3‐Chloro‐3‐(diphenylmethoxy)‐1,1,1,5,5,5‐hexamethyltrisiloxane

[309963-45-9] C19H29ClO3Si3 (MW 425.14) InChI = 1S/C19H29ClO3Si3/c1-24(2,3)22-26(20,23-25(4,5)6)21-19(17-13-9-7-10-14-17)18-15-11-8-12-16-18/h7-16,19H,1-6H3 InChIKey = MXYRUZAVJVIZOX-UHFFFAOYSA-N (reagent used as a 5′-silyl protecting group for ribonucleoside phosphoramidite synthesis)1 Alternative Names:  benzhydryloxybis(trimethylsiloxy)chlorosilane, BzH-Cl. Physical Data: mp 0.25 °C; bp 135–140 °C; d 1.0345 g cm−3. Solubility: most organic solvents (tetrahydrofuran, dimethylformamide, dichloromethane). Form Supplied in: liquid; commercially available from Gelest. Preparation: the reagent is produced through the reaction between diphenylmethanol and bis(trimethylsiloxy)dichlorosilane.1 A related silyl chloride, bis(trimethylsiloxy)cyclododecyloxysilyl chloride (DODCl), is produced using analogous methods, by the reaction of cyclododecanol with bis(trimethylsiloxy)dichlorosilane. Handling, Storage, and Precautions: handling and precautions are unknown. Should be stored in a cool (< 5 °C) and anhydrous environment.

[1]  J. Watts,et al.  Chemically modified siRNA: tools and applications. , 2008, Drug discovery today.

[2]  S. K. Mahto,et al.  Combined Approaches to Site-Specific Modification of RNA. , 2008, ACS chemical biology.

[3]  R. Micura,et al.  2′-Methylseleno-modified oligoribonucleotides for X-ray crystallography synthesized by the ACE RNA solid-phase approach , 2007, Nucleic acids research.

[4]  J. Wachtveitl,et al.  RNA as scaffold for pyrene excited complexes. , 2008, Bioorganic & medicinal chemistry.

[5]  G. Stock,et al.  Base-specific spin-labeling of RNA for structure determination , 2007, Nucleic acids research.

[6]  J. Engels,et al.  Spin labeling of oligonucleotides with the nitroxide TPA and use of PELDOR, a pulse EPR method, to measure intramolecular distances , 2007, Nature Protocols.

[7]  Hongbin Yan,et al.  Synthesis of 3’,5’-cyclic diguanylic acid (cdiGMP) Using 1-(4-chlorophenyl)-4-ethoxypiperidin-4-yl as a Protecting Group for 2’-hydroxy Functions of Ribonucleosides , 2007, Nucleosides, nucleotides & nucleic acids.

[8]  Chuanzheng Zhou,et al.  2-(4-Tolylsulfonyl)ethoxymethyl (TEM)-a new 2'-OH protecting group for solid-supported RNA synthesis. , 2007, Organic & biomolecular chemistry.

[9]  S. Crooke,et al.  Human RNase H1 Discriminates between Subtle Variations in the Structure of the Heteroduplex Substrate , 2007, Molecular Pharmacology.

[10]  M. Caruthers,et al.  Synthesis of mixed sequence borane phosphonate DNA. , 2006, Journal of the American Chemical Society.

[11]  K. Alexander,et al.  High potency silencing by single-stranded boranophosphate siRNA , 2006, Nucleic acids research.

[12]  M. Germann,et al.  Synthesis of a 2'-Se-uridine phosphoramidite and its incorporation into oligonucleotides for structural study. , 2005, Organic letters.

[13]  K. Misra,et al.  One-Pot Synthesis of TBMPS (bis [tert-Butyl)-1 Pyrenylmethyl-Silyl) Chloride as a Novel Fluorescent Silicon-Based Protecting Group for Protection of 5′-OH Nucleosides and Its Use as Purification Handle in Oligonucleotide Synthesis , 2005, Nucleosides, Nucleotides & Nucleic Acids.

[14]  R. Pon,et al.  LARGE-SCALE SYNTHESIS OF “Cpep” RNA MONOMERS AND THEIR APPLICATION IN AUTOMATED RNA SYNTHESIS , 2005, Nucleosides, nucleotides & nucleic acids.

[15]  S. Müller,et al.  Current Strategies for the Synthesis of RNA , 2004 .

[16]  R. Kaiser,et al.  Recent advances in the high-speed solid phase synthesis of RNA. , 2004, Current opinion in chemical biology.

[17]  S. Scaringe,et al.  Synthesis of helix 69 of Escherichia coli 23S rRNA containing its natural modified nucleosides, m3ψ and ψ , 2002 .

[18]  S. Scaringe,et al.  Synthesis of a 3-methyluridine phosphoramidite to investigate the role of methylation in a ribosomal RNA hairpin. , 2002, Bioorganic & medicinal chemistry.

[19]  S. Scaringe,et al.  RNA oligonucleotide synthesis via 5'-silyl-2'-orthoester chemistry. , 2001, Methods.

[20]  S. Scaringe Advanced 5'-silyl-2'-orthoester approach to RNA oligonucleotide synthesis. , 2000, Methods in enzymology.

[21]  M. Caruthers,et al.  Novel RNA Synthesis Method Using 5‘-O-Silyl-2‘-O-orthoester Protecting Groups , 1998 .

[22]  C. Reese,et al.  Use of the 1-(2-fluorophenyl)-4-methoxypiperidin-4-yl (Fpmp) and related protecting groups in oligoribonucleotide synthesis: stability of internucleotide linkages to aqueous acid. , 1994, Nucleic acids research.