364597-35-3

Basic information

• Product Name: (R)-3-[N-methyl-N-(toluene-4-sulfonyl)amino]hexanal
• Synonyms: (R)-3-[N-methyl-N-(toluene-4-sulfonyl)amino]hexanal
• CAS NO: 364597-35-3
• Molecular Weight: 283.392
• Mol File: 364597-35-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (R)-3-[N-methyl-N-(toluene-4-sulfonyl)amino]hexanal(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-[N-methyl-N-(toluene-4-sulfonyl)amino]hexanal(364597-35-3)
• EPA Substance Registry System: (R)-3-[N-methyl-N-(toluene-4-sulfonyl)amino]hexanal(364597-35-3)

Safety Data

• Hazardous Substances Data: 364597-35-3(Hazardous Substances Data)

Upstream product

• 364597-80-8 tert-butyl (R)-3-(toluene-4-sulfonylamino)hexanoate 
• 364597-34-2 tert-butyl (R)-3-[N-methyl-N-(toluene-4-sulfonyl)amino]hexanoate 
• 217823-12-6 tert-butyl (3R)-3-aminohexanoate 
• 217823-13-7 tert-butyl (3R)-3-aminohexanoate 
• 85144-28-1 tert-butyl (2E)-hex-2-enoate 
• 364597-82-0 (R)-3-[N-methyl-N-(toluene-4-sulfonyl)amino]hexan-1-ol 

Downstream Products

• 1415891-03-0 2,6-dimethylphenyl (2R,3S,4R,5R,8S,10R)-3-tert-butyldimethylsilyloxy-2,4-dimethyl-5,8-epoxy-10-[N-methyl-N-(toluene-4-sulfonyl)amino]tridecanoate 
• 1093402-75-5 (2S,3R,6S,8R)-1-benzyloxy-8-(N-tert-butoxycarbonyl-N-methylamino)-3,6-epoxy-2-methylundecane 
• 1415890-95-7 (2S,3R,6S,8R)-1-benzyloxy-3,6-epoxy-2-methyl-8-(methylamino)undecane 
• 364597-85-3 (2S,3S,4S,6R,8R)-1-benzyloxy-8-[N-methyl-N-(toluene-4-sulfonyl)amino]-3,6-epoxy-2-methyl-4-(phenylseleno)undecane 
• 1415891-06-3 (2S,3S,4R,5R,8S,10R)-2,4-dimethyl-5,8-epoxy-1,3-(carbonyldioxy)-10-[N-methyl-N-(toluene-4-sulfonyl)amino]tridecane 
• 1415891-05-2 C₂₃H₃₉NO₅S 
• 1415891-04-1 (2R,3R,4R,5R,8S,10R)-10-[N-methyl-N-(toluene-4-sulfonyl)amino]-2,3;5,8-bis-epoxy-4-methyltridecan-1-ol 
• 364597-37-5 (2R,6S,8R,3Z)-8-[N-methyl-N-(toluene-4-sulfonyl)amino]-1-benzyloxy-2-methylundec-3-en-6-ol 
• 364597-71-7 benzyl (2S,3R,6S,8S)-8-{(2R,3R,6S,7R,8S,9R,10R,13S,15R)-8-tert-butyldimethylsilyloxy-3,6;10,13-bis-epoxy-15-(N-tert-butyloxycarbonyl-N-methylamino)-2,7,9-trimethyloctadecanoyloxy}-3,6-epoxy-2-methylundecanoate 
• 364597-96-6 benzyl (2S,3R,6S,8S)-8-{(2R,3R,6S,7S,8S,9S,10R,13S,15R)-3,6;10,13-bis-epoxy-15-(N-tert-butyloxycarbonyl-N-methylamino)-8-hydroxy-2,7,9-trimethyloctadecanoyloxy}-3,6-epoxy-2-methylundecanoate 
• 1027299-19-9 N-((R)-1-{(2S,5R)-5-[(1R,2S,3R)-3-[(2S,5S)-5-((S)-2-Benzyloxy-1-methyl-ethyl)-4-phenylselanyl-tetrahydro-furan-2-yl]-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-butyl]-tetrahydro-furan-2-ylmethyl}-butyl)-4,N-dimethyl-benzenesulfonamide 
• 364597-54-6 (2R,6S,7R,8R,9R,10R,13S,15R,3Z)-1-benzyloxy-8-tert-butyldimethylsilyloxy-10,13-epoxy-15-[N-methyl-N-(toluene-4-sulfonyl)amino]-2,7,9-trimethyloctadec-3-en-6-ol 
• 364597-55-7 (2S,3R,6S,7R,8S,9R,10R,13S,15R)-1-benzyloxy-8-tert-butyldimethylsilyloxy-3,6;10,13-bis-epoxy-15-[N-methyl-N-(toluene-4-sulfonyl)amino]-2,7,9-trimethyloctadecane 
• 364597-93-3 (2S,3R,6S,7R,8S,9R,10R,13S,15R)-1-benzyloxy-8-tert-butyldimethylsilyloxy-3,6;10,13-bis-epoxy-15-(N-tert-butyloxycarbonyl-N-methylamino)-2,7,9-trimethyloctadecane 

Relevant articles and documents

Total syntheses of pamamycin 607 and methyl nonactate: Stereoselective cyclisation of homoallylic alcohols that had been prepared with remote stereocontrol using allylstannanes

The tin(iv) chloride mediated cyclisation of (Z)-homoallylic alcohols using phenylselenenyl chloride or phthalimide in the presence of a Lewis acid followed by reductive removal of the phenylselenenyl group was found to give 2,5-cis-disubstituted tetrahydrofurans with excellent stereocontrol. Using this procedure, (2S,4S,8R,6Z)-9-benzyloxy-2-tert-butyldiphenylsilyloxy-8-methylnon-6- en-4-ol (11), prepared stereoselectively via the tin(iv) chloride promoted reaction between the (R)-5-benzyloxy-4-methylpent-2-enyl(tributyl)stannane (3) and (S)-3-tert-butyldiphenylsilyloxybutanal (10), gave (2S,3R,6S,8S)-1- benzyloxy-8-tert-butyldiphenylsilyloxy-3,6-epoxy-2-methylnonane (13) after deselenation. This tetrahydrofuran was selectively deprotected, oxidized and esterified to give methyl nonactate (2). Having established this synthesis of 2,5-cis-disubstituted tetrahydrofurans, it was applied to complete a synthesis of pamamycin 607 (1). (2S,3R,6S,8R)-1-Benzyloxy-8-[N-methyl-N-(toluene-4- sulfonyl)amino]-3,6-epoxy-2-methylundecane (35) was prepared stereoselectively from (R)-3-[N-(toluene-4-sulfonyl)-N-methylamino]hexanal (32) by reaction with the stannane 3 followed by cyclisation of the resulting alkenol 33 and deselenation. Following debenzylation and oxidation, an aldol reaction of the aldehyde 37 using the lithium enolate of 2,6-dimethylphenyl propanoate (61) gave mainly the 2,3-anti-3,4-syn-adduct 48. After protection of the secondary alcohol as its tert-butyldimethylsilyl ether 49, reduction using DIBAL-H and oxidation, the resulting aldehyde, (2S,3S,4R,5R,8S,10R)-3-tert- butyldimethylsilyloxy-2,4-dimethyl-5,8-epoxy-10-[N-methyl-N-(toluene-4-sulfonyl) amino]tridecanal (62), was taken through to the bis-tetrahydrofuran 65 by repeating the sequence of the reactions with the stannane 3, cyclisation and deselenation. The N-(toluene-4-sulfonyl) group was then replaced by an N-(tert-butoxycarbonyl) group and O-debenzylation and oxidation gave the carboxylic acid 70 that corresponds to the C(1)-C(18) fragment of pamamycin 607 (1). Similar chemistry was used to prepare the C(1′)-C(11′) fragment 89 of the pamamycin, except that in this case the configuration of the secondary alcohol introduced by the allylstannane reaction had to be inverted using a Mitsunobu reaction before the cyclisation. Esterification of the carboxylic acid of the C(1)-C(18)-fragment 70 using the alcohol 89 of the C(1′)-C(11′) fragment followed by selective deprotection, macrocyclisation, N-deprotection and N-methylation gave pamamycin 607 (1) that was identical to a sample of the natural product. The Royal Society of Chemistry 2012.