105990-40-7

Basic information

• Product Name: (2S,3S,4R)-2-(hydroxymethyl)pyrrolidine-3,4-diol
• Synonyms: 1,4-Dideoxy-1,4-imino-L-ribitol; 3,4-Pyrrolidinediol, 2-(hydroxymethyl)-, (2S,3S,4R)-
• CAS NO: 105990-40-7
• Molecular Formula: C₅H₁₁NO₃
• Molecular Weight: 133.1457
• Mol File: 105990-40-7.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 319.1°C at 760 mmHg
• Flash Point: 188.8°C
• Density: 1.368g/cm³
• Vapor Pressure: 2.84E-05mmHg at 25°C
• Refractive Index: 1.554
• CAS DataBase Reference: (2S,3S,4R)-2-(hydroxymethyl)pyrrolidine-3,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,4R)-2-(hydroxymethyl)pyrrolidine-3,4-diol(105990-40-7)
• EPA Substance Registry System: (2S,3S,4R)-2-(hydroxymethyl)pyrrolidine-3,4-diol(105990-40-7)

Safety Data

• Hazardous Substances Data: 105990-40-7(Hazardous Substances Data)

Usage

General Description

"(2S,3S,4R)-2-(hydroxymethyl)pyrrolidine-3,4-diol" is a chemical compound with the molecular formula C5H11NO3. It is a derivative of pyrrolidine, a heterocyclic organic compound commonly found in natural products and pharmaceuticals. (2S,3S,4R)-2-(hydroxymethyl)pyrrolidine-3,4-diol contains a hydroxymethyl group and two hydroxyl groups attached to the pyrrolidine ring. It is a chiral molecule, meaning it has non-superimposable mirror images, and the (2S,3S,4R) configuration indicates the stereochemistry of its atoms. (2S,3S,4R)-2-(hydroxymethyl)pyrrolidine-3,4-diol has potential applications in the fields of medicinal chemistry, drug development, and organic synthesis due to its unique structural features and potential biological activities.

Upstream product

• 101242-41-5 methyl 2,3-di-O-benzoyl-4-O-trifluoromethylsulfonyl-α-L-arabinopyranoside 
• 1579996-64-7 ((2S,3S,4R)-1-benzyl-3,4-bis(benzyloxy)pyrrolidin-2-yl)methanol 
• 105888-78-6 (3aS,4R,6aR)-4-Formyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylic acid benzyl ester 
• 186025-85-4 (2S,3S)-2,3-Dihydroxy-3-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-propionic acid methyl ester 
• 186025-75-2 (R)-(-)-methyl (Z)-3-(4,5-dihydro-2-phenyl-4-oxazolyl)-2-propenoate 
• 570385-37-4 (3aS,4S,6aR)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-5-(2-nitro-benzenesulfonyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole 
• 570385-40-9 (S)-1-[(3aS,4S,6aR)-2,2-Dimethyl-5-(2-nitro-benzenesulfonyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-ethane-1,2-diol 
• 570385-42-1 (3aS,4R,6aR)-2,2-Dimethyl-5-(2-nitro-benzenesulfonyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbaldehyde 
• 7306-64-1 2,3,5,6-di-O-isopropylidene-D-mannono-1,4-lactone 
• 649745-80-2 (S)-4-((4S,5R)-2,2-Dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 160797-20-6 (4S)-[(1S,2R)-dihydroxybut-3-enyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 
• 115889-54-8 (2S,3S,4S)-4-Amino-2,3,5-trihydroxy-pentanal 
• 117770-00-0 (2S,3S,4R)-2-hydroxymethyl-3,4-O-isopropylidenepyrrolidine-3,4-diol 
• 186025-87-6 Benzoic acid (2S,3S,4S)-3,4-dihydroxy-5-oxo-pyrrolidin-2-ylmethyl ester 

Downstream Products

• 117894-12-9 (2S,3S,4S)-3,4-dihydroxy-2-hydroxymethyl-1-methylpyrrolidine 
• 1333523-99-1 (2S,3S,4S)-3,4-diacetoxy-2-[(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyloxy)methyl]pyrrolidine 
• 1333523-84-4 (2S,3S,4S)-3,4-dihydroxy-1-(tert-butoxycarbonyl)-2-[(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyloxy)methyl]pyrrolidine 
• 1333524-01-8 (2S,3S,4S)-3,4-diacetoxy-2-[(2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-L-arabinofuranosyloxy)methyl]pyrrolidine 
• 1333523-86-6 (2S,3S,4S)-3,4-dihydroxy-1-(tert-butoxycarbonyl)-2-([2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->5)-2,3-di-O-benzoyl-α-L-arabinofuranosyloxy]methyl)pyrrolidine 
• 100991-91-1 1,4-dideoxy-1,4-imino-L-arabinitol hydrochloride 

Relevant articles and documents

Indium-mediated coupling of 3-bromopropenyl acetate with (S)-Garner aldehyde: a route to 1,4-dideoxy-1,4-L-iminoribitol

The indium organometallic complex generated by metallic indium and 3-bromopropenyl acetate in THF adds to the Garner aldehyde in excellent yield and with high diastereoselectivity; the usefulness of the corresponding anti-anti adduct was demonstrated by developing a short synthesis of the title compound, an azasugar known as a glycosidase inhibitor.

METHODS OF TREATING POMPE DISEASE

Disclosed herein are novel uses of ADMDP stereoisomers or their derivatives for the manufacture of a medicament for treating Pompe disease. Accordingly, the present disclosure provides a method of treating Pompe disease in a subject. The method includes the step of, administering to the subject a therapeutically effective amount of a compound of formula (I), or a salt, an ester or a solvate thereof, wherein R1 and R2 are independently H or alkyl optionally substituted by -NH2 or -OH, so as to ameliorate, alleviate mitigate and/or prevent symptoms associated with the Pompe disease. According to certain embodiments of the present disclosure, the compound of formula (I) may serve a stabilizer of α-glucosidase via preventing its denaturalization of deactivation.

Synthesis of pyrrolidine iminosugars, (-)-lentiginosine, (-)-swainsonine and their 8a-epimers from d-glycals

Synthesis of pyrrolidine iminosugars has been described from d-glycals via dihydroxylation, oxidative cleavage and double nucleophilic displacement as the key steps. The pyrrolidines obtained have been utilized for the synthesis of important bicyclic iminosugars, viz. (-)-lentiginosine and (-)-swainsonine and their 8a-epimers, which are known to be glycosidase inhibitors.

Redesign of the phosphate binding site of L -rhamnulose- 1-phosphate aldolase towards a dihydroxyacetone dependent aldolase

The aldol addition of unphosphorylated dihydroxyacetone (DHA) to aldehydes catalyzed by L-rhamnulose-1-phosphate aldolase (RhuA), a dihydroxyacetone phosphate-dependent aldolase, is reported. Moreover, a single point mutation in the phosphate binding site