147963-64-2

Basic information

• Product Name: Butanoic acid, 3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, (3R)-
• CAS NO: 147963-64-2
• Molecular Formula: C20H26O3Si
• Molecular Weight: 342.51
• Mol File: 147963-64-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Butanoic acid, 3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, (3R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Butanoic acid, 3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, (3R)-(147963-64-2)
• EPA Substance Registry System: Butanoic acid, 3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-, (3R)-(147963-64-2)

Safety Data

• Hazardous Substances Data: 147963-64-2(Hazardous Substances Data)

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 178246-78-1 (R)-3-(tert-Butyldiphenylsilanyloxy)butyric acid methyl ester 

Downstream Products

• 178246-84-9 α-Benzyl-ω-[(tert-butyl)diphenylsilyloxy]octa[(R)-oxy(3-methyl-1-oxopropan-1,3-diyl)] 
• 178246-85-0 C₄₈H₆₈O₁₇Si 
• 178246-96-3 (R)-3-(tert-Butyl-diphenyl-silanyloxy)-butyric acid (R)-2-((R)-2-{(R)-2-[(R)-2-((R)-2-benzyloxycarbonyl-1-methyl-ethoxycarbonyl)-1-methyl-ethoxycarbonyl]-1-methyl-ethoxycarbonyl}-1-methyl-ethoxycarbonyl)-1-methyl-ethyl ester 
• 178246-97-4 (R)-3-(tert-Butyl-diphenyl-silanyloxy)-butyric acid (R)-2-((R)-2-{(R)-2-[(R)-2-((R)-2-carboxy-1-methyl-ethoxycarbonyl)-1-methyl-ethoxycarbonyl]-1-methyl-ethoxycarbonyl}-1-methyl-ethoxycarbonyl)-1-methyl-ethyl ester 
• 178246-82-7 (R)-3-(tert-Butyl-diphenyl-silanyloxy)-butyric acid (R)-2-[(R)-2-((R)-2-benzyloxycarbonyl-1-methyl-ethoxycarbonyl)-1-methyl-ethoxycarbonyl]-1-methyl-ethyl ester 
• 178246-83-8 (R)-3-(tert-Butyl-diphenyl-silanyloxy)-butyric acid (R)-2-[(R)-2-((R)-2-carboxy-1-methyl-ethoxycarbonyl)-1-methyl-ethoxycarbonyl]-1-methyl-ethyl ester 
• 178246-94-1 (R)-3-(tert-Butyl-diphenyl-silanyloxy)-butyric acid (R)-2-((R)-2-benzyloxycarbonyl-1-methyl-ethoxycarbonyl)-1-methyl-ethyl ester 
• 178246-95-2 (R)-3-(tert-Butyl-diphenyl-silanyloxy)-butyric acid (R)-2-((R)-2-carboxy-1-methyl-ethoxycarbonyl)-1-methyl-ethyl ester 
• 178246-79-2 α-benzyl-ω-[(tert-butyl)diphenylsilyloxy]bis[(R)-oxy(3-methyl)-1-oxopropane-1,3-diyl] 

Relevant articles and documents

Synthesis and properties of alternating copolymers of 3-hydroxybutyrate and lactate units with different stereocompositions

Alternating copolymers of (R)-3-hydroxybutyrate ((R)-3HB) and lactate (2-hydroxypropionate: 2HP) units were synthesized by polycondensation reaction of preprepared dimeric monomers, (R)-3HB-(R)-2HP and (R)-3HB-(S)-2HP, in the presence of condensation agent. On the basis of the NMR analyses, it was confirmed that the obtained copolymers had an alternating sequence of (R)-3HB and 2HP units. In contrast to random copolymers of (R)-3HB and 2HP units, the repeating sequence of alternately connected (R)-3HB and 2HP units formed crystalline region. The copolymer with alternating sequence of (R)-3HB and (S)-2HP units had a melting temperature at 83 °C. On the other hands, the melting temperature of copolymer of (R)-3HB and (R)-2HP units was quite higher than those of the corresponding homopolymers (around 180°C) and reached to 233 °C. When the alternating copolymers were prepared from a mixture of stereoisomeric dimers, both the melting temperature and crystallinity varied in the wide ranges depending on the composition of stereoisomeric dimers.

Synthesis and NMR analysis in solution of oligo(3-hydroxyalkanoic acid) derivatives with the side chains of alanine, valine, and leucine (β-depsides): Coming full circle from PHB to β-peptides to PHB

Oligomers of 3-hydroxyalkanoic acids that contain two, three, and six residues with and without O-terminal (tBu)Ph2Si and C-terminal PhCH2 protection have been synthesized in such a way that the side chains on the oligoester backbone were those of the proteinogenic amino acids Ala (Me), Val (CHMe2), and Leu (CH2CHMe2). The enantiomerically pure 3-hydroxyalkanoates were obtained by Noyori hydrogenation of the corresponding 3-oxo-alkanoates with [Ru((R)-binap)Cl2](binap=2,2′bis(diphenylphosphanyl)-1, 1′-binaphthalene)/H2 (Scheme 1), and the coupling was achieved under the conditions (pyridine/(COCl)2, CH2Cl2, -78°) previously employed for the synthesis of various oligo(3-hydroxybutanoic acids) (Schemes 2 and 3). The Cotton effects in the CD spectra of the new oligoesters provided no hints about chiral conformation (cf. a helix) in MeOH, MeCN, octan-1-ol, or CF3CH2OH solutions (Figs. 1 and 2). Detailed NMR investigations in CDCl3 solution (Figs. 3-6, and Tables 1-5) of the hexa(3-hydroxyalkanoic acid) with the side chains of Val (HC), Ala (HB), Leu (HH), Val, Ala, Leu (from O- to C-terminus; 3) gave, on the NMR time-scale, no evidence for the presence of any significant amount of a 21- or a 31-helical conformation, comparable to those identified in stretched fibers of poly[(R)-3-hydroxybutanoic acid], or in lamellar crystallites and in single crystals of linear and cyclic oligo[(R)-3-hydroxybutanoic acids], or in the corresponding β-peptide(s) (the oligo(3-aminoalkanoic acid) analogs; 1-3). Thus, the extremely high flexibility (averaged or 'random-coil' conformation) of the polyester chain (CO - O rotational barrier ca. 13 kcal/mol; no hydrogen bonding), as compared to polyamide chains (CO - NH barrier ca. 18 kcal/mol; hydrogen bonding) has been demonstrated once again. The possible importance of this structural flexibility, which goes along with amphiphilic properties, for the role of PHB in biology, in evolution, and in prebiotic chemistry is discussed. Structural similarities of natural potassium-channeling proteins and complexes of oligo(3-hydroxybutanoates) with Na+, K+, or Ba2+ are alluded to (Figs. 7-9).

Monodisperse linear and cyclic oligo[(R)-3-hydroxybutanoates] containing up to 128 monomeric units

Using benzyl ester/(tert-butyl)diphenylsilyl ether protection, (COCl)2/pyridine esterification conditions, and a fragment-coupling strategy (with H2/Pd-C debenzylation and HF-pyridine desilylation), linear oligomers of (R)-3-hydroxyb