158570-84-4

Upstream product

• 4132-28-9 2,3,4,6-tetra-O-benzyl-α-D-galactopyranose 
• 6386-24-9 2,3,4,6-tetra-O-benzyl-D-galactopyranose 
• 100-39-0 benzyl bromide 
• 3396-99-4 methyl α-D-galactopyranoside 
• 53008-63-2 methyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranoside 
• 100-44-7 benzyl chloride 

Downstream Products

• 158535-90-1 1,3,4,5-Tetra-O-benzyl-6-O-(tert-butyldimethylsilyl)-L-galactitol 
• 165881-13-0 2,3,4,6-tetra-O-benzyl-1-O-trityl-D-galactitol 
• 441771-42-2 2,3,4,6-tetra-O-benzyl-1,5-di-O-mesyl-D-galactitol 
• 1376554-96-9 (2R,3R,4S,5R,6S)-2-chloro-3,4,5-tris(benzyloxy)-6-benzyloxymethyltetrahydrothiopyran 1,1-dioxide 
• 1376554-75-4 (2S,3R,4R,5R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)tetrahydro-2H-thiopyran 
• 402475-59-6 ((1S,2R,3S)-4-(benzyloxymethyl)cycylopent-4-ene-1,2,3-triyl)tris(oxy)tris(methylene)tribenzene 
• 441061-42-3 (2S,3S,4R,5S)-1-butyl-3,4,5-tris(phenylmethoxy)-2-[(phenylmethoxy)methyl]piperidine 
• 441061-44-5 (2S,3S,4R,5S)-1-butyl-2-(hydroxymethyl)piperidine-3,4,5-triol 
• 930113-63-6 2,3,4,6-tetra-O-benzyl-D-arabinohexos-5-ulose 
• 131379-12-9 1,3,4,5-Tetra-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-O-(methoxymethyl)-L-galactitol 
• 931397-87-4 phosphoric acid dibenzyl ester 2,3,4,5,6-pentakis-benzyloxy-hexyl ester 
• 931397-80-7 2,3,4,5,6-penta-O-benzyl-1-O-tert-butyldimethylsilyl-D-galactitol 
• 931397-84-1 2,3,4,5,6-penta-O-benzyl-D-galactitol 
• 944417-17-8 (2S,3S,4S)-2,3,4-tribenzyloxy-5-((benzyloxy)methyl)-5-hexenal 

Relevant academic research and scientific papers

Pharmaceutically active piperidine derivatives

Compounds of formula (I): wherein R represents various substituent groups, are useful as inhibitors of glucosylceramide synthase.

Stereocontrolled formation of protected aminodeoxyalditols from simple carbohydrate precursors by debenzylating cycloetherification

A new and highly efficient methodology for the stereocontrolled synthesis of aminodeoxyalditols is described through a dimesylation/intramolecular SN2 nucleophilic substitution ringforming reaction sequence from glucose, mannose, and galactose derivatives

A potent bicyclic inhibitor of a family 27 α-galactosidase

Two isomeric bicyclo4.1.0heptane analogues of the glycosidase inhibitor galacto-validamine, (1R*,2S,3S,4S,5S,6S*)-5-amino-1-(hydroxymethyl) bicyclo4.1.0heptane-2,3,4-triol, have been synthesized in 13 steps from 2,3,4,6-tetra-O-benzyl-d-galactose. The inh

Synthesis and analysis of substrate analogues for UDP-galactopyranose mutase: Implication for an oxocarbenium ion intermediate in the catalytic mechanism

(Chemical Equation Presented) UDP-D-galactofuranose (2), which is essential for both cell growth and virulence in many pathogenic microorganisms, is converted from UDP-D-galactopyranose (UDP-Galp, 1) by the flavin adenine dinucleotide (FAD)-dependent enzyme UDP-galactopyranose mutase (UGM). Here, we report the synthesis of UDP-GalOH (13) and show it as an inhibitor for UGM with a binding affinity similar to that of 1. These results are more consistent with a mechanism involving an oxocarbenium ion intermediate in UGM catalysis.

Diastereoselectivity of the cyclization of hexos-5-uloses by Sm2-mediated pinacol coupling

2,3,4,6-Tera-O-benzyl-hexos-5-uloses derived from D-glucose, D- mannose and D-galactose have been cyclized to cis-diols by a one pot Swerm oxidation/SmI2-mediated pinacol coupling procedure. The effect of the substituent orientation on the diastereoselectivity of the coupling step is examined.

Synthesis of Protected Carbohydrate Derivatives through Homologation of Threose and Erythrose Derivatives with Chiral γ-Alkoxy Allylic Stannanes

Additions of the γ-alkoxy allylic stannanes (S)-1 and (R)-1 and the racemate (RS)-1 to the threose and erythrose aldehyde derivatives 6 and 15 in the presence of BF3*OEt2 or MgBr2*OEt2 were examined in order to establish stereochemical preferences.It was found that (S)-1 and aldehyde 6 afforded the syn,anti,syn adduct 7 in the BF3-promoted reaction, while (R)-1 and 6 gave the syn,syn,syn adduct 8 under MgBr2 conditions.Likewise, (S)-1 and aldehyde 15 yielded the syn,anti,anti adduct 16 with BF3, whereas (R)-1 and 15 led to the syn,syn,anti adduct 17 with MgBr2.The MgBr2-promoted reactions showed sufficient rate differences between the matched and mismatched stannanes to allow the use of racemic stannane (RS)-1 in just over 2-fold excess, whereupon the matched adducts 8 and 17 were favored by greater than 9:1 over the mismatched adducts.The major adducts 7, 8, 16, and 17 were converted to the hexose derivatives 21, 30/31, 34, and 39 by ozonolysis, selective deprotection, and refunctionalization.Adducts 16 and 17 were dihydroxylated with OsO4-NMO to the deoxyoctose precursors 40/41 and 42/43.