221459-89-8

Basic information

• Product Name: (2RS,5S)-5-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>tetrahydrofuran-2-ol
• Synonyms: (2RS,5S)-5-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>tetrahydrofuran-2-ol
• CAS NO: 221459-89-8
• Molecular Weight: 232.395
• Mol File: 221459-89-8.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (2RS,5S)-5-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>tetrahydrofuran-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2RS,5S)-5-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>tetrahydrofuran-2-ol(221459-89-8)
• EPA Substance Registry System: (2RS,5S)-5-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>tetrahydrofuran-2-ol(221459-89-8)

Safety Data

• Hazardous Substances Data: 221459-89-8(Hazardous Substances Data)

Upstream product

• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 

Downstream Products

• 868700-21-4 1-(3',5'-di-tert-butyl-4'-methoxyphenylsulfanyl)-5-O-(tert-butyldimethylsilyl)-α-D-glycero-pentofuranoside 
• 130948-34-4 4-Amino-1-(2,3-dideoxy-β-D-glyceropentofuranosyl)-1H-imidazo<4,5-c>pyridine 
• 132062-50-1 C₁₂H₁₆N₃O₁₃P₃ 
• 114849-58-0 2-chloro-2',3'-dideoxyadenosine 
• 121154-54-9 2',3'-dideoxy-α-D-uridine 
• 5983-09-5 2',3'-Dideoxyuridine 
• 3416-05-5 3'-Deoxythymidine 
• 221459-13-8 tert-butyl<<(S)-2,3-dihydro-4-(phenylseleno)-2-furyl>methoxy>dimethylsilane 
• 221459-12-7 tert-butyl<<(S)-2,3-dihydro-4-(phenylthio)-2-furyl>methoxy>dimethylsilane 
• 869732-32-1 (2E,8E)-(6S,7S,10S,11R,12S,14R)-15-(3-Benzyloxy-5-bromo-2-methoxy-phenyl)-7-(tert-butyl-dimethyl-silanyloxy)-6,12-dimethoxy-11-methoxymethoxy-2,8,10,14-tetramethyl-pentadeca-2,8-dienoic acid ethyl ester 
• 869732-33-2 (2E,6S,7S,8E,10S,11R,12S,14R)-15-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-7-((tert-butyldimethylsilyl)oxy)-6,12-dimethoxy-11-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,8-dienoic acid 
• 869732-09-2 (2E,6S,7S,8E,10S,11R,12S,14R)-15-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-7-(tert-butyldimethylsilyloxy)-6,12-dimethoxy-11-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,8-dienamide 
• 869732-19-4 (4E,8S,9S,10E,12S,13R,14S,16R)-20-(benzyloxy)-9-(tert-butyldimethylsilyloxy)-13-(methoxymethoxy)-4,10,12,16-tetramethyl-8,14,19-trimethoxy-2-aza-bicyclo[16.3.1]docosa-1⁽²¹⁾,4,10,18⁽²²⁾,19-pentaen-3-one 
• 869732-20-7 (4E,8S,9S,10E,12S,13R,14S,16R)-carbamic acid 20-(benzyloxy)-13-(methoxymethoxy)-4,10,12,16-tetramethyl-8,14,19-trimethoxy-3-oxo-2-azabicyclo[16.3.1]docosa-1⁽²¹⁾,4,10,18⁽²²⁾,19-pentaen-9-yl ester 

Relevant articles and documents

Design and Synthesis of New Acid Cleavable Linkers for DNA Sequencing by Synthesis

A new kind of acid sensitive tetrahydrofuranyl (THF) linker was synthesized and then reacted with 5-(6)-carboxytetramethylrhodaminesuccinimidyl ester (5(6)-TAMRA, SE), followed by di(N-succinimidyl) carbonate (DSC) and modified 2′-deoxyuridine triphosphate (dUTP); the final product, as a reversible terminator for DNA sequencing by synthesis (DNA SBS), was given obtained and confirmed by 1H-NMR, 31P-NMR, and HRMS with purity of up to 99%. The synthesized dye-labeled terminator incorporated into DNA strand successfully, and the fluorophore was cleaved completely under acidic conditions. The preliminary results encourage us to explore more acid-sensitive linkers for DNA SBS to increase the cleavage efficiency under weakly acidic conditions.

Total synthesis of reblastatin

Enantioselective total synthesis of reblastatin is described. The synthesis highlights hydrozirconation, transmetalation, aldehyde addition sequence to install E-trisubstituted olefin and C7 stereocenter, and the first use of an intramolecular Buchwald-like amidation reaction to close the 19-membered macrolactam. Copyright

Expeditious syntheses of sugar-modified nucleosides and collections thereof exploiting furan-, pyrrole-, and thiophene-based siloxy dienes

A series of individual sugar-modified pyrimidine nucleosides including enantiomerically enriched 2',3'-dideoxynucleosides 14a-c (α and β anomers of L- and D-series), 2',3'-dideoxy-4'-thionucleosides 21a-c (α and β anomers of L- and D-series), and 2',3'-dideoxy-4'-azanucleosides 28a-c (β anomers of L- and D-series) were synthesized, with uniform chemistry and high stereochemical efficiency, exploiting a triad of versatile heterocyclic siloxy dienes, namely, 2-(tert-butyldimethylsiloxy)furan (TBSOF), 2-(tert- butyldimethylsiloxy)thiophene (TBSOT), and N-(tert-butoxycarbonyl)-2-(tert- butyldimethylsiloxy)pyrrole (TBSOP). The synthetic procedure advantageously used both enantiomers of glyceraldehyde acetonide (D-1 and L-1) as sources of chirality and as synthetic equivalents of the formyl cation. The outlined chemistry also allowed for the rapid assemblage of a 30-member collection of racemic nucleosides (D,L-L) as well as one 15-member ensemble of chiral analogues (L-L), along with some related sublibraries.