14233-48-8

Basic information

• Product Name: 1,3,4,5-Tetra-O-benzyl-D-glucitol
• Synonyms: 2,3,4,6-Tetrakis-O-(phenylMethyl)-D-glucitol;2,3,4,6-Tetra-O-benzyl-D-glucitol
• CAS NO: 14233-48-8
• Molecular Formula: C₃₄H₃₈O₆
• Molecular Weight: 542.66
• Product Categories: Carbohydrates & Derivatives
• Mol File: 14233-48-8.mol
• Article Data: 29

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,3,4,5-Tetra-O-benzyl-D-glucitol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,4,5-Tetra-O-benzyl-D-glucitol(14233-48-8)
• EPA Substance Registry System: 1,3,4,5-Tetra-O-benzyl-D-glucitol(14233-48-8)

Safety Data

• Hazardous Substances Data: 14233-48-8(Hazardous Substances Data)

Usage

Description

1,3,4,5-Tetra-O-benzyl-D-glucitol, with the CAS number 14233-48-8, is a compound that is primarily utilized in the field of organic synthesis. It is a colorless liquid, which makes it suitable for various chemical reactions and processes.

Uses

Used in Organic Synthesis:
1,3,4,5-Tetra-O-benzyl-D-glucitol is used as a synthetic building block for the creation of more complex organic molecules. Its application in organic synthesis is due to its unique structure, which allows for the formation of various derivatives and the development of novel compounds with potential applications in different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,3,4,5-Tetra-O-benzyl-D-glucitol is used as an intermediate in the synthesis of various drugs and drug candidates. Its versatility in organic synthesis enables the development of new therapeutic agents with improved efficacy and reduced side effects.
Used in Chemical Research:
1,3,4,5-Tetra-O-benzyl-D-glucitol is also used as a research tool in chemical laboratories. Its unique properties make it an ideal candidate for studying various chemical reactions and mechanisms, contributing to the advancement of chemical knowledge and the development of new synthetic methods.
Used in Material Science:
In the field of material science, 1,3,4,5-Tetra-O-benzyl-D-glucitol can be used as a component in the development of new materials with specific properties. Its incorporation into polymers or other materials can lead to the creation of materials with enhanced characteristics, such as improved mechanical strength, thermal stability, or biocompatibility.

Upstream product

• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 38768-81-9 2,3,4,6-Tetra-O-benzyl-α-D-glucose 
• 78184-86-8 1,3,4,5-tetra-O-benzyl-α-L-sorbopyranoside 
• 76670-94-5 2,3,4,6-tetra-O-benzyl-5-dehydro-5-oxo-D-gluconamide 
• 83238-56-6 3,4,6-tri-O-benzyl-1,2-O-<(S)-benzylidene>-α-D-glucopyranose 
• 83238-55-5 3,4,6-tri-O-benzyl-1,2-O-<(R)-benzylidene>-α-D-glucopyranose 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 470-15-5 α-L-sorbopyranose 
• 78136-15-9 methyl 1,3,4,5-tetra-O-benzyl-α-L-sorbopyranoside 
• 3765-95-5 methyl β-L-sorbopyranoside 
• 14233-52-4 1,3,4,5-O-tetrabenzyl-L-sorbose 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 100-39-0 benzyl bromide 

Downstream Products

• 14233-49-9 2,3,4,6-tetra-O-benzyl-1-O-trityl-D-glucitol 
• 77698-65-8 1,5-di-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucitol 
• 1045730-76-4 (3R,4R,5S)-1,3,4,5-Tetrakis-benzyloxy-6-trityloxy-hexan-2-ol 
• 77638-00-7 2,3,4,6-tetra-O-benzyl-1,5-di-O-mesyl-D-glucitol 
• 79875-96-0 (R)-2-(benzyloxy)-1-((2R,3R,4S)-3,4-bis(benzyloxy)tetrahydrofuran-2-yl)ethanol 
• 78890-68-3 1-deoxy-2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 79875-95-9 2,3,6-tri-O-benzyl-5-O-toluene-p-sulphonyl-1,4-anhydro-D-glucitol 
• 79875-98-2 2,3,4,6-tetra-O-benzyl-1-O-tolylsulphonyl-D-glucitol 
• 150492-31-2 2,3,4,6-tetra-O-benzyl-1,5-di-O-tosyl-D-glucitol 
• 214041-43-7 (2R,3R,4S)-2,3,4,6-tetrakis(benzyloxy)-5-oxohexanal 
• 616215-36-2 (3R,4R,5S)-1,3,4,5-tetrakis(benzyloxy)-6-(tert-butyldiphenylsilyloxy)hexan-2-ol 
• 216758-20-2 AMP-DNM 
• 929619-03-4 2,3,4-tri-O-benzyl-N-pent-4'-enoyl-1-deoxynojirimycin 
• 929619-02-3 6-O-acetyl-2,3,4-tri-O-benzyl-N-pent-4'-enoyl-1-deoxynojirimycin 

Relevant articles and documents

Tuning the activity of iminosugars: novel N-alkylated deoxynojirimycin derivatives as strong BuChE inhibitors

We have designed unprecedented cholinesterase inhibitors based on 1-deoxynojirimycin as potential anti-Alzheimer’s agents. Compounds are comprised of three key structural motifs: the iminosugar, for interaction with cholinesterase catalytic anionic site (

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.

A Fluorescence Polarization Activity-Based Protein Profiling Assay in the Discovery of Potent, Selective Inhibitors for Human Nonlysosomal Glucosylceramidase

Human nonlysosomal glucosylceramidase (GBA2) is one of several enzymes that controls levels of glycolipids and whose activity is linked to several human disease states. There is a major need to design or discover selective GBA2 inhibitors both as chemical tools and as potential therapeutic agents. Here, we describe the development of a fluorescence polarization activity-based protein profiling (FluoPol-ABPP) assay for the rapid identification, from a 350+ library of iminosugars, of GBA2 inhibitors. A focused library is generated based on leads from the FluoPol-ABPP screen and assessed on GBA2 selectivity offset against the other glucosylceramide metabolizing enzymes, glucosylceramide synthase (GCS), lysosomal glucosylceramidase (GBA), and the cytosolic retaining β-glucosidase, GBA3. Our work, yielding potent and selective GBA2 inhibitors, also provides a roadmap for the development of high-throughput assays for identifying retaining glycosidase inhibitors by FluoPol-ABPP on cell extracts containing recombinant, overexpressed glycosidase as the easily accessible enzyme source.