77174-08-4

Basic information

• Product Name: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one
• Synonyms: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one
• CAS NO: 77174-08-4
• Molecular Weight: 537.656
• Mol File: 77174-08-4.mol

Chemical Properties

• CAS DataBase Reference: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one(77174-08-4)
• EPA Substance Registry System: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one(77174-08-4)

Safety Data

• Hazardous Substances Data: 77174-08-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one serves as a versatile intermediate in organic synthesis, where its functional groups can be selectively modified to produce a variety of chemical derivatives. This adaptability makes it a promising candidate for the development of new compounds with tailored properties.
Used in Drug Discovery:
In the pharmaceutical industry, (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one is utilized as a building block for drug discovery. Its multiple functional groups allow for the creation of diverse molecular structures with potential biological activities. (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one can be further optimized to develop new drugs with improved efficacy and selectivity for various therapeutic targets.

Upstream product

• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 153996-70-4 2,3,4,6-tetra-O-benzyl-D-glucono-δ-thiolactam 
• 76670-94-5 2,3,4,6-tetra-O-benzyl-5-dehydro-5-oxo-D-gluconamide 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 76670-93-4 2,3,4,6-tetra-O-benzyl-D-gluconamide 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 153996-65-7 (2R,3S,4S,5R)-3,4,5-tris(benzyloxy)-2-<(benzyloxy)methyl>-6-ethoxy-2,3,4,5-tetrahydropyridine 
• 76670-95-6 (3R,4S,5S,6S)-6-Hydroxy-3,4,5-tris(benzyloxy)-6-<(benzyloxy)methyl>piperidin-2-one 
• 76738-51-7 (3R,4S,5S,6R)-6-Hydroxy-3,4,5-tris(benzyloxy)-6-<(benzyloxy)methyl>piperidin-2-one 
• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 

Downstream Products

• 153996-65-7 (2R,3S,4S,5R)-3,4,5-tris(benzyloxy)-2-<(benzyloxy)methyl>-6-ethoxy-2,3,4,5-tetrahydropyridine 
• 174504-14-4 (3R,4S,5R,6R)-1-Allyl-3,4,5-tris-benzyloxy-6-benzyloxymethyl-piperidin-2-one 
• 139189-64-3 (5R,6R,7S,8S)-6,7,8-tris(benzyloxy)-5-<(benzyloxy)methyl>-5,6,7,8-tetrahydro-tetrazolo<1,5-a>pyridine 
• 158349-24-7 (3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-<(benzyloxy)methyl>piperidin-2-one 
• 272123-95-2 5-amino-3,4,6-tri-O-benzyl-5-deoxy-D-gluconolactam 
• 1570183-94-6 (2S,3S,4R,5R,6R)-2-allyl-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidine 
• 950599-08-3 (2R,3S,4R,5R,6R)-2-allyl-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidine 
• 72599-27-0 N-butyldeoxynojirimycin 

Relevant articles and documents

Synthesis of 1-deoxynojirimycin: Exploration of optimised conditions for reductive amidation and separation of epimers

1-Deoxynojirimycin (DNJ), which has importance with respect to sugar processing enzymes, is a synthetic target for chemists. A key step in the synthesis of DNJ is the preparation of 2,3,4,6-tetra-O-benzyl-D-glucono-δ-lactam. By varying reaction parameters such as temperature, solvent and reducing reagent, improvements on previous methods are described. A novel approach for the synthesis of 2,3,4,6-tetra-O-benzyl-5-dehydro-5-deoxo-D-gluconamide has been developed by using PCC as an oxidising agent. Separation of epimers permitted DNJ to be obtained in 85% yield after reduction and hydrogenolysis steps.

Total synthesis of N-butyl-1-deoxynojirimycin

N-Butyl-1-deoxynojirimycin (NB-DNJ) derived from imino sugar deoxynojirimycin (DNJ) has been approved for the treatment of Gaucher’s disease. Herein, a facile and efficient synthetic procedure for NB-DNJ has been described. Comparing to the methods reported previously,methanesulfonyl group was used as a leaving group for easy displacement upon attack by the imine in the sugar ring, leading to a high yield during the introduction of the n-butyl group. Thismethod can serve as an excellent protocol for the synthesis of DNJ derivatives with a variety of N-alkyl substituents and for large-scale production.

Sugar-derived cyclic imines: One-pot synthesis and direct functionalization

A simple method for the synthesis of sugar-derived imines by a Schwartz's reagent reduction of easily available sugar lactams has been described. A direct addition of nucleophiles to the generated in situ cyclic imines and subsequent deprotection of hydroxyl function allows to convert sugar lactams in polyhydroxylated pyrrolidines and piperidines.

Synthesis of polyhydroxylated quinolizidine and indolizidine scaffolds from sugar-derived lactams via a one-pot reduction/Mannich/Michael sequence

A direct approach to the synthesis of indolizidine and quinolizidine scaffolds of iminosugars is described. The presented strategy is based on a one-pot sugar lactam reduction with Schwartz's reagent followed by a diastereoselective Mannich/Michael tandem reaction of the resulting sugar imine with Danishefsky's diene. The stereochemical course of the investigated reaction has been explained in detail. The obtained bicyclic products are attractive building blocks for the synthesis of various naturally occurring polyhydroxylated alkaloids and their derivatives.

Synthesis of glycosylamines and glyconamides using molecular iodine

We describe herein the synthesis of glyconamides and glycosylamines usingmolecular iodine on benzylated carbohydrates. During the improvement and the optimization of the direct oxidative amidation reaction,we also discovered the possibility to form glycosylamines with excellent yields and short reaction times in comparison with the previously reported procedures. Advantages of these methods are the operational simplicity, elimination of use of complicated reagents and procedures, and generality of the reactions. Our methodology is an excellent access to precursors of N-alkyliminosugars and imino-C-glycosides.

Structure-activity relationships in a series of C2-substituted gluco-configured tetrahydroimidazopyridines as β-glucosidase inhibitors

Inhibition of glycoside hydrolases has widespread application in treatment of diabetes, viral infections, lysosomal storage diseases and cancers. Gluco-configured tetrahydroimidazopyridines are the most potent β-glucosidase inhibitors reported to date. Using transition state mimic strategy, a series of C2-substituted gluco-configured tetrahydroimidazopyridines were designed and synthesized. Compounds 3 (Ki = 0.64 nM) and 5 (Ki = 0.58 nM) showed stronger inhibitory potency against β-glucosidase. Maestro 9.1 was used to study the structure-activity relationships by docking the compounds into the β-glucosidase active sites. Crown Copyright

Glycosidase inhibition with fullerene iminosugar balls: A dramatic multivalent effect

(Figure Presented) Superball ! A dodecavalent iminosugar derivative with a fullerene core (see picture) shows a binding enhancement of up to three orders of magnitude over the corresponding monovalent ligand in glycosidase inhibition assays. This is the first evidence of a significant multivalent effect in glycosidase inhibition.

Cyclization dichotomy of D-xylo-hex-5-ulosonamides and synthesis of piperidine analogs of aldohexoses and aldohexono-1,5-lactones

The preparation of 2,3,4,6-tetra-O-benzyl-S-D-xylo-hex-5-ulosonamides 3a and 3b and their cyclization to 5-amino-2,3,4,6-tetra-O-benzyl-5-deoxy-D-glucono-1,5-lactam (4) and 5-amino-2,3,4,6-tetra-O-benzyl-S-deoxy-D-talono-1,5-lactam (5) or to 2,3,4,6-tetra

An advantageous synthesis of 5,6,7,8-tetra-hydrotetrazolo[1,5- a]pyridines

The one-step synthesis of various O-benzyl-protected glyconotetrazoles from the corresponding glyconolactams is reported. The method is superior to the previously employed cycloaddition of azidonitriles as it uses readily available starting materials and leads to higher yields.

Structure-activity relations for imidazo-pyridine-type inhibitors of β-D-glucosidases

The triazole 7 and the known gluco- and manno-configurated imidazoles 10 and 11 have been prepared by annulation of the azole ring to the aldonothiolactam 14 in a Hg(OAc)2-promoted reaction with either hydrazinecarbaldehyde or aminoacetaldehyde dimethyl acetal. Depending upon the reaction conditions, the synthesis of the imidazoles yielded mostly the gluco-imidazole 19 or a mixture of the gluco/manno epimers 19/20. In contrast to the triazole 4, the isomeric triazole 7 proved a good inhibitor of retaining β-glucosidases from sweet almonds and from Caldocellum saccharolyticum. This observation and the qualitative correlation between basicity and inhibitory power of the tetrahydropyridoazoles provide further evidence for the hypothesis of the 'lateral protonation' of glycosides by (some) retaining β-glucosidases.