203301-81-9

Basic information

• Product Name: 2-Furanol, 5-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]tetrahydro-, acetate, (5R)-
• CAS NO: 203301-81-9
• Molecular Formula: C23H30O4Si
• Molecular Weight: 398.574
• Mol File: 203301-81-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-Furanol, 5-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]tetrahydro-, acetate, (5R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Furanol, 5-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]tetrahydro-, acetate, (5R)-(203301-81-9)
• EPA Substance Registry System: 2-Furanol, 5-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]tetrahydro-, acetate, (5R)-(203301-81-9)

Safety Data

• Hazardous Substances Data: 203301-81-9(Hazardous Substances Data)

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 108-24-7 acetic anhydride 
• 128075-94-5 (R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}dihydrofuran-2(3H)-one 
• 201472-30-2 (R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-ol 
• 52813-63-5 (5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone 

Downstream Products

• 874382-93-1 (1'S,4'R)-1-[5'-tert-butyldiphenylsilyl-2',3'-dideoxy-β-L-ribofuranosyl]-2-methyl-3-benzyloxy-4-pyridinone 
• 874382-95-3 (1'R,4'R)-1-[5'-tert-butyldiphenylsilyl-2',3'-dideoxy-α-L-ribofuranosyl]-2-methyl-3-benzyloxy-4-pyridinone 
• 139594-87-9 amphidinolide F 
• 147058-39-7 1-(2,3-dideoxy-beta-L-ribofuranosyl)-5-fluorocytosine 
• 874383-01-4 (1'R,4'R)-1-[2',3'-dideoxy-α-L-ribofuranosyl]-2-methyl-3-benzyloxy-4-pyridinone 
• 874382-99-7 (1'S,4'R)-1-[2',3'-dideoxy-β-L-ribofuranosyl]-2-methyl-3-benzyloxy-4-pyridinone 
• 654054-86-1 (1'S,4'R)-1-[2',3'-dideoxy-β-L-ribofuranosyl]-2-methyl-3-hydroxy-4-pyridinone 
• 203302-06-1 2-[5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester 
• 203302-08-3 2-[5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester 
• 203302-07-2 2-[5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Total Synthesis of the Marine Macrolide Amphidinolide F

A new and efficient convergent approach toward the synthesis of amphidinolide F is described through the assembly of three fragments. The two trans-tetrahydrofurans were built by a diastereoselective C-glycosylation with titanium enolate of bulky N-acetyloxazolidinethiones. The side chain was inserted by a Liebeskind-Srogl cross-coupling reaction. A sulfone condensation/desulfonylation sequence, a Stille cross-coupling, and a macrolactonization were applied to connect the fragments.

The Utility of Furan-, Pyrrole-, and Thiophene-Based 2-Silyloxy Dienes as Demonstrated by Modular Synthesis of Annonaceous Acetogenin Core Units and Their Pyrrolidine and Thiolane Analogues

We report a modular strategy for obtaining the core units of annonaceous acetogenins and their nitrogen and sulfur analogues, which generates great structural diversity. This synthesis is based on the application of a reiterative vinylogous addition protocol involving a unique triad of silyloxy diene modules, 2-[(tert-butyldimethylsilyl)oxy]furan (TBSOF), N-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]pyrrole (TBSOP), and 2-[(tert-butyldimethylsilyl)oxy]thiophene (TBSOT) and suitable heteroatom-stabilized carbenium ions. By combining TBSOF, TBSOP, and TBSOT nucleophilic synthons with certain tetrahydrofuran, pyrrolidine, and thiolane acceptors, the construction of varied, adjacently linked oligo-heterocyclic motifs related to the core segments of the annonaceous acetogenins is assured. At first, the reliability of the pivotal coupling maneuver was certified, by assembling a collection of 18 model constructs, covering all oxygen, nitrogen, and sulfur heteroatom combinations (i.e., compounds 7-9, 13-15, and 19-21). This uniformed protocol was then suited to forge advanced bis-tetrahydrofuran, bis-pyrrolidine, and bis-thiolane scaffolds encompassing the heterocyclic core portion of various binuclear annonaceous acetogenins and relatives. The utility of this synthesis was demonstrated by the preparation of a repertoire of eight isomeric bis-tetrahydrofuran units, 41-48, two bis-pyrrolidine units, 62 and 63, and four bis-thiolane units, 78-81.