474671-04-0

Basic information

• Product Name: (R)-2-Oxo-5-prop-2-ynyl-oxazolidine-3-carboxylic acid methyl-(2-nitro-benzyl)-amide
• Synonyms: (R)-2-Oxo-5-prop-2-ynyl-oxazolidine-3-carboxylic acid methyl-(2-nitro-benzyl)-amide
• CAS NO: 474671-04-0
• Molecular Weight: 317.301
• Mol File: 474671-04-0.mol

Chemical Properties

• CAS DataBase Reference: (R)-2-Oxo-5-prop-2-ynyl-oxazolidine-3-carboxylic acid methyl-(2-nitro-benzyl)-amide(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-Oxo-5-prop-2-ynyl-oxazolidine-3-carboxylic acid methyl-(2-nitro-benzyl)-amide(474671-04-0)
• EPA Substance Registry System: (R)-2-Oxo-5-prop-2-ynyl-oxazolidine-3-carboxylic acid methyl-(2-nitro-benzyl)-amide(474671-04-0)

Safety Data

• Hazardous Substances Data: 474671-04-0(Hazardous Substances Data)

Upstream product

• 474671-00-6 (4R)-5-azido-4-hydroxy-1-(trimethylsilyl)pent-1-yne 
• 455312-10-4 (R)-5-(3-Trimethylsilanyl-prop-2-ynyl)-oxazolidin-2-one 
• 211619-36-2 N-methyl-N-(2-nitrobenzyl)carbamoyl chloride 
• 143724-89-4 Trimethyl-((R)-3-oxiranyl-prop-1-ynyl)-silane 
• 474671-03-9 (R)-2-Oxo-5-(3-trimethylsilanyl-prop-2-ynyl)-oxazolidine-3-carboxylic acid methyl-(2-nitro-benzyl)-amide 

Downstream Products

• 455312-08-0 (3aS,4S,5S,6aR)-4-[(2-Nitro-benzyl)-(1H-pyrrole-2-carbonyl)-amino]-2-oxo-5-(toluene-4-sulfonyl)-tetrahydro-cyclopentaoxazole-3-carboxylic acid methyl-(2-nitro-benzyl)-amide 
• 455312-13-7 1H-Pyrrole-2-carboxylic acid [(1S,2S,3R,5S)-3-hydroxy-2-[3-methyl-3-(2-nitro-benzyl)-ureido]-5-(toluene-4-sulfonyl)-cyclopentyl]-(2-nitro-benzyl)-amide 
• 474671-05-1 (3aS,4S,5S,6aR)-4-(2-Nitro-benzylamino)-2-oxo-5-(toluene-4-sulfonyl)-tetrahydro-cyclopentaoxazole-3-carboxylic acid methyl-(2-nitro-benzyl)-amide 
• 455312-14-8 1-methyl-1-(2-nitro-benzyl)-3-[4-(2-nitro-benzyl)-2,5-dioxo-2,3,3a,4,5,8b-hexahydro-1H-4,8a-diaza-as-indacen-3-yl]-urea 
• 455312-09-1 (3aS,6aR)-2-Oxo-5-(toluene-4-sulfonyl)-6,6a-dihydro-3aH-cyclopentaoxazole-3-carboxylic acid methyl-(2-nitro-benzyl)-amide 

Relevant articles and documents

Alkynyliodonium salts in organic synthesis. Development of a unified strategy for the syntheses of (-)-agelastatin A and (-)-agelastatin B

The total syntheses of natural agelastatin A and agelastatin B were accomplished via a strategy that utilized an alkynyliodonium salt → alkylidenecarbene → cyclopentene transformation to convert a relatively simple amino alcohol derivative to the functionalized core of the agelastatin system. Subsequent manipulations delivered debromoagelastatin, which served as a precursor to both agelastatin A and agelastatin B. Alkylidenecarbene insertion chemoselectivity issues were explored en route to the final targets.

Alkynyliodonium salts in organic synthesis. Application to the total synthesis of (-)-Agelastatin A and (-)-Agelastatin B

The asymmetric total syntheses of (-)-agelastatin A and (-)-agelastatin B were accomplished in 14 steps each from (R)-epichlorohydrin. The pivotal transformation in both sequences was a sulfinate-promoted cyclization of an alkynyliodonium salt to furnish