Castanospermine

Base Information

• Chemical Name: Castanospermine
• CAS No.: 79831-76-8
• Molecular Formula: C8H15 N O4
• Molecular Weight: 189.211
• Hs Code.: 2921290090
• European Community (EC) Number: 616-743-4
• UNII: Q0I3184XM7
• DSSTox Substance ID: DTXSID601026043
• Nikkaji Number: J52.984B
• Wikipedia: Castanospermine
• Wikidata: Q753104
• Metabolomics Workbench ID: 51487
• ChEMBL ID: CHEMBL311226
• Mol file: 79831-76-8.mol

Synonyms:1,6,7,8-tetrahydroxyoctahydroindolizine;1-epicastanospermine;6,7-diepicastanospermine;6-epicastanospermine;castanospermine;castinospermine

Chemical Property of Castanospermine

Chemical Property:

• Appearance/Colour: White Crystalline Solid
• Vapor Pressure: 6.94E-09mmHg at 25°C
• Melting Point: 213-217 °C(lit.)
• Boiling Point: 421.9oC at 760 mmHg
• PKA: 6.09(at 25℃)
• Flash Point: 267.6oC
• PSA: 84.16000
• Density: 1.53g/cm3
• LogP: -2.54420
• Storage Temp.: 2-8°C
• Solubility.: 1 M HCl: 20 mg/mL, clear, very faintly yellow
• Water Solubility.: Soluble in water
• XLogP3: -2.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 189.10010796
• Heavy Atom Count: 13
• Complexity: 201

Purity/Quality:

98%,99%, ^*data from raw suppliers

Castanospermine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CN2CC(C(C(C2C1O)O)O)O
• Isomeric SMILES: C1CN2C[C@@H]([C@H]([C@@H]([C@H]2[C@H]1O)O)O)O
• Description: Glucosidases catalyze the cleavage of individual glucosyl residues from various glycoconjugates, including complex carbohydrates and glycoproteins. Castanospermine is an inhibitor of both α- and β-glucosidases, inhibiting lysosomal and neutral α-glucosidases with Ki values of 0.1 and 10 μM, respectively, and lysosomal and cytosolic β-glucosidases with Ki values of 7 and 40 μM, respectively. It is effective both in vitro and in vivo. Through its effects on glucosidases, castanospermine blocks N-linked glycosylation during post-translational modification of proteins, affecting protein trafficking and cell functions that are dependent on glycosylation, including angiogenesis. Castanospermine also interferes with viral replication and infection that is dependent on glucosidase activity.
• Uses: Castanospermine, is used as a glycosidase inhibitor and antiinflammatory agent.castanospermine is used to inhibit syncytium formation between HIV-infected and CD4-expressing cells and may also interfere with infectivity. It has also been demonstrated that this agent inhibits inflammation at the level of leukocyte extravasation in rat models of experimental adjuvant-induced arthritis and autoimmune encephalomyelitis. Castanospermine is an inhibitor of Glucosidase I, Maltase-glucoamylase, and MANBA. Potent inhibitor of α- and β-glucosidases, especially glucosidase l (required for glucoprotein processing by transfer of mannose and glucose from asparagine-linked lipids). Inhibits HIV syncytium formation and replication. Castanospermine is a plant alkaloid shown to be a potent inhibitor of lysosomal a-or beta- glucosidase. It also inhibits mammalian glucosidase 1 and beta-mannosidase from sweet almonds and fungal beta-xylosidase. a-L-fucosidases inhibitor

Technology Process of Castanospermine

There total 199 articles about Castanospermine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

(1R,6R,7S,8S,8aS)-8-Benzyloxy-octahydro-indolizine-1,6,7-triol (123190-77-2,131722-89-9) → (+/-)-castanospermin (79831-76-8,89955-60-2,107244-34-8,111467-11-9,117894-10-7,117894-11-8,121250-62-2,123284-48-0,129445-66-5,130983-46-9,139014-22-5,139014-23-6,139014-24-7,140386-64-7,140386-65-8,142393-60-0,142394-39-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; water; at 20 ℃; for 24h;

DOI:10.1016/S0040-4039(01)80287-2

Reference yield: 96.0%

(3aR,4S,9S,9aR,9bR)-9-Methoxymethoxy-2,2-dimethyl-octahydro-[1,3]dioxolo[4,5-g]indolizin-4-ol (211570-46-6) → (1S,6S,7R,8R,8aR)-2,6,7,8-tetrahydroxy-indolizidine (79831-76-8)

Guidance literature:

With hydrogenchloride; water; In methanol;

DOI:10.1039/a802741b

Reference yield: 95.0%

(1S,6S,7S,8R,8aS)-6,7-bis(benzyloxy)-octahydroindolizine-1,8-diol (1018472-29-1) → (1S,6S,7R,8R,8aR)-2,6,7,8-tetrahydroxy-indolizidine (79831-76-8)

Guidance literature:

With hydrogen; palladium dichloride; In methanol; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2008.01.073

upstream raw materials:

(1S,6S,7R,8R,8aR)-1-(tert-Butyl-dimethyl-silanyloxy)-7,8-bis-trimethylsilanyloxy-octahydro-indolizin-6-ol

(1S,6S,7S,8R,8aR)-1-hydroxy-6,7,8-tris(benzyloxy)indolizidine

(1S,6S,7R,8R,8aR)-1,6,7,8-tetrahydroxyhexahydroindolizin-3-one

(3aS,8S,8aS,9R,9aS)-8-(tert-Butyl-dimethyl-silanyloxy)-9-hydroxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-f]indolizin-6-one

Downstream raw materials:

Benzoic acid (1S,6S,7R,8R,8aS)-6,7,8-trihydroxy-octahydro-indolizin-1-yl ester

1,6,7,8-tetra-O-acetylcastanospermine

1,6,7-tri-O-benzylcastanospermine

6-O-carboxybenzylcastenospermine

Refernces

• 1、 Furneaux,Mason,Tyler. "The chemistry of castanospermine, part III: e, an unusual route to a novel compound". . p. 3055 - 3058. Retrieved 1995.
• 2、 Liu, Gang,Wu, Tian-Jun,Ruan, Yuan-Ping,Huang, Pei-Qiang. "A flexible approach to azasugars: asymmetric total syntheses of (+)-castanospermine, (+)-7-deoxy-6-epi-castanospermine, and (+)-1-epi- castanospermine". experimental part. p. 5755 - 5768. Retrieved 2010/08/19.
• 3、 Jensen, Thomas,Mikkelsen, Mette,Lauritsen, Anne,Andresen, Thomas L.,Gotfredsen, Charlotte H.,Madsen, Robert. "A concise synthesis of castanospermine by the use of a transannular cyclization". experimental part. p. 8886 - 8889. Retrieved 2010/03/01.