25019-68-5

Upstream product

• 100-39-0 benzyl bromide 
• 14133-63-2 methyl 2,3-O-isopropylidene-α-L-rhamnoside 
• 100-44-7 benzyl chloride 
• 77-76-9 2,2-dimethoxy-propane 
• 14917-55-6 methyl 6-deoxy-α-L-mannopyranoside 
• 73-34-7 L-rhamnose 

Downstream Products

• 25019-69-6 methyl 4-O-benzyl-α-L-rhamnopyranoside 
• 98928-08-6 methyl 4-O-benzyl-2-O-isopropyl-α-L-rhamnopyranoside 
• 98928-09-7 methyl 4-O-benzyl-3-O-isopropyl-α-L-rhamnopyranoside 
• 131337-88-7 methyl 2-O-allyl-3,4-di-O-benzyl-α-L-rhamnopyranoside 
• 69558-08-3 methyl 2-O-allyl-4-O-benzyl-α-L-rhamnopyranoside 
• 69558-09-4 methyl 3-O-allyl-4-O-benzyl-α-L-rhamnopyranoside 
• 130851-52-4 methyl 4-O-benzyl-3-O-methyl-2-O-pivaloyl-α-L-rhamnopyranoside 
• 90670-49-8 tert-Butyl-((2S,3S,4S)-4-methoxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-dimethyl-silane 
• 55053-28-6 Methyl 4-O-benzyl-2,6-dideoxy-3-O-methyl-α-L-arabinohexopyranosid 
• 69558-13-0 methyl 4-O-benzyl-3-O-methyl-α-L-rhamnopyranoside 

Relevant academic research and scientific papers

Induction of a preferred sense of twist in flexible diphenyls by carbohydrate scaffolds. Synthesis of two "naked" ellagitannin analogous

The synthesis of "naked" ellagitannin analogues 1 and 2, having a preferred sense of twist of the diphenyl moiety, with a rhamnose and a glucose template, is reported. A clear induction in the chirality of the diphenyl moiety, mediated through a 10-membered ring via ester linkages, was observed. The chiral scaffold of glucose (diequatorial 2,3-hydroxyl groups) exerts a remarkable stronger atropdiastereoselective effect onto the diphenoyl group than the rhamnose ring (axial-equatorial 2,3-hydroxyl groups), according to the Schmidt-Haslam hypothesis.

Synthesis of methyl 3-O--α-L-rhamnopyranoside, a trisaccharide related to the Klebsiella type 9 antigen

The trisaccharide related to the polysaccharide from Klebsiella type 9 namely methyl 3-O--α-L-rhamnopyranoside (12) has been synthesised in 11 steps from the constituent sugars.

Reactions of Partially Acylated Aldehexopyranosides, VIII. A New Synthesis of the Tetradeoxydisaccharide in Avermectins

Methyl 4-O-benzyl-3-O-methyl-2-O-pivaloyl-α-L-rhamnopyranoside (6) was prepared from L-rhamnose in an improved synthesis in six steps (overall yield: 51percent) and was used as the key building block.Acetolysis of 6 gave the glycosyl donor, 1,4-di-O-acetyl-3-O-methyl-2-O-pivaloyl-α-L-rhamnopyranose (7), which was coupled with the acceptor, methyl 3-O-methyl-2-O-pivaloyl-α-L-rhamnopyranoside (8), simply prepared by debenzylation of 6.The glycosylation reaction was carried out in the presence of trimethylsilyl triflate and led exclusively to the α-linked disaccharide, methyl 4-O-(4-O-acetyl-3-O-methyl-2-O-pivaloyl-α-L-rhamnopyranosyl) -3-O-methyl-2-O-pivaloyl-α-L-rhamnopyranopside (9).Selective removal of the acetate group and irradiation of the 2,2'-dipivaloates gave directly the tetradeoxydisaccharide, methyl 4-O-(α-L-oleandrosyl)-α-L-oleandropyranoside (11).Irradiation of compound 8 afforded methyl α-L-oleandropyranoside (12) as the only product in 80percent yield.Key Words: Avermectins / Methyl 4-O-(α-L-oleandrosyl)-α-L-oleandropyranoside / Photochemical deoxygenation / Glycosylation

Synthesis of disaccharide methyl glycosides related to the polysaccharide from Klebsiella serotype 40 and a study of their inhibition in the precipitin reaction.

The methyl glycosides of alpha-D-Manp-(1----4)-alpha-L-Rhap (3), alpha-L-Rhap-(1----3)-beta-D-Galp (4), beta-L-Rhap-(1----3)-beta-D-Galp (5), beta-D-Galp-(1----2)-alpha-L-Rhap (6), and beta-D-GlcpA-(1----2)-alpha-L-Rhap (7) have been synthesised and their

Practical synthesis of oligosaccharides. Partial synthesis of avermectin B(1a)

A practical synthesis of oligosaccharides from phenylthio sugars via glycosyl fluorides is described. The new technology is applied to the synthesis of hexasaccharide 9 from a glucose derivative and avermectin B1a(11) from an avermectin B1

Preparation of Some Partially Methylated L-Rhamnosides and D-Ribosides

Partially methylated L-rhamnosides and D-ribosides have been prepared using limited amounts (25 to 35percent less than that needed for complete methylation) of methylating reagents, and characterized by GLC or GLC/MS.Methyl 2,3-di-O-methyl-α-L-rhamnoside has also been prepared by a modified method of Hough and Jones .