114976-76-0

Basic information

• Product Name: 1,4-DIDEOXY-1,4-IMINO-D-MANNITOL HYDROCHLORIDE
• Synonyms: DMJ;1,4-DIDEOXY-1,4-IMINO-D-MANNITOL HCL;1,4-DIDEOXY-1,4-IMINO-D-MANNITOL HYDROCHLORIDE;1,'-dideoxy-1,4-imino-D-mannitol*hydorchloride;3,4-Pyrrolidinediol, 2-(1S)-1,2-dihydroxyethyl-, hydrochloride, (2R,3S,4R)-;1,4-DIDEOXY-1,4-IMINO-D-MANNITOL HYDORCHLORIDE;1,4-Dideoxy-1,4-imino-D-mannitol hydrochloride ,98%;(2R,3S,4R)-2-[(1S)-1,2-Dihydroxyethyl]-3,4-pyrrolidinediol Hydrochloride
• CAS NO: 114976-76-0
• Molecular Formula: C₆H₁₃NO₄*ClH
• Molecular Weight: 199.63
• Product Categories: All Inhibitors;Inhibitors;InhibitorsEnzyme Inhibitors by Enzyme;Glycobiology;Inhibitors and Substrates;L to;Mannosidase, alpha-
• Mol File: 114976-76-0.mol

Chemical Properties

• Melting Point: 147-148°C
• Boiling Point: 448.6°Cat760mmHg
• Flash Point: 258°C
• Appearance: /
• Density: 1.492g/cm³
• Storage Temp.: 2-8°C
• Solubility: Water
• Stability: Hygroscopic
• CAS DataBase Reference: 1,4-DIDEOXY-1,4-IMINO-D-MANNITOL HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-DIDEOXY-1,4-IMINO-D-MANNITOL HYDROCHLORIDE(114976-76-0)
• EPA Substance Registry System: 1,4-DIDEOXY-1,4-IMINO-D-MANNITOL HYDROCHLORIDE(114976-76-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 114976-76-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,4-Dideoxy-1,4-imino-D-mannitol hydrochloride is used as a competitive glycosidase inhibitor for its ability to inhibit jack bean and, to a lesser extent, lysosomal alpha-mannosidase. This makes it a valuable compound in the development of drugs targeting various diseases and conditions.
Used in Research and Development:
In the field of research and development, 1,4-dideoxy-1,4-imino-D-mannitol hydrochloride serves as an important tool for studying the structure and function of glycosidases and mannosidases. Its inhibitory properties allow scientists to gain insights into the mechanisms of these enzymes and their roles in biological processes.
Used in Drug Design and Synthesis:
Due to its structural similarity to swainsonine, 1,4-dideoxy-1,4-imino-D-mannitol hydrochloride can be utilized in the design and synthesis of new drugs targeting specific enzymes or pathways. Its unique properties make it a promising candidate for the development of novel therapeutic agents.

Upstream product

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Relevant articles and documents

Synthesis and glycosidase inhibition of: N-substituted derivatives of 1,4-dideoxy-1,4-imino-d-mannitol (DIM)

N-Substituted derivatives of 1,4-dideoxy-1,4-imino-d-mannitol (DIM), the pyrrolidine core of swainsonine, have been synthesized efficiently and stereoselectively from d-mannose with 2,3:5,6-di-O-isopropylidene DIM (10) as a key intermediate. These N-substituted derivatives include N-alkylated, N-alkenylated, N-hydroxyalkylated and N-aralkylated DIMs with the carbon number of the alkyl chain ranging from one to nine. The obtained 33 N-substituted DIM derivatives were assayed against various glycosidases, which allowed a systematic evaluation of their glycosidase inhibition profiles. Though N-substitution of DIM decreased their α-mannosidase inhibitory activities, some of the derivatives showed significant inhibition of other glycosidases.

Chemistry of epoxysulfones: A new route to polyhydroxylated pyrrolidines

A new methodology for the synthesis of polyhydroxylated pyrrolidines using epoxysulfones is described. The synthesis of two natural glycosidase inhibitors, 1,4-dideoxy-1,4-imino-D-lyxitol and 1,4-dideoxy-1,4-imino-D-mannitol (DIM), is reported.

Efficient stereodivergent synthesis of 1,4-dideoxy-1,4-iminohexitols from an (S)-glyceraldimine

A stereodivergent synthesis of 1,4-dideoxy-1,4-imino-D-mannitol I and D-allitol III from an (S)-glyceraldimine, which is easily prepared from D-mannitol, has been achieved with overall yields of 62% and 49%, respectively. The synthesis is based on the add

Synthesis of iminopolyols via Henry reaction: A short route to the α-mannosidase inhibitor 1,4-dideoxy-1,4-imino-D-mannitol and to amino analogues

The α-mannosidase inhibitor 1,4-dideoxy-1,4-imino-D-mannitol (DIM) as well as amino analogues of DIM and of deoxy-manno-nojirimycin, respectively, have been prepared using a diastereoselective nitroaldol addition as the key step.

Enantiospecific and stereoselective synthesis of polyhydroxylated pyrrolidines and indolizidines from trans-4-hydroxy-L-proline

We have developed a short, efficient, and stereoselective synthesis of polyhydroxylated pyrrolidine and indolizidine glycosidase inhibitors starting from 4-hydroxy-L-proline. The regio- and stereoselective hydroxylation of an N-Pf-4-oxoproline enolate and the stereoselective reduction of the resulting keto alcohol allowed us to introduce the cis diol present in the target compounds. The different side chains needed to complete the syntheses of the target compounds were introduced by reduction of the ester group of a substituted proline or by reaction of organolithium or organomagnesium reagents with the same group followed by stereoselective reduction of the resulting ketones. Hydrogenolysis of the alcohols thus obtained gave the hydrochlorides of the desired pyrrolidine glycosidase inhibitors, which were obtained in nine steps in overall yields greater than 50%. The indolizidine glycosidase inhibitor 8-epi-swainsonine was also prepared using this approach.