111476-62-1

Upstream product

• 100-39-0 benzyl bromide 
• 1707-77-3 1,2:5,6-di-O-isopropylidene-D-mannitol 
• 100-44-7 benzyl chloride 
• 69-65-8 mannitol 

Downstream Products

• 36199-02-7 3,4-di-O-benzyl-D-mannitol 
• 121964-05-4 3,4-di-O-benzyloxy-5,6-O-isopropylidene-D-mannitol 
• 222555-96-6 2,5-anhydro-3,4-di-O-benzyl-D-mannitol 
• 323580-67-2 (R)-4-((1R,2R)-1,2-Bis-benzyloxy-2-(S)-oxiranyl-ethyl)-2,2-dimethyl-[1,3]dioxolane 
• 323580-65-0 Acetic acid (2R,3R,4R)-3,4-bis-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-butyl ester 
• 111476-63-2 3,4-dibenzyloxy-1,2,5,6-tetra-O-mesyl-D-mannitol 
• 111555-72-7 R,R-3,4-dibenzyloxy-threo-hexa-1,5-diene 
• 553665-15-9 (4R,5R)-4,5-Bis-benzyloxy-hept-6-enoic acid (1S,2S)-1-allyl-2-(2-methoxy-ethoxymethoxy)-octyl ester 
• 553665-17-1 (E)-(5R,6R,10S)-5,6-Bis-benzyloxy-10-[(S)-1-(2-methoxy-ethoxymethoxy)-heptyl]-3,4,5,6,9,10-hexahydro-oxecin-2-one 
• 553664-97-4 (4R,5R)-4,5-bis(benzyloxy)hept-6-enoic acid 
• 863972-80-9 (4R,5S)-4,5-Bis-benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentanoic acid ethyl ester 
• 863972-81-0 (4R,5R,6R)-4,5-Bis-benzyloxy-6,7-dihydroxy-heptanoic acid ethyl ester 
• 863972-79-6 (E)-(4R,5S)-4,5-Bis-benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-2-enoic acid ethyl ester 
• 863972-82-1 (4R,5R)-4,5-Bis-benzyloxy-hept-6-enoic acid ethyl ester 

Relevant academic research and scientific papers

Simple and efficient synthesis of 2,5-anhydro-d-glucitol

The synthesis of 2,5-anhydro-d-glucitol is described via intramolecular cyclization of diepoxide using ammonium formate in MeOH by a microwave-assisted reaction. The overall yield was 32% from d-mannitol derivative involving seven steps.

L-DOPA AND/OR DOPA DECARBOXYLSE INHIBITORS CONJUGATED TO SUGAR FOR THE TREATMENT OF DOPAMINE-RESPONSIVE DISORDERS

The present invention provides conjugates comprising a sugar such as mannitol and one or more L-DOPA and/or DOPA decarboxylse inhibitors including, inter alia, L- DOPA, carbidopa, benserazide, or a combination thereof, wherein the sugar is conjugated to t

Iminosugars: Effects of stereochemistry, ring size, and n-substituents on glucosidase activities

N-substituted iminosugar analogues are potent inhibitors of glucosidases and glycosyltransferases with broad therapeutic applications, such as treatment of diabetes and Gaucher disease, immunosuppressive activities, and antibacterial and antiviral effects against HIV, HPV, hepatitis C, bovine diarrhea (BVDV), Ebola (EBOV) and Marburg viruses (MARV), influenza, Zika, and dengue virus. Based on our previous work on functionalized isomeric 1,5-dideoxy-1,5-imino-D-gulitol (L-gulo-piperidines, with inverted configuration at C-2 and C-5 in respect to glucose or deoxynojirimycin (DNJ)) and 1,6-dideoxy-1,6-imino-D-mannitol (D-manno-azepane derivatives) cores N-linked to different sites of glucopyranose units, we continue our studies on these alternative iminosugars bearing simple N-alkyl chains instead of glucose to understand if these easily accessed scaffolds could preserve the inhibition profile of the corresponding glucose-based N-alkyl derivatives as DNJ cores found in miglustat and miglitol drugs. Thus, a small library of iminosugars (14 compounds) displaying different stereochemistry, ring size, and N-substitutions was successfully synthesized from a common precursor, D-mannitol, by utilizing an SN2 aminocyclization reaction via two isomeric bis-epoxides. The evaluation of the prospective inhibitors on glucosidases revealed that merely D-gluco-piperidine (miglitol, 41a) and L-ido-azepane (41b) DNJ-derivatives bearing the N-hydroxylethyl group showed inhibition towards α-glucosidase with IC50 41 μM and 138 μM, respectively, using DNJ as reference (IC50 134 μM). On the other hand, β-glucosidase inhibition was achieved for glucose-inverted configuration (C-2 and C-5) derivatives, as novel L-gulo-piperidine (27a) and D-manno-azepane (27b), preserving the N-butyl chain, with IC50 109 and 184 μM, respectively, comparable to miglustat with the same N-butyl substituent (40a, IC50 172 μM). Interestingly, the seven-membered ring L-ido-azepane (40b) displayed near twice the activity (IC50 80 μM) of the corresponding D-gluco-piperidine miglustat drug (40a). Furthermore, besides α-glucosidase inhibition, both miglitol (41a) and L-ido-azepane (41b) proved to be the strongest β-glucosidase inhibitors of the series with IC50 of 4 μM.

Mannitol bis-phosphate based inhibitors of fructose 1,6-bisphosphate aldolases

Several 5-O-alkyl- and 5-C-alkyl-mannitol bis-phosphates were synthesized and comparatively assayed as inhibitors of fructose bis-phosphate aldolases (Fbas) from rabbit muscle (taken as surrogate model of the human enzyme) and from Trypanosoma brucei. A l

An efficient approach to 2,5-anhydro-glucitol-based 1′-homo-N- nucleoside mimetics

This Letter describes an efficient synthesis of a range of 1′-homo-N-nucleoside mimetics with a series of 4-substituted 1,2,3-triazoles replacing the natural nucleobase. The synthesis of 6-O-monosulfated 1′-homo-N-nucleoside mimetic derivatives is also discussed.

Stereoselective synthesis of 3-amino-3-deoxy-aldohexoses by aldol condensation of tricarbonyliron-α-Aminodienone complexes: Total synthesis of multiprotected kanosamine

An aldol reaction between the divalent tin enol ether of racemic N-Boc α-aminodienone-tricarbonyliron complex and multiprotected d-glyceraldehyde provided predominantly two enantiomerically pure ketol diastereoisomers. From there, multiprotected kanosamin

Total synthesis of (+)-aspicilin from D-mannitol

The total synthesis of the 18-membered lichen macrolide, (+)-aspicilin, has been accomplished utilizing the Swern oxidation, Masamune-Roush olefination, and ring-closing metathesis of a trienic ester as key steps. d-Mannitol has been utilized as the chiral pool material for the construction of the olefinic aldehyde and the Jacobsen hydrolytic kinetic resolution has been employed for the construction of the olefinic phosphonate ester.

Palladium(II)-catalyzed cyclization of urethanes and its application to a total synthesis of 1-deoxynojirimycin

We have employed a palladium(II)-catalyzed cyclization of allylic alcohol as a key reaction to achieve a total synthesis of the azasugar 1-deoxynojirimycin from o-mannitol. This reaction should be useful for the stereoselective construction of natural poly-substituted piperidine derivatives.

Total synthesis of (-)-microcarpalide from d-mannitol

The total synthesis of the actin-targeting metabolite (-)-microcarpalide is described. Ring-closing metathesis of a dienic ester was used as the key step. d-Mannitol was used as the chiral pool material for the construction of the olefinic acid moiety as well as the olefinic alcohol moiety of the molecule.

Palladium(II)-catalyzed cyclization of urethanes and total synthesis of 1-deoxymannojirimycin.

The palladium(II)-catalyzed cyclization of the urethane 8, which was derived from D-mannitol, gave the cyclic compound 9 with excellent diastereoselectivity. During these transformations, the Pd(II) species are not reduced and thus the catalyst can recycle without its reoxidation. The cycloadduct 9 was converted to 1-deoxymannojirimycin.