149198-05-0

Basic information

• Product Name: (2R,5S)-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran-2-carbonitrile
• Synonyms: (2R,5S)-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran-2-carbonitrile
• CAS NO: 149198-05-0
• Molecular Weight: 365.547
• Mol File: 149198-05-0.mol

Chemical Properties

• CAS DataBase Reference: (2R,5S)-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran-2-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,5S)-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran-2-carbonitrile(149198-05-0)
• EPA Substance Registry System: (2R,5S)-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran-2-carbonitrile(149198-05-0)

Safety Data

• Hazardous Substances Data: 149198-05-0(Hazardous Substances Data)

Upstream product

• 201472-26-6 (2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-2-ol 
• 102717-29-3 (5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 
• 21461-84-7 (2S)-tetrahydro-5-oxofuran-2-carboxylic acid 
• 7677-24-9 trimethylsilyl cyanide 
• 201536-71-2 1-acetoxy-2,3-dideoxy-5-O-<(1,1-dimethylethyl)diphenylsilyl>-D-glycero-pentofuranose 

Downstream Products

• 473535-34-1 (2R,5S)-2-(1-oxoethyl)-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran 
• 473535-45-4 (6R)-6-methyl-6-[(2R,5S)-5-([(1,1-dimethyl)ethyldiphenylsilyloxy]methyl)tetrahydrofuran-2-yl]pyran-2[3H]-one 
• 473535-46-5 6R-4,5-dihydro-6-methyl-6-[2R,5S-5-([(1,1-dimethyl-ethyl)diphenylsilanyloxy]methyl)-tetrahydro-furan-2-yl]pyran-3[3H]-one 
• 473535-42-1 (2R,5S)-2-[(R)-2-(2-oxopropyloxy)-3-butyn-2-yl]-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran 
• 473535-41-0 (2R,5S)-2-[(R)-2-(2-methyl-3-propenyloxy)-3-butyn-2-yl]-5-([(1,1-dimethyl)ethyldiphenylsilyl]oxymethyl)tetrahydrofuran 
• 194280-09-6 5-[(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-3,6-bis-trifluoromethyl-[1,2,4]triazine 
• 194280-07-4 (2R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-carboximidic acid methyl ester 
• 165449-97-8 (2R,5S)-5-<(tert-butyldiphenylsiloxy)methyl>tetrahydrofuran-2-methanol 

Relevant articles and documents

Synthetic approach to analogues of the original structure of sclerophytin A

A route to analogues of the original structure of sclerophytin A is described. The β-anomer of dideoxyribosyl nitriles 10a,b (prepared from glutamic acid) was converted into the methyl ketone 11. Addition of a silylated acetylide to 11 in diethyl ether/trimethylamine gave mainly 22a. Alkylation with methallyl halide and ozonolysis gave the ketone 24, which was then converted by hydrogenation and a second ozonolysis into the keto aldehyde 26. A two-step aldol process afforded the desired 3-pyrone 27 in good overall yield. However, several methods for the conversion of this enone 27 into the desired sclerophytin analogue 2 failed.

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.