15218-38-9

Basic information

• Product Name: Nojirimycin
• Synonyms: Nojirimycin;5-O-Aza-D-glucopyranose;6β-(Hydroxymethyl)piperidine-2,3α,4β,5α-tetrol;Nojirimycin A;R-468;U-51640
• CAS NO: 15218-38-9
• Molecular Formula: C₆H₁₃NO₅
• Molecular Weight: 179.171
• Mol File: 15218-38-9.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 394.3°Cat760mmHg
• Flash Point: 214.3°C
• Appearance: /
• Density: 1.643g/cm³
• Vapor Pressure: 7.48E-08mmHg at 25°C
• Refractive Index: 1.634
• CAS DataBase Reference: Nojirimycin(CAS DataBase Reference)
• NIST Chemistry Reference: Nojirimycin(15218-38-9)
• EPA Substance Registry System: Nojirimycin(15218-38-9)

Safety Data

• Hazardous Substances Data: 15218-38-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H13NO5/c8-1-2-3(9)4(10)5(11)6(12)7-2/h2-12H,1H2/t2-,3-,4+,5-,6?/m1/s1

Upstream product

• 19130-95-1 5-amino-5-deoxy-D-glucose hydrogen sulfite 
• 114417-84-4 1-Desoxynojirimycin-1-sulfonsaeure 
• 14685-99-5 5-amino-5-deoxy-1,2-O-isopropylidene-α-D-glucofuranoside 
• 78698-43-8 5-amino-5-deoxy-L-altropyranose hydrogensulfite adduct 
• 108818-08-2 (2S,3S,4R,5R)-1-<(tert-butyldimethylsilyl)oxy>-2,3-(isopropylidenedioxy)-5-<<carbonyl>amino>-4,6-bis(methoxymethoxy)hexane 
• 108818-10-6 (2R,3S,4R,5R)-2,3-(isopropylidenedioxy)-5-<<carbonyl>amino>-4,6-bis(methoxymethoxy)hexanal 
• 108818-09-3 (2S,3S,4R,5R)-2,3-(isopropylidenedioxy)-5-<<carbonyl>amino>-4,6-bis(methoxymethoxy)hexan-1-ol 
• 108818-03-7 (2S,3S,4R,5R)-5-azido-1-<(tert-butyldimethylsilyl)oxy>-2,3-(isopropylenedioxy)-4,6-bis(methoxymethoxy)hexane 
• 108818-02-6 (2R,3R,4S,5S)-2-azido-6-<(tert-butyldimethylsilyl)oxy>-4,5-(isopropylidenedioxy)hexane-1,3-diol 
• 108818-07-1 (2S,3S,4R,5R)-5-amino-1-<(tert-butyldimethylsilyl)oxy>-2,3-(isopropylenedioxy)-4,6-bis(methoxymethoxy)hexane 
• 108817-99-8 (E)-3-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acrylic acid methyl ester 
• 108818-01-5 (2S,3R,4S,5S)-6-<(tert-butyldimethylsilyl)oxy>-2,3-epoxy-4,5-(isopropylidenedioxy)hexan-1-ol 
• 108818-00-4 (E)-(4S,5S)-6-<(tert-Butyldimethylsilyl)oxy>-4,5-O-(1-methylethylidene)-2-hexen-1-ol 
• 81703-56-2 5-amino-5-deoxy-D-glucose-1-sulfonic acid 

Downstream Products

• 14904-83-7 nojirimycin-δ-lactam 
• 19130-96-2 1,5-dideoxy-1,5-imino-D-glucitol 

Relevant articles and documents

Synthesis of Nojirimycin, d-glucopiperidinose.

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Stereoselective Homologation-Amination of Aldehydes by Addition of Their Nitrones to C-2 Metalated Thiazoles - A General Entry to α-Amino Aldehydes and Amino Sugars

A general method for the homologation of aldehydes to α-amino aldehydes (aminohomologation) has been developed, which employs nitrones as iminium derivatives of the aldehydes.Key operations include a) the addition of a thiazole metalated at C-2 to the N-benzylnitrone derived from the aldehyde, b) the reductive dehydroxylation of the resultant thiazolyl N-benzylhydroxylamine, and c) the unmasking of the formyl group from the thiazole ring.The homologation sequence was studied by employing nitrones derived from various chiral polyalkoxy aldehydes and dialdoses.The addition of 2-lithiothiazole to these nitrones was syn-selective, whereas the reaction with the same nitrones precomplexed with Lewis acids was anti-selective.Hence, from each nitrone a pair of diastereoisomeric hydroxylamines was obtained.These compounds were then converted by the above sequence into α-epimeric α-amino aldehydes.Model elaborations of some of these products afforded the amino sugars D-glucosamine, D-mannosamine, D-nojirimycin, and advanced intermediates for the synthesis of destomic acid and lincosamine. - Keywords: amino aldehydes; aminohomologation; amino sugars; nitrones; thiazoles

Synthesis of (+)- and (-)-nojirimycin and their 1-deoxy derivatives from myo-inositol

The conversion of the naturally abundant cyclitol, myo-inositol (4), into (+)-nojirimycin (1a), its enantiomer (1b), and their 1-deoxy analogues (2a and 2b) is described. Biological assay of 2a, 2b, and the bisulfite adducts of 1a and 1b (3a and 3b) showed that the compounds having the unnatural L-gluco configuration (2b and 3b) possess moderate-to-high inhibitory activity against almond β-D-glucosidase and bovine liver β-D-galactosidase.