185303-79-1

Basic information

• Product Name: tert-Butyl-((S)-5-methoxy-tetrahydro-furan-2-ylmethoxy)-dimethyl-silane
• Synonyms: tert-Butyl-((S)-5-methoxy-tetrahydro-furan-2-ylmethoxy)-dimethyl-silane
• CAS NO: 185303-79-1
• Molecular Weight: 246.422
• Mol File: 185303-79-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: tert-Butyl-((S)-5-methoxy-tetrahydro-furan-2-ylmethoxy)-dimethyl-silane(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyl-((S)-5-methoxy-tetrahydro-furan-2-ylmethoxy)-dimethyl-silane(185303-79-1)
• EPA Substance Registry System: tert-Butyl-((S)-5-methoxy-tetrahydro-furan-2-ylmethoxy)-dimethyl-silane(185303-79-1)

Safety Data

• Hazardous Substances Data: 185303-79-1(Hazardous Substances Data)

Upstream product

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

Downstream Products

• 121154-54-9 2',3'-dideoxy-α-D-uridine 
• 5983-09-5 2',3'-Dideoxyuridine 
• 3416-05-5 3'-Deoxythymidine 

Relevant articles and documents

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.