194347-75-6

Upstream product

• 108-24-7 acetic anhydride 
• 100-39-0 benzyl bromide 
• 194347-74-5 methyl 4-O-benzoyl-1-thio-α-L-rhamnopyranoside 
• 98-88-4 benzoyl chloride 
• 115678-10-9 methyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside 
• 615541-07-6 methyl 4-O-benzoyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside 
• 101068-98-8 methyl 2-O-acetyl-4-O-benzoyl-α-L-rhamnopyranoside 
• 14917-55-6 methyl 6-deoxy-α-L-mannopyranoside 
• 406460-55-7 methyl 2-O-acetyl-4-O-benzoyl-3-O-benzyl-α-L-rhamnopyranoside 
• 406460-49-9 methyl 2,3-O-methylorthoacetyl-α-L-rhamnopyranoside 
• 3908-55-2 Trimethyl(methylthio)silane 
• 406460-58-0 1,2-di-O-acetyl-4-O-benzoyl-3-O-benzyl-α-L-rhamnopyranose 

Downstream Products

• 194347-73-4 Benzoic acid (2S,3S,4R,6S)-4-benzyloxy-6-bromo-2-methyl-5-oxo-tetrahydro-pyran-3-yl ester 
• 406460-75-1 methyl (4-O-benzoyl-3-O-benzyl-2-O-acetyl-α-L-rhamnopyranosyl)-(1->4)-2,3-di-O-benzyl-α-D-galactopyranuronate trichloroacetimidate 
• 406460-74-0 methyl (4-O-benzoyl-3-O-benzyl-2-O-acetyl-α-L-rhamnopyranosyl)-(1->4)-2,3-di-O-benzyl-α-D-galactopyranuronate 
• 406460-62-6 2-O-acetyl-4-O-benzoyl-3-O-benzyl-α-L-rhamnopyranosyl trichloroacetimidate 
• 311350-24-0 methyl (2-O-acetyl-4-O-benzoyl-3-O-benzyl-α-L-rhamnopyranosyl)-(1->4)-(allyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate 
• 615541-33-8 Benzoic acid (2S,3S,4R,5R,6R)-5-acetoxy-6-((2S,3R,4S,5R,6R)-4,5-dihydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yloxy)-2-methyl-4-((2S,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester 
• 615541-31-6 methyl 2,3-O-isopropylidene-4-O-[2-O-acetyl-4-O-benzoyl-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-β-L-rhamnopyranosyl]-α-L-rhamnopyranoside 
• 615541-28-1 methyl 2,3-O-isopropylidene-4-O-(2-O-acetyl-4-O-benzoyl-3-O-benzyl-β-L-rhamnopyranosyl)-α-L-rhamnopyranoside 
• 615541-26-9 methyl 2,3-O-isopropylidene-4-O-(4-O-benzoyl-3-O-benzyl-β-L-rhamnopyranosyl)-α-L-rhamnopyranoside 
• 615541-30-5 methyl 2,3-O-isopropylidene-4-O-(2-O-acetyl-4-O-benzoyl-β-L-rhamnopyranosyl)-α-L-rhamnopyranoside 
• 194347-82-5 isopropyl 4-O-benzoyl-3-O-benzyl-6-deoxy-β-L-arabino-hexopyranosid-2-ulose 
• 194347-79-0 2-O-acetyl-1,5-anhydro-4-O-benzoyl-3-O-benzyl-6-deoxy-L-arabino-hex-1-enitol 
• 615541-10-1 Benzoic acid (2S,3aR,5S,6S,7R,7aR)-7-benzyloxy-2-methoxy-2,5-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6-yl ester 

Relevant academic research and scientific papers

Efficient generation of β-L-rhamnosidic linkages by the 2-ulosyl donor approach: Synthesis of a trisaccharide with a central β-L-rhamnose unit

Practical procedures for the production of variously blocked 6-deoxy-α-L-arabino-2-ketohexosyl bromides from L-rhamnose have been developed. These compounds are highly useful as indirect β-L-rhamnosyl donors: they undergo β-specific glycosidations under Koenigs-Knorr conditions, and the 2-keto group of the resulting 6-deoxy-β-L-hexosiduloses is reduced with high β-L-rhamno selectivity. The straightforward application of this 2-ulosyl donor approach for the synthesis of β-L-rhamnose-containing di- and trisaccharides is demonstrated. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).

Block synthesis with galacturonate trichloroacetimidates

The disaccharide methyl (4-O-benzoyl-3-O-benzyl-2-O-acetyl-α-L-rhamno pyranosyl)-(1→4)-(allyl 2,3-di-O-benzy-β-D-galactopyranosid)uronate (13) was obtained in an excellent yield of 88% using methyl (allyl 2,3-di-O-benzyl-β-D-galactopyranosid)uronate (12) as the glycosyl acceptor and a slight excess of the 1,2-di-O-acetyl-rhamnoglycosyl donor 5a. Disaccharide 13 is a key intermediate that can be used either as a glycosyl acceptor or glycosyl donor for the preparation of rhamnogalacturonan fragments. Here, introduction of the trichloroacetimidate function at the anomeric center gave the disaccharide glycosyl donor 28, which could be applied in a blockwise glycosylation reaction to form the L-Rha-α(1→4)-D-GalA-α(1→4)-D-GalA trisaccharide 29. Generally, on condition that no neighboring group effect influenced the reaction at the anomeric center of the α-trichloroacetimidate galacturonate glycosyl donors (20-22,28), α-glycosidic linkages were nearly exclusively formed, except in the case of the 4-O-methylgalactopyranosyluronate 22.

Efficient generation of β-L-rhamnosidic linkages via the ulosyl bromide approach

Practical protocols have been developed for the acquisition of ulosyl bromides of type III from L-rhamnose, i.e. 6-deoxy-α-L-arabino-2-ketohexosyl bromides 6-8. They have high potential as indirect β-L-rhamnosyl donors, as they undergo β-specific glycosid