L-(+)-SWAINSONINE

Base Information

• Chemical Name: L-(+)-SWAINSONINE
• CAS No.: 164907-52-2
• Molecular Formula: C₈H₁₅NO₃
• Molecular Weight: 173.212
• Mol file: 164907-52-2.mol

Synonyms:1,2,8-Indolizinetriol,octahydro-, [1R-(1a,2a,8b,8ab)]- (9CI); (+)-Swainsonine; L-Swainsonine

Chemical Property of L-(+)-SWAINSONINE

Chemical Property:

• PSA: 63.93000
• LogP: -1.51500
• Storage Temp.: 2-8°C

Purity/Quality:

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37

MSDS Files:

Useful:

Technology Process of L-(+)-SWAINSONINE

There total 42 articles about L-(+)-SWAINSONINE 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: 95.0%

(3aS,9S,9aS,9bR)-octahydro-2,2-dimethyl-[1,3]dioxolo[4,5-a]indolizin-9-ol (886852-68-2) → L-swainsonine (164907-52-2)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/ol0602811 DOI:10.1016/j.tet.2007.10.109

Reference yield: 94.0%

(1R,2S,8S,8aR)-8-(tert-butyldimethylsilyloxy)octahydroindolizine-1,2-diol (1263482-22-9) → L-swainsonine (164907-52-2)

Guidance literature:

With Dowex 50W-X₈ (H(+) form); In methanol; at 20 ℃; for 24h;

DOI:10.1039/c0ob00388c

Reference yield: 94.0%

C13H25NO5 → L-swainsonine (164907-52-2)

Guidance literature:

With hydrogenchloride; palladium on activated charcoal; hydrogen; In ethanol; enantioselective reaction;

DOI:10.1039/c4ra11978a

upstream raw materials:

(3aS,9S,9aS,9bR)-octahydro-2,2-dimethyl-[1,3]dioxolo[4,5-a]indolizin-9-ol

3-((2S,3R,4R,5R,6R)-3-azido-6-(benzyloxy)-tetrahydro-4,5-dihydroxy-2H-pyran-2-yl)propyl methanesulfonate

(2S)-6-hydroxy-2-(3-tert-butyldimethylsilyloxypropyl)-2H-pyran-3(6H)-one

(S)-1-(furan-2-yl)-4-tert-butyldimethylsilyloxybutan-1-ol

Refernces

• 1、 Si, Chang-Mei,Mao, Zhuo-Ya,Dong, Han-Qing,Du, Zhen-Ting,Wei, Bang-Guo,Lin, Guo-Qiang. "Divergent method to trans -5-hydroxy-6-alkynyl/alkenyl-2-piperidinones: Syntheses of (-)-epiquinamide and (+)-swainsonine". . p. 5824 - 5833. Retrieved 2015.
• 2、 Archibald, Glenn,Lin, Chih-Pei,Boyd, Peter,Barker, David,Caprio, Vittorio. "A divergent approach to 3-piperidinols: A concise syntheses of (+)-swainsonine and access to the 1-substituted quinolizidine skeleton". . p. 7968 - 7980. Retrieved 2013/01/15.