1273005-86-9

Basic information

• Product Name: (S)-N-[2-(hydroxymethyl)but-3-ynyl]-4-methylbenzenesulfonamide
• Synonyms: (S)-N-[2-(hydroxymethyl)but-3-ynyl]-4-methylbenzenesulfonamide
• CAS NO: 1273005-86-9
• Molecular Weight: 253.322
• Mol File: 1273005-86-9.mol

Chemical Properties

• CAS DataBase Reference: (S)-N-[2-(hydroxymethyl)but-3-ynyl]-4-methylbenzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-[2-(hydroxymethyl)but-3-ynyl]-4-methylbenzenesulfonamide(1273005-86-9)
• EPA Substance Registry System: (S)-N-[2-(hydroxymethyl)but-3-ynyl]-4-methylbenzenesulfonamide(1273005-86-9)

Safety Data

• Hazardous Substances Data: 1273005-86-9(Hazardous Substances Data)

Upstream product

• 50-00-0 formaldehyd 
• 742078-20-2 (2R)-2-ethynyl-N-(4-methylphenylsulfonyl)aziridine 

Downstream Products

• 1273005-95-0 1-(4-bromo-1-tosyl-1H-indol-3-yl)-4-[(2R,5S)-2-phenyl-3-tosyl-1,3-oxazinan-5-yl]but-3-yn-2-one 
• 1273006-07-7 (R)-1-(4-bromo-1-tosyl-1H-indol-3-yl)-4-[(2R,5S)-2-phenyl-3-tosyl-1,3-oxazinan-5-yl]but-3-yn-2-ol 
• 1273006-13-5 (S)-1-(4-bromo-1-tosyl-1H-indol-3-yl)-4-[(2R,5S)-2-phenyl-3-tosyl-1,3-oxazinan-5-yl]but-3-yn-2-ol 
• 1273005-90-5 (2R,5S)-5-(iodoethynyl)-2-phenyl-3-tosyl-1,3-oxazinane 
• 1273005-88-1 (2R,5S)-5-ethynyl-2-phenyl-3-tosyl-1,3-oxazinane 
• 1310737-17-7 (S,Z)-N-[6-(4-bromo-1-tosyl-1H-indol-3-yl)-2-(hydroxymethyl)hex-5-en-3-yn-1-yl]-4-methylbenzenesulfonamide 

Relevant articles and documents

Enantioselective total synthesis of (+)-lysergic acid, (+)-lysergol, and (+)-isolysergol by palladium-catalyzed domino cyclization of allenes bearing amino and bromoindolyl groups

Enantioselective total synthesis of the biologically important indole alkaloids (+)-lysergol, (+)-isolysergol, and (+)-lysergic acid is described. Key features of these total synthesis include (1) a facile synthesis of a chiral 1,3-amino alcohol via the Pd(0)- and In(I)-mediated reductive coupling reaction between l-serine-derived 2-ethynylaziridine and formaldehyde; (2) the Cr(II)/Ni(0)-mediated Nozaki-Hiyama-Kishi (NHK) reaction of an indole-3-acetaldehyde with iodoalkyne; and (3) Pd(0)-catalyzed domino cyclization of an allene bearing amino and bromoindolyl groups. This domino cyclization enabled direct construction of the C/D ring system of the ergot alkaloids skeleton, as well as the creation of the C5 stereogenic center with transfer of the allenic axial chirality to the central chirality.