73111-58-7

Upstream product

• 73111-12-3 methyl tri-O-benzyl-6-bromo-β-D-6-deoxy-glucopyranoside 
• 114219-26-0 methyl 2,3,4-tri-O-benzyl-6-O-(4-methylbenzenesulfonyl)-α-D-glucopyranoside 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 7177-79-9 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 85716-43-4 methyl 6-deoxy-6-iodo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 291753-79-2 methyl 2,3,4-tri-O-benzyl-6-deoxy-6-iodo-α-D-manno-pyranoside 
• 7177-79-9 methyl 2,3-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 166592-73-0 methyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside 
• 63734-12-3 methyl 6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside 
• 108713-90-2 2,3,4-tri-O-benzyl-D-xylose diethyl dithioacetal 
• 116384-32-8 2,3,4-tri-O-benzyl-D-xylo-pentodialdose 1,1-diethyl dithioacetal 
• 97-30-3 methyl-alpha-D-glucopyranoside 

Downstream Products

• 73174-45-5 (2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-methoxy-6-methyltetrahydro-2H-pyran 
• 138560-26-6 6,7-dideoxy-2-<(4-methoxyphenyl)methoxy>-3,4,5-tris-O-(phenylmethyl)-D-gulo/ido-hept-6-enose, cyclic 1,3-propanediyl mercaptals 
• 219586-93-3 2,3,4-Tri-O-benzyl-5,6-dideoxy-D-xylo-hex-5-enose oxime 
• 343934-66-7 (2S,3S,4R)-2,3,4-tribenzyloxy-hex-5-ene-1-al 4-bromophenylhydrazone 
• 371146-18-8 (3S,4S,5S,6R)-4,5,6-Tris-benzyloxy-2,2-difluoro-3-hydroxy-oct-7-enoic acid ethyl ester 
• 371146-14-4 (3R,4S,5S,6R)-4,5,6-Tris-benzyloxy-2,2-difluoro-3-hydroxy-oct-7-enoic acid ethyl ester 
• 495397-82-5 ethyl (4R,5S,6R)-4,5,6-tribenzyloxy-3-oxo-7-octenoate 
• 844901-88-8 methyl (2E,4S,5S,6R)-4,5,6-tri(benzyloxy)-2,7-octadienoate 
• 910033-61-3 N-((2S,3S,4R)-2,3,4-Tris-benzyloxy-hex-5-enyl)-hydroxylamine 
• 157761-58-5 ((1R,2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-7-oxabicyclo-[4.1.0]heptan-2-yl)methanol (+)-2,3,4-tri-O-benzylcyclophellitol 
• 176380-10-2 (1R,2R,5S,6S)-5,6-bis(benzyloxy)-2-{[(tert-butyldimethylsilyl)-oxy]methyl}cyclohex-3-en-1-ol 
• 622832-75-1 Formic acid (1R,4S,5R,6R)-4,5,6-tris-benzyloxy-cyclohex-2-enylmethyl ester 

Relevant academic research and scientific papers

Structure–Activity Studies of N-Butyl-1-deoxynojirimycin (NB-DNJ) Analogues: Discovery of Potent and Selective Aminocyclopentitol Inhibitors of GBA1 and GBA2

Analogues of N-butyl-1-deoxynojirimycin (NB-DNJ) were prepared and assayed for inhibition of ceramide-specific glucosyltransferase (CGT), non-lysosomal β-glucosidase 2 (GBA2) and the lysosomal β-glucosidase 1 (GBA1). Compounds 5 a–6 f, which carry sterically demanding nitrogen substituents, and compound 13, devoid of the C3 and C5 hydroxy groups present in DNJ/NB-DGJ (N-butyldeoxygalactojirimycin) showed no inhibitory activity for CGT or GBA2. Inversion of stereochemistry at C4 of N-(n-butyl)- and N-(n-nonyl)-DGJ (compounds 24) also led to a loss of activity in these assays. The aminocyclopentitols N-(n-butyl)- (35 a), N-(n-nonyl)-4-amino-5-(hydroxymethyl)cyclopentane- (35 b), and N-(1-(pentyloxy)methyl)adamantan-1-yl)-1,2,3-triol (35 f), were found to be selective inhibitors of GBA1 and GBA2 that did not inhibit CGT (>1 mm), with the exception of 35 f, which inhibited CGT with an IC50 value of 1 mm. The N-butyl analogue 35 a was 100-fold selective for inhibiting GBA1 over GBA2 (Ki values of 32 nm and 3.3 μm for GBA1 and GBA2, respectively). The N-nonyl analogue 35 b displayed a Ki value of ?14 nm for GBA1 inhibition and a Ki of 43 nm for GBA2. The N-(1-(pentyloxy)methyl)adamantan-1-yl) derivative 35 f had Ki values of ≈16 and 14 nm for GBA1 and GBA2, respectively. The related N-bis-substituted aminocyclopentitols were found to be significantly less potent inhibitors than their mono-substituted analogues. The aminocyclopentitol scaffold should hold promise for further inhibitor development.

Synthesis of polyhydroxylated decalins via two consecutive one-pot reactions: 1,4-Addition/aldol reaction followed by RCM/syn-dihydroxylation

Synthesis of novel polyhydroxylated derivatives of decalin is described. The presented methodology consists in a one-pot copper-catalyzed 1,4-addition of vinylmagnesium bromide to sugar-derived cyclohexenone, followed by an aldol reaction with a derivativ

Stereoselective and regioselective one-pot synthesis of polyhydroxy bicyclic diazenes and hydrazones from methyl 6-deoxy-6-iodo-hexosides

An efficient, stereoselective, and base-controlled procedure for the preparation of polyhydroxy bicyclic diazenes and polyhydroxy bicyclic hydrazones is described, starting from sugar-derived methyl 6-deoxy-6-iodo-hexosides. The one-pot synthesis involves

Stable analogues of nojirimycin-synthesis and biological evaluation of nojiristegine and manno-nojiristegine

Two novel iminosugars called nojiristegines, being structural hybrids between nor-tropane alkaloid calystegine and nojirimycins, have been synthesised and found to be stable molecules despite the presence of a hemiaminal functionality. The synthesised iminosugars were evaluated against a panel of glycosidases and the best inhibition (IC50), found against α-glucosidases, was in the micromolar region. The compounds were also evaluated as potential antibiotics but no useful level of activity was observed.

Synthesis and evaluation of eight- and four-membered iminosugar analogues as inhibitors of testicular ceramide-specific glucosyltransferase, testicular β-glucosidase 2, and other glycosidases

Eight- and four-membered analogues of N-butyldeoxynojirimycin (NB-DNJ), a reversible male contraceptive in mice, were prepared and tested. A chiral pool approach was used for the synthesis of the target compounds. Key steps for the synthesis of the eight-membered analogues involve ring-closing metathesis and Sharpless asymmetric dihydroxylation and for the four-membered analogues Sharpless epoxidation, epoxide ring-opening (azide), and Mitsunobu reaction to form the four-membered ring. (3S,4R,5S,6R,7R)-1-Nonylazocane-3,4,5,6,7-pentaol (6) was moderately active against rat-derived ceramide-specific glucosyltransferase, and four of the other eight-membered analogues were weakly active against rat-derived β-glucosidase 2. Among the four-membered analogues, ((2R,3S,4S)-3-hydroxy-1-nonylazetidine-2,4-diyl)dimethanol (25) displayed selective inhibitory activity against mouse-derived ceramide-specific glucosyltransferase and was about half as potent as NB-DNJ against the rat-derived enzyme. ((2S,4S)-3-Hydroxy-1-nonylazetidine-2,4-diyl)dimethanol (27) was found to be a selective inhibitor of β-glucosidase 2, with potency similar to NB-DNJ. Additional glycosidase assays were performed to identify potential other therapeutic applications. The eight-membered iminosugars exhibited specificity for almond-derived β-glucosidase, and the 1-nonylazetidine 25 inhibited α-glucosidase (Saccharomyces cerevisiae) with an IC50 of 600 nM and β-glucosidase (almond) with an IC50 of 20 μM. Only N-nonyl derivatives were active, emphasizing the importance of a long lipophilic side chain for inhibitory activity of the analogues studied.

Stereoselective synthesis of polyoxygenated linear diaza-triquinanes via intramolecular 1,3-dipolar cycloaddition of sugar-derived hex-5-enals

An efficient and stereoselective synthesis of diaza-triquinanes, the skeleton structures of many natural products, has been accomplished by intramolecular 1,3-dipolar cycloaddition of azomethine imine generated from sugar-derived hex-5-enal and pyrazolidi

Straightforward synthesis of diverse 1-deoxyazapyranosides via stereocontrolled nucleophilic additions to six-membered cyclic nitrones

A systematic study of diastereoselective nucleophilic addition of Grignard reagents to six-membered chiral tri-O-benzyl cyclic nitrones is described. With all eight chiral cyclic nitrones and asymmetric reaction conditions in hand, a practical methodology is established for the preparation of diverse 1-deoxyazapyranosides bearing various stereogenic centers. We have developed practical methods to prepare all eight six-membered chiral cyclic nitrones. Using these cyclic nitrones and diastereoselective nucleophilic additions, 12 examples of diverse 1-deoxyazapyranosides including enantiomers were synthesized to demonstrate the generality and flexibility of this new approach.

A concise synthesis of castanospermine by the use of a transannular cyclization

(Chemical Equation Presented) A nine-step synthesis of (+)-castanospermine has been accomplished in 22% overall yield from methyl α-D- glucopyranoside. The key transformations involve a zinc-mediated fragmentation of benzyl-protected methyl 6-iodoglucopyr

An intramolecular 1,3-dipolar cycloaddition reaction towards the synthesis of chiral azetidine nucleoside analogues: The D-gluco case

The diastereoselective intramolecular 1,3-dipolar cycloaddition reaction of unsaturated nitrones, derived from methyl α-D-glucopyranoside with 2-furaldehyde and 2-(benzyloxy)acetaldehyde has been studied. In our pevious studies with 2-furaldehyde, the cyc

Enantiodivergent formal synthesis of (+)-and (-)-cyclophellitol from D-xylose based on the latent symmetry concept

(Chemical Equation Presented) Formal synthesis of (+)- and (-)-cyclophellitol from D-xylose has been accomplished through utilization of the latent plane of chirality present in the starting carbohydrate. The synthetic pathway is suitable for preparation