619328-34-6

Basic information

• Product Name: (4S,2'S,3'S,5'S)-3-(7'-benzyloxy-2',3',5'-trimethylheptanoyl)-4-phenyloxazolidin-2-one
• Synonyms: (4S,2'S,3'S,5'S)-3-(7'-benzyloxy-2',3',5'-trimethylheptanoyl)-4-phenyloxazolidin-2-one
• CAS NO: 619328-34-6
• Molecular Weight: 423.552
• Mol File: 619328-34-6.mol

Chemical Properties

• CAS DataBase Reference: (4S,2'S,3'S,5'S)-3-(7'-benzyloxy-2',3',5'-trimethylheptanoyl)-4-phenyloxazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,2'S,3'S,5'S)-3-(7'-benzyloxy-2',3',5'-trimethylheptanoyl)-4-phenyloxazolidin-2-one(619328-34-6)
• EPA Substance Registry System: (4S,2'S,3'S,5'S)-3-(7'-benzyloxy-2',3',5'-trimethylheptanoyl)-4-phenyloxazolidin-2-one(619328-34-6)

Safety Data

• Hazardous Substances Data: 619328-34-6(Hazardous Substances Data)

Upstream product

• 111292-75-2 (4S)-3-((2E)-2-butenoyl)-4-phenyl-1,3-oxazolidin-2-one 
• 88409-08-9 (2R)-4-benzyloxy-1-bromo-2-methylbutane 
• 74-88-4 methyl iodide 
• 754239-29-7 (3'S,4S,5'S)-3-(7'-benzyloxy-3',5'-dimethylheptanoyl)-4-phenyloxazolidin-2-one 
• 619328-33-5 (1'S,2'S,2R)-4-benzyloxy-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-2,N-dimethylbutyramide 
• 96154-47-1 (R)-2-methyl-1,4-butanediol 4-benzyl ether 
• 54555-84-9 benzyl iodoethyl ether 

Downstream Products

• 247184-89-0 (+)-kalkitoxin 
• 619328-35-7 (4S,2'S,3'S,5'S)-3-(7'-oxo-2',3',5'-trimethylheptanoyl)-4-phenyloxazolidin-2-one 
• 619328-36-8 (4S,2'S,3'S,5'S)-3-(7'-methylamino-2',3',5'-trimethylheptanoyl)-4-phenyloxazolidin-2-one 
• 619328-37-9 (2R,3'S,5'S,6'S,4''S)-2,N-dimethyl-N-[3',5',6'-trimethyl-7'-oxo-7'-(2''-oxo-4''-phenyloxazolidin-3-yl)heptyl]butyramide 
• 619328-42-6 (1''R,2'R,3R,4S,6S)-3,4,6-trimethyl-8-[methyl-(2'-methylbutyryl)amino]octanoic acid (1''-benzylsulfanylmethylallyl)amide 
• 619328-44-8 (4S,2'S,3'S,5'S)-3-(7'-hydroxy-2',3',5'-trimethylheptanoyl)-4-phenyloxazolidin-2-one 

Relevant articles and documents

Total synthesis and biological evaluation of (+)-kalkitoxin, a cytotoxic metabolite of the cyanobacterium Lyngbya majuscula

(+)-Kalkitoxin, a metabolite of the marine cyanobacterium Lyngbya majuscula, was synthesized from (R)-2-methylbutyric acid, (R)-cysteine, and (3S, 4S, 6S)-3,4,6-trimethyl-8-(methylamino)octanoic acid. A key step in the synthesis was installation of the anti,anti methyl stereotriad by means of a tandem asymmetric conjugate addition of an organocopper species to an α,β-unsaturated N-acyl oxazolidin-2-one followed in situ by α-methylation of the resultant enolate. The thiazoline portion of kalkitoxin was assembled by titanium tetrachloride catalyzed cyclization of a vinyl substituted amido thiol.

Total synthesis of (+)-kalkitoxin

The neurotoxic lipopeptide (+)-kalkitoxin was synthesized by a route which employed asymmetric organocopper conjugate addition followed by in situ enolate alkylation to install the anti,anti-1,2,4-trimethyl relationship of the toxin; the synthesis of kalkitoxin required sixteen steps and proceeded in 3% overall yield.