149099-16-1

Basic information

• Product Name: (2R,5S,2'S,5'S)-5-<5'-<(tert-Butyldiphenylsiloxy)methyl>tetrahydrofuran-2'-yl>-1,2-O-isopropylidenepentane-1,2,5-triol
• Synonyms: (2R,5S,2'S,5'S)-5-<5'-<(tert-Butyldiphenylsiloxy)methyl>tetrahydrofuran-2'-yl>-1,2-O-isopropylidenepentane-1,2,5-triol
• CAS NO: 149099-16-1
• Molecular Weight: 498.735
• Mol File: 149099-16-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2R,5S,2'S,5'S)-5-<5'-<(tert-Butyldiphenylsiloxy)methyl>tetrahydrofuran-2'-yl>-1,2-O-isopropylidenepentane-1,2,5-triol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,5S,2'S,5'S)-5-<5'-<(tert-Butyldiphenylsiloxy)methyl>tetrahydrofuran-2'-yl>-1,2-O-isopropylidenepentane-1,2,5-triol(149099-16-1)
• EPA Substance Registry System: (2R,5S,2'S,5'S)-5-<5'-<(tert-Butyldiphenylsiloxy)methyl>tetrahydrofuran-2'-yl>-1,2-O-isopropylidenepentane-1,2,5-triol(149099-16-1)

Safety Data

• Hazardous Substances Data: 149099-16-1(Hazardous Substances Data)

Upstream product

• 96392-13-1 (2R)-4-Bromo-1,2-O-isopropylidenebutane-1,2-diol 
• 149099-14-9 (2S,5S)-5-<(tert-Butyldiphenylsiloxy)methyl>tetrahydrofuran-2-carboxaldehyde 
• 149099-13-8 (2S,5S)-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran-2-carbonitrile 
• 170305-51-8 Methyl (2S,5S)-5-<(tert-Butyldiphenylsiloxy)methyl>tetrahydrofuran-2-carboxylate 
• 201536-71-2 1-acetoxy-2,3-dideoxy-5-O-<(1,1-dimethylethyl)diphenylsilyl>-D-glycero-pentofuranose 
• 165657-74-9 (2R)-4-iodo-1,2-O-isopropylidenebutane-1,2-diol 
• 201472-26-6 (2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-2-ol 
• 165657-75-0 (4R)-2-(2,2-Dimethyl-1,3-dioxolan-4-yl)ethyl 4-methylbenzenesulfonate 
• 5754-34-7 2-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol 
• 102717-29-3 (5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one 

Downstream Products

• 157732-26-8 (2S,5S,2'S,5'S)-5-<5'-<(tert-Butyldiphenylsiloxy)methyl>tetrahydrofuran-2'-yl>tetrahydrofuran-2-carboxaldehyde 
• 149099-19-4 (2S,5S,2'S,5'S,2''S,5''S)-5-<5'-<5''-<(tert-Butyldiphenylsiloxy)methyl>tetrahydrofuran-2''-yl>tetrahydrofuran-2'-yl>tetrahydrofuran-2-methanol 
• 149099-18-3 (2R,5S,2'S,5'S,2''S,5''S)-1,2-O-Isopropylidene-5-<5'-<5''-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran-2''-yl>tetrahydrofuran-2'-yl>pentane-1,2,5-triol 
• 149099-17-2 (2S,5S,2'S,5'S)-5-<5'-<(tert-Butyldiphenylsiloxy)methyl>tetrahydrofuran-2'-yl>tetrahydrofuran-2-methanol 
• 170553-09-0 (2R,5S,2'S,5'S)-5-<5'-<(tert-Butyldiphenylsiloxy)methyl>tetrahydrofuran-2'-yl>pentane-1,2,5-triol 

Relevant articles and documents

Stereoselective Synthesis of Oligo(tetrahydrofurans): Linear and Convergent Routes to Bi- and Tetrahydrofurans

The "dimeric" and "trimeric" oligo(tetrahydrofurans) (oligo-THFs) 24, 28, 32, and 38 were synthesized stereoselectively according to a linear and a convergent synthetic strategy.The oligo-THFs thus obtained are important intermediates for the synthesis of artificial ion channels.Furthermore, they can be used in the total synthesis of Annonaceae acetogenins, a class of natural occurring oligo-THFs with promising pharmacological properties. - Keywords: Synthesis, stereoselective / Oligo(tetrahydrofurans), natural, non-natural /Ion channels, artificial / Annonaceae acetogenins

Tetrahydrofuran-podands, stereoselective synthesis of trans-2,5-oligo-tetrahydrofurans

Enantiomerically pure THF-podands 1 were synthesized along a linear route starting from lactone 3. A high degree of stereochemical control was achieved by chelation controlled addition of the functionalized Grignard reagent 7 to α-alkoxy-aldehydes of type 6.