85624-09-5

Basic information

• Product Name: 1,2-ISOPROPYLIDENE SWAINSONINE
• Synonyms: 1,2-ISOPROPYLIDENE SWAINSONINE;1,2-O-ISOPROPYLIDENE 8A,B-OCTAHYDROINDOLIZIDINE-1A,2A,8B-TRIOL;1,2-O-Isopropylidene 8a,-Octahydroindolizidine-1a,2a,8-triol;(3aR,9R,9aR,9bS)-Octahydro-2,2-diMethyl-1,3-dioxolo[4,5-a]indolizin-9-ol;1,2-O-Isopropylidene 8α,β-Octahydroindolizidine-1α,2α,8β-triol;Swainsonine Acetonide
• CAS NO: 85624-09-5
• Molecular Formula: C₁₁H₁₉NO₃
• Molecular Weight: 213.27
• Product Categories: Glycosidase Inhibitors;Inhibitors
• Mol File: 85624-09-5.mol
• Article Data: 25

Chemical Properties

• Appearance: /
• Solubility: Chloroform
• CAS DataBase Reference: 1,2-ISOPROPYLIDENE SWAINSONINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-ISOPROPYLIDENE SWAINSONINE(85624-09-5)
• EPA Substance Registry System: 1,2-ISOPROPYLIDENE SWAINSONINE(85624-09-5)

Safety Data

• Hazardous Substances Data: 85624-09-5(Hazardous Substances Data)

Usage

Description

1,2-Isopropylidene Swainsonine is a white crystalline solid that serves as an intermediate in the synthesis of Swainsonine (S885000), a plant alkaloid derived from Swainsona canescens, a leguminous plant. It is a reversible, active-site directed inhibitor of α-mannosidase at concentrations of 5-10mM, and at acid pH, it resembles an intermediate in the hydrolysis of mannosidases.

Uses

Used in Pharmaceutical Industry:
1,2-Isopropylidene Swainsonine is used as a key intermediate in the synthesis of Swainsonine, which has potential applications in the development of drugs targeting glycobiology and lysosomal storage disorders. Its ability to inhibit α-mannosidase makes it a valuable compound for research and drug discovery in this field.
Used in Research Applications:
1,2-Isopropylidene Swainsonine is used as a research compound for studying the mechanisms of α-mannosidase inhibition and its effects on glycoprotein processing. This knowledge can contribute to the understanding of various diseases and the development of therapeutic strategies.
Used in Synthesis of Other Compounds:
1,2-Isopropylidene Swainsonine can also be used as a starting material or intermediate in the synthesis of other related compounds with potential biological activities or applications in various industries.

Upstream product

• 119011-32-4 (3aR,9bS)-2,2-Dimethyl-3a,4,6,7,8,9b-hexahydro-[1,3]dioxolo[4,5-a]indolizine 
• 91652-64-1 (1R,3S,4S,5S,6R)-7-aza-3-benzyloxy-4,5-isopropylidenedioxy-2-oxa-bicyclo<4,4,0>-decane 
• 130412-70-3 (-)-(7S,8R)-7,8-O-isopropylidenedioxy-2-oxo-1-azabicyclo<4.3.0>non-5-ene 
• 107080-62-6 (1S,2R,8R,8aR)-8-hydroxy-1,2-(isopropylidenedioxy)octahydroindolizin-5-one 
• 98361-98-9 (E)-3-((2R,3S)-3-{(4R,5R)-2,2-Dimethyl-5-[(2,2,2-trifluoro-acetylamino)-methyl]-[1,3]dioxolan-4-yl}-oxiranyl)-acrylic acid ethyl ester 
• 72741-87-8 swainsonine 
• 77-76-9 2,2-dimethoxy-propane 
• 154815-12-0 (3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-9-(phenylmethoxy)-1,3-dioxolo[4,5-a]indolizine 
• 154815-09-5 (2R,3R)-3-(benzyloxy)-2-<(1S,2R)-3-(tert-butyldiphenylsilyloxy)-1,2-dihydroxypropyl>piperidin-6-one 
• 119011-35-7 (+)-(4R,cis)(Z)-2,2-dimethyl-5-(4-carbethoxy-1-butenyl)-1,3-dioxolane-4-methanol p-toluenesulfonate 
• 1293847-21-8 (4'S,5'R,E)-5-(5'-hydroxymethyl-2',2'-dimethyl[1',3']dioxolan-4'-yl)pent-4-enoic acid methyl ester 
• 1293847-12-7 C₁₂H₁₈O₅ 
• 1293847-13-8 C₁₂H₁₈O₆ 
• 1293847-16-1 (4'S,5'S,E)-5-(5'-methoxycarbamoyl-2',2'-dimethyl[1',3']dioxolan-4'-yl)pent-4-enoic acid methyl ester 

Downstream Products

• 107794-66-1 Benzoic acid (3aR,8aS,9S,9aR)-2,2-dimethyl-octahydro-[1,3]dioxolo[4,5-f]indolizin-9-yl ester 
• 107794-67-2 Benzoic acid (3aR,9R,9aR,9bS)-2,2-dimethyl-octahydro-[1,3]dioxolo[4,5-a]indolizin-9-yl ester 
• 72741-87-8 (1S,2R,8S,8aS)-octahydro-1,2,8-indolizidinetriol 
• 72741-87-8 swainsonine 

Relevant articles and documents

Scale-up synthesis of swainsonine: A potent #-mannosidase II inhibitor

The large-scale synthesis of Swainsonine 1, a potent α-mannosidase II inhibitor, has been achieved with several improvements. The key modifications were (a) performing the Wittig olefination under mild conditions and isolation of the product 4 with modified workup conditions, (b) introduction of the azido group on a large scale under Mitsunobu conditions to produce 12, (c) performing the 1,3-dipolar cycloaddition of an unactivated azide 12 to afford the imino carboxylic ester 7, (d) formation of amide 10 from 7 under mild acidic conditions, and (e) isolation of the final compound 1 as a stable hydrochloride salt. In addition, synthesis of 11 was accomplished from 12 by telescoping the four steps.

Intramolecular 5-endo-trig aminopalladation of β-hydroxy-γ- alkenylamine: Efficient route to a pyrrolidine ring and its application for the synthesis of (-)-8,8a-di-epi-swainsonine

The intramolecular aminopalladation reaction of l-serine derived β-hydroxy-γ-alkenylamines undergoes 5-endo-trig cyclization to furnish pyrrolidine rings in high yields. The pyrrolidines thus obtained were used in the synthesis of (-)-8,8a-di-epi-swainsonine, a specific and competitive inhibitor (Ki value 2 × 10-6 M) of lysosomal α-mannosidases.

Nitrenium ion-mediated alkene bis-cyclofunctionalization: Total synthesis of (-)-swainsonine

Chemical equations presented. The total synthesis of (-)-swainsonine from 2,3-O-isopropylidene-d-erythrose in 12 steps and an overall yield of 28% is reported. The pivotal transformation in our route to this indolizidine alkaloid is the formation of the pyrrolidine ring and C-8a/8 stereodiad through the diastereoselective, bis-cyclofunctionalization of an γ,ss-unsaturated O-alkyl hydroxamate. This transformation is believed to proceed via the intramolecular capture of an N-acyl-N-alkoxyaziridinium ion generated by the diastereoselective addition of a singlet acylnitrenium ion to the pendant alkene.