferred conformations, determined by chemical shift and n.O.e. studies, were different in D2O, CD3OD, and CDCl3.The preferred conformation of 3 accorded with the results of hard-sphere exo-anomeric (HSEA) calculations.

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.