100991-92-2

Usage

Uses

Used in Pharmaceutical Industry:
1,4-Dideoxy-1,4-imino-D-arabinitol hydrochloride is used as an α-glucosidase (GAA) inhibitor for managing conditions related to glucose metabolism. Its inhibitory action on glycogen phosphorylase makes it a potential candidate for the treatment of diseases characterized by abnormal glucose metabolism, such as diabetes.
Used in Research Applications:
In the field of medical and biochemical research, DAB is utilized as a tool to study the role of glycogen phosphorylase in glycogenolysis. By inhibiting this enzyme, researchers can gain insights into the regulation of glucose production and its impact on various physiological processes.
Used in Drug Development:
The inhibitory properties of DAB make it a valuable compound in the development of new drugs targeting glycogenolysis-related conditions. Its potential application in the treatment of diabetes and other glucose metabolism disorders highlights its importance in the pharmaceutical sector.

Biochem/physiol Actions

Inhibitor of glycogen phosphorylase and α-glucosidases.

Upstream product

• 114395-15-2 5-Azido-5-desoxy-D-xylulose 
• 113200-91-2 (2R,3R,4R)-N-benzyl-3,4-bis(benzyloxy)-2-hydroxymethylpyrrolidine 
• 135791-03-6 (2R,3R,4R)-3,4-Dibenzyloxy-2-(benzyloxymethyl)pyrrolidine 
• 113571-55-4 (3R,4R,5R)-1-benzyl-3,4-bis(benzyloxy)-5-methoxymethoxymethyl-2-pyrrolidinone 
• 113200-90-1 (3S,4R,5R)-1-benzyl-3,4-bis(benzyloxy)-5-methoxymethoxymethyl-2-pyrrolidinone 
• 113571-53-2 (S)-1-benzyl-5-methoxymethoxymethyl-2-oxo-3-pyrroline 
• 154815-43-7 (S)-1-benzyl-5-methoxymethoxymethyl-2-pyrrolidinone 
• 94615-12-0 (S)-5-(methoxymethoxy)methyl-2-pyrrolidinone 
• 909801-43-0 2,3,5-tri-O-benzyl-1,4-benzylimino-1,4-dideoxy-D-arabinitol 
• 100937-52-8 1,4-dideoxy-1,4-imino-D-arabitol 
• 154815-46-0 (3R,4S,5S)-1-Benzyl-3,4,5-trihydroxy-5-methoxymethoxymethyl-pyrrolidin-2-one 
• 127298-78-6 (3R,4R,5R)-1-benzyl-4-benzyloxy-3-hydroxy-5-(methoxymethoxy)methyl-2-pyrrolidinone 
• 1427467-83-1 (2R,3R,4R)-4-azido-3,5-bis(benzyloxy)pentane-1,2-diol 
• 80817-67-0 methyl 1,3-O-isopropylidene-α-D-fructofuranoside 

Downstream Products

• 100937-52-8 1,4-dideoxy-1,4-imino-D-arabitol 

Relevant academic research and scientific papers

Regiospecific formation of sugar-derived ketonitrone towards unconventional: C -branched pyrrolizidines and indolizidines

The synthesis of unprecedented branched pyrrolizidines and indolizidines was accomplished via nitrone chemistry. The required ketonitrone, a known intermediate usually obtained as a mixture of regioisomers, was prepared in a pure form from d-arabinose by

A practical approach to Dideoxy-1,4- and 1,5-iminopentitols from protected sugar hemiacetals

The convenient and straightforward preparation of dideoxy-1,4- and 1,5-iminopentitol derivatives from protected sugar hemiacetals by way of N-tert-butanesulfinyl glycosylamines and open-chain aminoalditols is reported. The synthetic procedure is a method of choice for the making of these important scaffolds of biological interest.

A concise enantioselective synthesis of 1,4-dideoxy-1,4-imino-D-arabinitol using Co(III)(salen)-catalyzed hydrolytic kinetic resolution of a two-stereocentered anti-azido epoxide

A concise enantioselective synthesis of 1,4-dideoxy-1,4-imino-D-arabinitol, (+)-DAB-1, has been described in good overall yield (18.1%) and with high enantiomeric purity (up to 98% ee) starting from a simple raw material, cis-2-butene-1,4-diol. The Co-catalyzed hydrolytic kinetic resolution of a two-stereocentered racemic azido epoxide followed by asymmetric dihydroxylation of the alkene and ‘one pot’ reductive cyclisation of the azido diol are key reactions in the synthetic sequence.

Synthesis and Evaluation of Hybrid Structures Composed of Two Glucosylceramide Synthase Inhibitors

Glucosylceramide metabolism and the enzymes involved have attracted significant interest in medicinal chemistry, because aberrations in the levels of glycolipids that are derived from glucosylceramide are causative in a range of human diseases including lysosomal storage disorders, type2 diabetes, and neurodegenerative diseases. Selective modulation of one of the glycoprocessing enzymes involved in glucosylceramide metabolism - glucosylceramide synthase (GCS), acid glucosylceramidase (GBA1), or neutral glucosylceramidase (GBA2) - is therefore an attractive research objective. In this study we took two established GCS inhibitors, one based on deoxynojirimycin and the other a ceramide analogue, and merged characteristic features to obtain hybrid compounds. The resulting 39-compound library does not contain new GCS inhibitors; however, a potent (200nm) GBA1 inhibitor was identified that has little activity toward GBA2 and might therefore serve as a lead for further biomedical development as a selective GBA1 modulator. Taking the best of both: Two established glucosylceramide synthase (GCS) inhibitors were merged via convergent synthesis to obtain hybrid compounds. Members of this 39-compound library have characteristics of both parent GCS inhibitors. No new GCS inhibitors were established, but a potent (200nm) acid glucosylceramidase (GBA1) inhibitor was identified. This adamantanemethyloxypenanoic acid pyrrolidene-substituted derivative of eliglustat can serve as a lead for further biomedical development of selective GBA1 modulators.

A versatile approach to N-alkylated 1,4-dideoxy-1,4-imino-d-arabinitols and 1,4-dideoxy-1,4-imino-l-xylitols

A versatile and concise synthesis of N-alkylated 1,4-dideoxy-1,4-imino-d- arabinitol and 1,4-dideoxy-1,4-imino-l-xylitol derivatives is described. These were prepared using pseudohemiketal lactams as key intermediates, which in turn were obtained from suc

Synthesis of naturally occurring iminosugars from d-fructose by the use of a zinc-mediated fragmentation reaction

A short synthesis of 1,4-dideoxy-1,4-imino-d-arabinitol (DAB) and a formal synthesis of australine are described. In both cases, d-fructose is employed as the starting material and converted into a protected methyl 6-deoxy-6-iodo- furanoside. Zinc-mediate

Regioselective and diastereoselective amination of polybenzyl ethers using chlorosulfonyl isocyanate: Total syntheses of 1,4-dideoxy-1,4-imino-D-arabinitol and (-)-lentiginosine

The total syntheses of DAB1 (1) and (-)-lentiginosine (2) were concisely accomplished from D-lyxose via regioselective and diastereoselective NHCbz introduction using CSI, chemoselective removal of the Cbz protection, and ring-closing metathesis as key steps.

NEW SALT OF (2R,3R,4R)-3,4-DIHYDROXY-2-HYDROXYMETHYLPYRROLIDINE

This invention relates to (2R,3R,4R)-3,4-dihydroxy-2-hydroxymethylpyrrolidine, 2-naphthalenesulfonate, preparation thereof and use as therapeutic agent.

Salt of (2R,3R,4R)-3,4-dihydroxy-2-hydroxymethylpyrrolidine

A new salt of (2R,3R,4R)-3,4-dihydroxy-2-hyroxymethylpyrrolidine is disclosed. Specifically, (2R,3R,4R-3,4-dihydroxy-2-hydroxymethylpyrrolidine, 2-naphthalenesulfonate is disclosed, as well as its preparation and use for treating and preventing diabetes a

Stereoselective synthesis of (+)-1,8-Di-epi- and (-)-1-epi-swainsonine from an (S)-pyroglutamic acid derivative

(+)-1,8-Di-epi-swainsonine (15) and (-)-1-epi-swainsonine (17) were synthesized stereoselectively from an (S)-pyroglutamic acid derivative (1a). A (2R,3R,4R)-3,4-dihydroxy-2-hydroxymethylpyrrolidine derivative (6a) was prepared by cis-dihydroxylation of a