59055-57-1

Upstream product

• 67-56-1 methanol 
• 86795-39-3 (2S,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-chloro-6-methyltetrahydro-2H-pyran 
• 100-44-7 benzyl chloride 
• 14917-55-6 methyl 6-deoxy-α-L-mannopyranoside 
• 80152-99-4 1-O-acetyl-2,3,4-tri-O-benzyl-6-deoxy-α-L-mannose 
• 210426-02-1 2,3,4-tri-O-benzyl-L-rhamnopyranose 
• 100-39-0 benzyl bromide 
• 65518-53-8 methyl 2,3,4-tri-O-benzyl-6-O-tosyl-α-D-mannopyranoside 
• 34212-64-1 methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 51842-18-3 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 291753-79-2 methyl 2,3,4-tri-O-benzyl-6-deoxy-6-iodo-α-D-manno-pyranoside 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 131089-34-4 3-O-benzoyl-6-O-(t-butyldiphenyl)silyl-α-D-mannopyranoside 
• 186540-03-4 tert-Butyl-diphenyl-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-silane 

Downstream Products

• 59055-58-2 2,3,4-tri-O-benzyl-L-rhamnose 
• 86795-38-2 2,3,4-tri-O-(phenylmethyl)-α-L-rhamnopyranoside 
• 80152-99-4 1-O-acetyl-2,3,4-tri-O-benzyl-6-deoxy-α-L-mannose 
• 1361382-79-7 2,3,4-tri-O-benzyl-6-deoxy-α-D-mannopyranosyl (n-phenyl)trifluoroacetimidate 
• 15814-59-2 (2S,3S,4S,5S,6R)-2-methoxy-6-methyltetrahydro-2H-pyran-3,4,5-triol 
• 89401-16-1 2,3,4-tri-O-benzyl-β-D-rhamnopyranosyl α-L-rhamnopyranoside 
• 89401-16-1 2,3,4-tri-O-benzyl-α-D-rhamnopyranosyl α-L-rhamnopyranoside 
• 89401-15-0 2,3,4-tri-O-benzyl-β-D-rhamnopyranosyl 2,3,4-tri-O acetyl-α-L-rhamnopyranoside 
• 89401-15-0 2,3,4-tri-O-benzyl-α-D-rhamnopyranosyl 2,3,4-tri-O acetyl-α-L-rhamnopyranoside 
• 603962-00-1 2,3,4-tri-O-benzyl-α-D-rhamnopyranose 
• 210426-02-1 2,3,4-tri-O-benzyl-L-rhamnopyranose 
• 101304-92-1 2,3,4-tri-O-benzyl-L-rhamnosyl octanoate 
• 103368-09-8 2,3,4-tri-O-benzyl-β-L-rhamnopyranose 1-O-trichloroacetimidate 

Relevant academic research and scientific papers

Sugar-based micro/mesoporous hypercross-linked polymers with in situ embedded silver nanoparticles for catalytic reduction

Porous hypercross-linked polymers based on perbenzylated monosugars (SugPOP-1–3) have been synthesized by Friedel–Crafts reaction using formaldehyde dimethyl acetal as an external cross-linker. Three perbenzylated monosugars with similar chemical structur

BIARYL AMIDES WITH MODIFIED SUGAR GROUPS FOR TREATMENT OF DISEASES ASSOCIATED WITH HEAT SHOCK PROTEIN PATHWAY

Provided are biaryl amides and coumarin-based compounds with modified sugar groups for treatment of diseases associated with heat shock protein pathway. The compounds having the following formulas, wherein variables are as defined herein. Formulae (I), (II), (III), (IV), and (V), Pharmaceutical compositions of the compounds are also provided. These biaryl amides and coumarin-based derivatives with modified sugar groups are useful for treatment and prevention of diseases and disorders, including neurological disorders, such as neurodegenerative diseases and nerve damaging disorders, for example, diabetic peripheral neuropathy.

Mannose-binding geometry of pradimicin A

Pradimicins (PRMs) and benanomicins are the only family of non-peptidic natural products with lectin-like properties, that is, they recognize D-mannopyranoside (Man) in the presence of Ca2+ ions. Coupled with their unique Man binding ability, t

β-Rhamnosides from 6-thio mannosides

Upon condensation of 6-thio-6-deoxy-mannosyl donors 1,2-cis products are obtained with a high degree of stereoselectivity. Subsequent reductive removal of the 6-thio functionality gives 1,2-cis rhamnosides. The 1,2-cis-selectivity can be rationalized with

First synthesis of astilbin, biologically active glycosyl flavonoid isolated from Chinese folk medicine

A synthetic route to a biologically active glycosyl flavonoid, astilbin (1), was developed. The tetra-benzyl ether 4, derived from (+)-catechin, was glycosylated with the L-rhamnosyl donor 10 by using Cp2HfCl2-AgClO4, and subsequent oxidation of the C(4)position of the flavan skeleton followed by deprotection gave 1. (C) 2000 Elsevier Science Ltd.

α-Selective thermal glycosidation of rhamnosyl and mannosyl chlorides

Stereoselective thermal glycosylation of a variety of alcohols with 2,3,4-tri-O-benzylα-L-rhamnopyranosyl chloride and 2,3,4,6-tstra-O-benzyl-α-D-mannopyranosyl chloride have achieved to give α-glycosides in high selectivity.

Cardiac Glycosides. 7. Sugar Stereochemistry and Cardiac Glycoside Activity

Digitoxigenin α-L, β-L, α-D, and β-D-glucosides; α-L-, β-L-, α-D-, and β-D-mannosides; and α-L- and β-L-rhamnosides were stereoselectively synthetized from the corresponding sugar tetrabenzyl trichloroacetimidates.The Na+, K+-ATPase receptor inhibitory activities of these glycosides (as a measure of receptor binding) were compared with those digitoxigenin, digitoxigenin 6'-hydroxy-β-D-digitoxide, digitoxigenin β-D-galactoside, and digitoxigenin β-D-digitoxoside.The observed activities reveal that a given sugar substituent may have a role in bindingof some glycoside stereoisomers, but not others.With α-L- and possibly β-L-rhamnosides, the 5'-CH3 and 4'-OH appear to have a predominant role in binding to the N+, K+-ATPase receptor.Addition of a 6'-OH to form the corresponding mannosides dramatically disrupts the effect of both the 5'-CH3 and 4'-OH in prompting receptor binding of the α-L isomer.However, with the β-L isomer, some influence of 4'-OH, 3'-OH, and 2'-OH binding remains.With β-D-glycosides, binding via the "5'-CH3 site" appears to be of little importance and addition of a 6'-OH diminishes activity only slightly.With these β-D-glycosides, and equatorial 4'-OH, axial 3'-OH, and equatorial 2'-OH groups appear to contribute to binding.

Nuclear Magnetic Resonance Study on Glycolsyl Esters: Glycosyl Esters of 3-O-Acetyloleanolic Acid and Octanoic Acid

α-L-Rhamnosyl, α-L-arabinosyl, 2'-O-β-D-glucosyl-α-L-arabinosyl and 2'-O-α-L-rhamnosyl-α-L-arabinosyl esters of octanoic acid and β-D-xylosyl, α-L-rhamnosyl, α-L-arabinosyl, 2'-O-β-D-glucosyl-α-L-arabinosyl and 2'-O-α-L-rhamnosyl-α-L-arabinosyl esters of 3-O-acetyloleanolic acid were synthesized.The nuclear magnetic resonance spectra of sugar moieties of the esters of 3-O-acetyloleanolic acid, which is a represantative sterically hindered carboxylic acid, were compared with those of the corresponding less-hindered glycosyl esters of octanoic acid.In the case of rhamnose and arabinose, the displacements of sugar carbon signals on acylation of the anomeric hydroxyl group are similar to those already observed for fatty acid glucosyl esters regardless of the steric hindrance of the acyl group.However, the 2-O-glycosylation shifts of 1-O-acyl-α-L-arabinopyranose were found to depend upon the steric hindrance of the acyl groups.The anomalous 2'-O-glycosylation shifts of arabinosyl carbon signals of α-L-arabinosyl 3-O-acetyl-oleanolate were not observed in the case of α-L-arabinosyl octanoate.Keywords---- glycosyl ester synthesis; reducing terminal protecting group; tert-butyl glycoside; glycosyl octanoate; glycosyl 3-O-acetyloleanolate; NMR glycosylation shift; 1-O-acyl-2-O-glycosyl-α-L-arabinose NMR; 2-O-glycosyl-arabinopyranoside ring conformation.

SYNTHESIS OF (1->1)-BONDED RHAMNOPYRANOSYL-RHAMNOPYRANOSIDES CONTAINING L,L AND L,D BUILDING-STONES. HIGH-FIELD 1H- AND 13C-NMR SPECTROSCOPIC STUDIES ON THE CONFORMATION OF THE INTERGLYCOSIDIC BONDS

Rhamnosylation of 2,3,4-tri-O-acetyl-L- (1) and 2,3,4-tri-O-benzyl-D-rhamnopyranose (9) with α-acetobromo-L-rhamnose resulted in fully protected α-L, α-L-, α-L, β-L-, α-D,α-L-, and β-D,α-L-rhamnopyranosyl-rhamnopyranosides.The signal of the anomeric carbo