83482-71-7

Basic information

• Product Name: N(a)-methylthiomethyl-2-deoxoisopteropodine
• Synonyms: N(a)-methylthiomethyl-2-deoxoisopteropodine
• CAS NO: 83482-71-7
• Molecular Weight: 414.569
• Mol File: 83482-71-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N(a)-methylthiomethyl-2-deoxoisopteropodine(CAS DataBase Reference)
• NIST Chemistry Reference: N(a)-methylthiomethyl-2-deoxoisopteropodine(83482-71-7)
• EPA Substance Registry System: N(a)-methylthiomethyl-2-deoxoisopteropodine(83482-71-7)

Safety Data

• Hazardous Substances Data: 83482-71-7(Hazardous Substances Data)

Upstream product

• 67-68-5 dimethyl sulfoxide 
• 83541-47-3 2-deoxoisopteropodine 
• 83541-46-2 2-deoxopteropodine 

Relevant articles and documents

Transformation of Indole Alkaloids. VI. A Novel Conversion of Oxindole Alkaloids into Indole Alkaloids via Indoline Derivatives

Oxindole alkaloids chosen as starting materials were isopteropodine (1a) pteropodine (1b) isoformosanine (7a) and formosanine (7b).Reduction of the iminoethers prepared from the oxindole alkaloids with Et3O(1+)*BF4(1-), with NaBH3(OAc) or with NaBH4/SnCl4*2Et2O afforded the indoline derivatives (3a, 3b, 9a, 9b).The configuration at C7 of 3a, b was determined by NMR analysis of the N(a)-acetyl-N(b)-oxides (6a, b).The signals of H-14β were observed at high field (δ 0.5-1.0) owing to the shielding effect of the aromatic ring in all A type compounds studied.Oxidative conversion of the indolines to indole alkaloids was achieved by using MnO2 or Me2SO/(COCl)2/Et3N as oxidizing agents, and the latter reagent gave better results than the former.Tetrahydroalstonine (11) and akuammigine (12) were obtained from 3a, b, and 19-epiajmalicine (14) and 3-iso-19-epiajmalicine (15) from 9a, b.The A type compounds were more susceptible than the B type compounds to the present reduction and oxidation sequence.Keywords: transformation; oxindole alkaloids; indole alkaloids; heteroyohimbines; reduction; oxidation; dimethyl sulfoxide-oxalyl chloride; indoline