Turneforcidine

Base Information

• Chemical Name: Turneforcidine
• CAS No.: 21850-67-9
• Molecular Formula: C8H15NO2
• Molecular Weight: 157.2102
• Mol file: 21850-67-9.mol

Synonyms:(1R,7R,8R)-7-(hydroxy)-1-(hydroxymethyl)pyrrolizidine;(1R,7R,7aR)-7-Hydroxymethyl-hexahydro-pyrrolizin-1-ol;(1R,7R,7aR)-1-Hydroxymethyl-7-hydroxyhexahydro-1H-pyrrolizine;(1S,7R,7aS)-1-Hydroxymethyl-7-hydroxyhexahydro-1H-pyrrolizine;(1S,7R,7aR)-1-Hydroxymethyl-7-hydroxyhexahydro-1H-pyrrolizine;(7aR)-7c-Hydroxymethyl-(7ar)-hexahydro-pyrrolizin-1t-ol;

Chemical Property of Turneforcidine

Chemical Property:

• Melting Point: 118.5-l20°C
• PSA: 43.70000
• LogP: -0.62830

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: This alkaloid has been found in small quantities in the extract from Turneforcia sibirica. lt crystallizes as colourless needles from Me2CO and has [α]D - 10.5°. lt appears probable that it is an artifact formed by hydrolysis of Turneforcine (q.v.) during the extraction process.

Technology Process of Turneforcidine

There total 30 articles about Turneforcidine 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: 75.0%

(1R,7R,7aR)-7-Hydroxy-hexahydro-pyrrolizine-1-carboxylic acid methyl ester (25471-74-3) → (-)-turneforcidine (21850-67-9)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 4h; Heating;

DOI:10.1021/jo00223a002

Reference yield: 68.0%

(1R,7R,8R)-7-(tert-butyldiphenylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)pyrrolizidine (328404-70-2) → (-)-turneforcidine (21850-67-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/S0040-4039(00)01664-6

Reference yield: 40.0%

ethyl (1R*,7aR*)-(+/-)-7-oxo-2,3,5,6,7,7a-hexahydro-1H-pyrrolizine-1-carboxylate → (+/-)-hastanecine (480-84-2,520-62-7,21824-59-9,21824-60-2,21850-67-9,36066-93-0,51370-96-8,65026-66-6,65207-60-5,83946-88-7,86258-53-9,113427-38-6) + (+/-)-turneforcidine (83946-88-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1246/bcsj.70.2541

upstream raw materials:

cropodine

(1R,7R,7aR)-7-Hydroxy-hexahydro-pyrrolizine-1-carboxylic acid methyl ester

(1R,7R,8R)-7-(tert-butyldiphenylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)pyrrolizidine

(1R,5R)-(-)-6-aza-6-benzyloxycarbonyl-2-oxabicyclo[3.3.0]octan-3-one

Refernces

• 1、 Brambilla, Marta,Davies, Stephen G.,Fletcher, Ai M.,Roberts, Paul M.,Thomson, James E.. "Asymmetric syntheses of (?)-hastanecine, (?)-turneforcidine and (?)-platynecine". . p. 4523 - 4535. Retrieved 2016.
• 2、 Wee. "A dirhodium(II)-carbenoid route to (-)- and (+)-Geissman-Waiss lactone: Synthesis of (1R,7R,8R)-(-)-turneforcidine". . p. 8513 - 8517. Retrieved 2007/10/03.