115649-93-9

Basic information

• Product Name: 1-deoxycastanospermine
• Synonyms: 1-deoxycastanospermine
• CAS NO: 115649-93-9
• Molecular Formula: C8H15NO3
• Molecular Weight: 173.2096
• Mol File: 115649-93-9.mol

Chemical Properties

• Boiling Point: 353.3°Cat760mmHg
• Flash Point: 209.7°C
• Appearance: /
• Density: 1.38g/cm³
• Vapor Pressure: 2.1E-06mmHg at 25°C
• Refractive Index: 1.608
• CAS DataBase Reference: 1-deoxycastanospermine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-deoxycastanospermine(115649-93-9)
• EPA Substance Registry System: 1-deoxycastanospermine(115649-93-9)

Safety Data

• Hazardous Substances Data: 115649-93-9(Hazardous Substances Data)

Usage

Chemical Class

1-deoxycastanospermine belongs to the class of indolizidine alkaloids.

Natural Occurrence

It is found naturally in the seeds of the castor bean plant.

Pharmaceutical Applications

It has been studied for its potential pharmaceutical applications.

Enzyme Inhibition

It has inhibitory effects on certain enzymes, including alpha-glucosidases and lysosomal alpha-galactosidase.

Role in Carbohydrate Metabolism

The inhibited enzymes are involved in carbohydrate metabolism.

Therapeutic Potential

1-deoxycastanospermine has shown promising potential as a therapeutic agent for conditions such as diabetes and lysosomal storage disorders.

Value in Research and Drug Development

Its ability to modulate enzyme activity makes it a valuable chemical for research and drug development.

InChI:InChI=1/C8H15NO3/c10-6-4-9-3-1-2-5(9)7(11)8(6)12/h5-8,10-12H,1-4H2/t5-,6+,7-,8-/m1/s1

Upstream product

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• 196094-18-5 (3S,4R,5R)-3,4-Bis-benzyloxy-5-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-pyrrolidin-2-one 
• 115438-59-0 5,6,7,8-tetradeoxy-5,8-(N-benzyloxycarbonylimino)-1,2-O-isopropylidene-α-D-gluco-oct-1,4-furanose 
• 115438-60-3 (3aR,5R,6S,6aR)-2,2-Dimethyl-5-(R)-pyrrolidin-2-yl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol 
• 115438-57-8 5,8-benzyloxycarbonylimino-5,6,7,8-tetradeoxy-D-gluco-octose 
• 198493-30-0 tert-butyl (2S)-2-(2-oxoethyl)pyrrolidine-1-carboxylate 
• 1379528-14-9 (S,Z)-tert-butyl 2-(2-(tert-butyldimethylsilyloxy)vinyl)pyrrolidine-1-carboxylate 
• 1379528-16-1 (6S,7S,8R,8aR)-5-oxooctahydroindolizine-6,7,8-triyl triacetate 
• 1379528-15-0 (6S,7S,8R,8aR)-6,7,8-trihydroxyhexahydroindolizin-5(1H)-one 
• 1379528-08-1 (3S,4S,E)-3,4-bis(tert-butyldimethylsilyloxy)-3,4,8,9-tetrahydro-1H-azonin-2(7H)-one 
• 1379528-10-5 (S,Z)-2-(tert-butyldimethylsilyloxy)-1-(2-(2-(tertbutyldimethylsilyloxy)vinyl)pyrrolidin-1-yl)ethanone 
• 130359-90-9 Methanesulfonic acid 3-((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-yl)-propyl ester 
• 130359-41-0 2-((1R,2S,3R)-1,2,3,4-Tetrahydroxy-butyl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 130359-33-0 ethyl 3-(1,2;3,4-di-O-isopropylidene-β-D-arabinopyranosyl)propanoate 

Relevant articles and documents

Contribution to the synthesis of polyhydroxylated indolizidines starting from sugar isothiocyanates

A straightforward stereoselective route towards castanospermine analogues starting from the corresponding d-gluco- and l-ido-hexofuranose isothiocyanates (5S)-2 and (5R)-2 is described. The key transformations of this approach rely on ring-closing metathe

Divergent total synthesis of 1,6,8a-tri-epi-castanospermine and 1-deoxy-6,8a-di-epi-castanospermine from substituted azetidin-2-one (β-lactam), involving a cascade sequence of reactions as a key step

A divergent, short, and novel total synthesis of 1,6,8a-tri-epi- castanospermine (7) and 1-deoxy-6,8a-di-epi-castanospermine (8) has been developed via a common precursor, 15, obtained from d-mannitol derived β-lactam. The key step involves a one pot cascade sequence of trimethyl sulfoxonium ylide based cyclization of epoxy sulfonamide 14via epoxide ring opening, one carbon homologation followed by intramolecular cyclization. This journal is the Partner Organisations 2014.

Asymmetric syntheses of 1-deoxy-6,8a-di-epi-castanospermine and 1-deoxy-6-epi-castanospermine

Asymmetric syntheses of both 1-deoxy-6,8a-di-epi-castanospermine and 1-deoxy-6-epi-castanospermine, polyhydroxylated indolizidine alkaloids that act as selective glycosidase inhibitors, have been accomplished in seven steps. The key feature of our unique syntheses includes the stereoselective introduction of the C-3 and C-4 hydroxyl groups utilizing the aza-Claisen rearrangement-induced ring expansion of 1-acyl-2-alkoxyvinyl pyrrolidine and a substrate-controlled stereoselective transannulation of the resulting azoninone intermediate.

A new synthetic access to bicyclic polyhydroxylated alkaloid analogues from pyranosides

A facile, versatile and stereoselective synthesis of bicyclic polyhydroxylated alkaloids as castanospermine analogues is described. The synthetic route started from methyl pyranosides. The key steps involved a high-yielding expeditious one-pot tandem reaction from alkenes to N-substituted δ-lactams. The δ-lactams were stereoselectively vinylated to give the dienes, which were followed by the ring-closing metathesis to produce the cyclized products. The functional group transformations of the resulting bicyclic compounds furnished diverse polyhydroxylated alkaloids in good yields. The Royal Society of Chemistry 2010.

A short and common stereoselective approach to 5/6, 6/6, 6/7 bicyclic aza sugars

An efficient and highly stereoselective approach to bicyclic aza sugars is described using Grignard reaction on an N-benzyl imine derived from 3-O-benzyl-1,2-O-isopropylidine-α-d-xylo-pentodialdofuranose, ring closing metathesis, and reductive cyclization

The 5-endo-trig cyclization of D-glucose derived γ-alkenylamines with mercury (II) salts: Synthesis of 1-deoxy-castanospermine and its 8a-epi-analogue

The intramolecular aminomercuration of γ-alkenylamines 1a, 1b and 4 was shown to afford the 5-endo-trig cyclized product exclusively in good yield. The utility of pyrrolidine derivatives thus obtained from D-glucose derived γ-alkenylamines 1a and 1b was d

A convenient synthesis of 1-deoxy-8a-epi-castanospermine diastereoisomers (6R,7R,8S,8aS)-6,7,8-trihydroxyindolizidine and (6R,7R,8R,8aS)-6,7,8trihydroxyindolizidine

An efficient synthesis of (6R,7R,8S,8aS)-6,7,8-trihydroxyindolizidine and (6R,7R,8R,8aS)-6,7,8-trihydroxyindolizidine is described from readily available N-BOC-L-proline, (BOC = tert-butoxycarbonyl) which involves the addition of ethyl lithiopropiolate to the aldehyde derived from N-BOC-L-proline as a key step, then cyclization to construct indolizidine skeletons and asymmetric dihydroxylation. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Intermolecular Michael addition of substituted amines to a sugar-derived α,β-unsaturated ester: Synthesis of 1-deoxy-D-gluco- and -L-ido-homonojirimycin, 1-deoxy-castanospermine and 1-deoxy-8a-epi-castanospermine

The synthesis of polyhydroxylated piperidine alkaloids, namely, 1-deoxy-D-gluco-homonojirimycin 3a, 1-deoxy-L-ido-homonojirimycin 3b, and indolizidine alkaloids 1-deoxy-castanospermine 5a and 1-deoxy-8a-epi-castanospermine 5b, has been achieved. The key step involved is the intermolecular Michael addition of benzylamine to α,β-unsaturated ester 1, derived from D-glucose, which afforded diastereomeric mixture of β-amino esters 6a and 6b with D-gluco- and L-ido- configuration at C5, respectively. Attempts were made to increase and/or alter the diastereoselectivity at the newly generated stereocenter. The high stereoselectivity, in favor of L-ido-isomer 6b, was achieved under kinetically controlled conditions by using lithium N-benzyl amide as a Michael donor. The β-amino esters 6a and 6b represent common intermediates to target molecules. Thus, LAH reduction of 6a and 6b, individually, gave β-amino alcohol 7a and 7b. Sequential hydrogenolysis, selective protection of the amino group, followed by hydrolysis of the 1,2-acetonide functionality, and hydrogenation gave 3a and 3b, respectively. On the other hand, the β-amino ester 6a was converted to γ-amino ester 13a by Arndt-Eistert synthesis, which on hydrogenolysis and treatment with sodium acetate gave γ-lactam 14a. The LAH reduction afforded pyrrolidene. The N-protection-hydrolysis-hydrogenation cascade successfully executed, and 1-deoxy-castanospermine 5a was obtained in good yield. The same sequence of reactions was applied to β-amino ester 6b, which afforded 1-deoxy-8a-epi-castanospermine 5b.

A short and efficient synthesis of 1-deoxy-castanospermine and 1-deoxy-8a-epi-castanospermine

A new route for the synthesis of 1-deoxy-castanospermine 2 and 1-deoxy-8a-epi-castanospermine 3 has been developed via a sequential triple reductive amination process of a suitably protected D-gluco-oct-5-ulo-1,8-dialdose, which was easily prepared by three carbon homologation of readily available α-D-xyclo-pentodialdose using an appropriate Grignard reagent followed by oxidation.

Synthesis of 4-octuloses, V. - 4-Octulose derivatives as key intermediates in a new and short synthesis of polyhydroxyindolizidines

Reaction of 3 with (cyanomethylene)triphenylphosphorane in refluxing dichloromethane or methanol gave mixtures of 4a and 4b in ratios of about 3:1 and 1:3, respectively. The same reaction performed with the furanoid isomer 5 afforded 6a and 6b in (E)/(Z)