61199-75-5

Upstream product

• 25019-69-6 methyl 4-O-benzyl-α-L-rhamnopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 65529-46-6 Methyl exo-2,3-di-O-benzylidene-α-L-rhamnopyranoside 
• 100-44-7 benzyl chloride 
• 65475-56-1 methyl 4-O-acetyl-exo-2,3-O-benzylidene-α-L-rhamnopyranoside 
• 14917-55-6 methyl 6-deoxy-α-L-mannopyranoside 

Downstream Products

• 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

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.