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
• Article Data: 15

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

General Description

The chemical compound "(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one" is a piperidine derivative with three benzyloxy groups and one benzyloxymethyl group attached to the piperidine ring. It has a molecular formula of C33H33NO5 and a molecular weight of 527.62 g/mol. (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one can be used as an intermediate or building block in organic synthesis and drug discovery due to the presence of multiple functional groups, which can be modified to create different derivatives with potential biological or pharmaceutical activities.

Upstream product

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

Downstream Products

• 121209-13-0 (3R,4S,5R,6R)-N-Benzyl-3,4,5-tris(benzyloxy)-6-<(benzyloxy)methyl>piperidin-2-one; Pentabenzyl-D-nojirilactam 
• 153996-70-4 2,3,4,6-tetra-O-benzyl-D-glucono-δ-thiolactam 
• 121209-12-9 2,3,4,6-tetra-O-benzyl-5-imino-5-deoxy-glucopyranose 
• 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 
• 272123-95-2 5-amino-3,4,6-tri-O-benzyl-5-deoxy-D-gluconolactam 
• 72599-27-0 N-butyldeoxynojirimycin 
• 174591-18-5 (3aR,3bS,4R,5S,6R,8aS)-4,5,6-Tris-benzyloxy-2,2-dioxo-hexahydro-1,3-dioxa-2λ⁶-thia-7a-aza-cyclopenta[a]inden-7-one 
• 174504-17-7 (E)-3-((2R,3R,4S,5R)-1-Allyl-3,4,5-tris-benzyloxy-6-oxo-piperidin-2-yl)-acrylic acid methyl ester 
• 174504-16-6 (2S,3R,4S,5R)-1-Allyl-3,4,5-tris-benzyloxy-6-oxo-piperidine-2-carbaldehyde 
• 174504-15-5 (3R,4S,5R,6R)-1-Allyl-3,4,5-tris-benzyloxy-6-hydroxymethyl-piperidin-2-one 
• 174504-18-8 (6R,7S,8R,8aR)-6,7,8-Tris-benzyloxy-6,7,8,8a-tetrahydro-3H-indolizin-5-one 

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.

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 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.