121469-47-4

Basic information

• Product Name: (2S,3S)-1-p-toluenesulfonyl-4-buten-1,2,3-triol
• Synonyms: (2S,3S)-1-p-toluenesulfonyl-4-buten-1,2,3-triol
• CAS NO: 121469-47-4
• Molecular Weight: 272.322
• Mol File: 121469-47-4.mol

Chemical Properties

• CAS DataBase Reference: (2S,3S)-1-p-toluenesulfonyl-4-buten-1,2,3-triol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-1-p-toluenesulfonyl-4-buten-1,2,3-triol(121469-47-4)
• EPA Substance Registry System: (2S,3S)-1-p-toluenesulfonyl-4-buten-1,2,3-triol(121469-47-4)

Safety Data

• Hazardous Substances Data: 121469-47-4(Hazardous Substances Data)

Upstream product

• 121469-49-6 [(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]methyl 4-methyl-benzenesulfonate 
• 121405-01-4 (-)-(2S,3S)-2,3-Epoxy-1-tosyloxypent-4-ene 
• 4949-20-6 (E)-2,4-pentadien-1-ol 
• 121405-00-3 (+/-)-2,3-Epoxy-1-tosyloxypent-4-ene 
• 78260-12-5 (+/-)-2,3-Epoxypent-4-en-1-ol 
• 121405-04-7 (+/-)-4-Tosyloxymethyl-5-vinyl-1,3-dioxolan-2-one 
• 99902-68-8 (+/-)-2,2-Dimethyl-4-tosyloxymethyl-5-vinyl-1,3-dioxolane 
• 287934-61-6 (2R)-4-pentene-1,2,3-triol 
• 98-59-9 p-toluenesulfonyl chloride 
• 121521-25-3 (-)-(2S,3S)-2,3-epoxypent-4-en-1-ol 
• 207123-21-5 (S,S)-2,2-dimethyl-4-[(tert-butyldimethylsilyloxy)methyl]-5-vinyl-1,3-dioxolane 
• 212579-64-1 (4R)-1-(2,2-dimethyl-[1,3]dioxolan-4-yl)allyl alcohol 

Downstream Products

• 121469-49-6 [(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]methyl 4-methyl-benzenesulfonate 
• 100017-25-2 (4S,5R)-2,2-dimethyl-4-(p-toluenesulfonyloxy)methyl-5-vinyl-1,3-dioxolane 
• 121405-02-5 (+/-)-(2S,4R,5S)-2-Methyl-2-<2-(phenylsulfonyl)ethyl>-4-tosyloxymethyl-5-vinyl-1,3-dioxolane 
• 121405-03-6 (+/-)-(1R,5S,7S)-5-Methyl-3-phenylsulfonyl-7-vinyl-6,8-dioxabicyclo<3.2.1>octane 
• 99902-68-8 (+/-)-2,2-Dimethyl-4-tosyloxymethyl-5-vinyl-1,3-dioxolane 
• 121405-06-9 (+/-)-2,2-Dimethyl-4-<2-phenylsulfonyl-3-(2-methyl-1,3-dioxolan-2-yl)propyl>-5-vinyl-1,3-dioxolane 
• 121405-06-9 (-)-(4S,5S)-2,2-Dimethyl-4-<2-phenylsulfonyl-3-(2-methyl-1,3-dioxolan-2-yl)propyl>-5-vinyl-1,3-dioxolane 
• 249603-93-8 (3S,4S)-3,4-bis(tert-butyldimethylsiloxy)-8-phenyloct-1-en-7-yne 
• 249603-95-0 (3S,4S)-3,4-(di-tert-butylsilylenedioxy)-8-phenyloct-1-en-7-yne 
• 249603-94-9 (3S,4S)-8-phenyloct-1-en-7-yne-3,4-diol 

Relevant articles and documents

Stereocomplementary Construction of Optically Active Bicyclo[4.3.0]nonenone Derivatives

Treatment of (5S,6S)-5,6-bis(tert-butyldimethylsiloxy)-8-(substituted)oct-1-en-7-yne derivatives, prepared from diethyl L-tartrate, with Co2(CO)8 afforded the corresponding cobalt-complexed enynes, which were subsequently exposed to the typical Pauson-Khand conditions to furnish highly stereoselectively or exclusively (2S,3S,6S)-2,3-bis(tert-butyldimethylsiloxy)-9-(substituted)bicyclo-[4.3.0]non- 1(9)-en-8-ones. On the other hand, (3S,4S)-1-(substituted)oct-7-en-1-yne-3,4-diol congeners produced, on exposure to the Pauson-Khand conditions, (2S,3S,6A)-2,3-dihydroxy-9-(substituted)-bicyclo[4.3.0]-non-1(9)-en-8-one derivatives in a highly stereoselective manner. The newly developed procedure has been shown to be useful for construction of the 2,3-bis(oxygenated)-7-(substituted)-bicyclo[4.3.0]non-6-en-8-one framework in a stereocomplementary as well as stereoselective fashion.

ASYMMETRIC SHARPLESS EPOXIDATION OF DIVINYLCARBINOL. erythro-D- AND -L-4-PENTENITOLS BY HYDROLYSIS OF REGIOISOMERIC EPOXY-4-PENTENOLS

The asymmetric Sharpless epoxidation of divinylcarbinol (1), a secondary, achiral allylic alcohol, is described in detail.The epoxidation proceeds with high enantio-control and diastereo-selection.The resulting 1,2-epoxy-4-pentene-3-ols 2 are equilibrated to afford the internal epoxides 5.Hydrolysis of the regioisomers 2 and 5, respectively, furnishes opposite enantiomers of erythro-4-pentenitols 3 with high selectivity.Several derivatives of 3 are described, as well as result of a less stereoselective route - from D-glyceraldehyde acetonide (10) - providing NMR data of the threo series. - The acute toxicity of divinylcarbinol (1) is reported, along with the mutagenicity of 1, L-2 and L-5 as determined by Ames tests.

Synthesis of Side-Chain Unsaturated endo- and exo-Brevicomins. Representatives of Pheromone Analogs in the Dioxabicyclooctane Series

The title substances endo- and exo-9 were synthesized via selective trans- and cis-opening of the epoxy tosylate 3, respectively.The tosylate 3 is easily obtainable from pentadienol 1.