1451369-72-4

Basic information

• Product Name: 4-methylphenyl 3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-1-thio-α-L-arabinofuranoside
• Synonyms: 4-methylphenyl 3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-1-thio-α-L-arabinofuranoside
• CAS NO: 1451369-72-4
• Molecular Weight: 498.831
• Mol File: 1451369-72-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4-methylphenyl 3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-1-thio-α-L-arabinofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methylphenyl 3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-1-thio-α-L-arabinofuranoside(1451369-72-4)
• EPA Substance Registry System: 4-methylphenyl 3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-1-thio-α-L-arabinofuranoside(1451369-72-4)

Safety Data

• Hazardous Substances Data: 1451369-72-4(Hazardous Substances Data)

Upstream product

• 69304-37-6 1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane 
• 527682-82-2 4'-methylphenyl 1-thio-α-L-arabinofuranoside 

Downstream Products

• 1451369-78-0 N-benzyloxycarbonyl-4R-[2,3,5-tri-O-acetyl-β-L-arabinofuranosyl]oxy-L-proline benzyl ester 
• 1451369-68-8 N-benzyloxycarbonyl-4R-[3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-L-arabinofuranosyl]oxy-L-proline benzyl ester 
• 1451369-67-7 C₅₅H₆₉NO₁₀SSi₂ 
• 1451369-96-2 C₅₂H₇₁NO₁₀SSi₂ 
• 1488357-76-1 C₅₃H₈₆O₁₁SSi₄ 
• 1451369-70-2 N-tertbutyloxycarbonyl-trans-4-O-(3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-L-arabinofuranosyl)oxy-L-proline benzyl ester 
• 1451369-66-6 4-methylphenyl 2-O-(2-naphthyl)methyl-3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-1-thio-α-L-arabinofuranoside 
• 1451369-76-8 C₈₉H₁₃₇NO₂₀SSi₆ 

Relevant articles and documents

Stereoselective synthesis of Arabidopsis CLAVATA3 (CLV3) glycopeptide, unique protein post-translational modifications of secreted peptide hormone in plant

The unique hydroxylproline (Hyp)-linked O-glycan modification is a common process in hydroxyproline-rich glycoproteins (HRGPs). The modification occurs through post-translational hydroxylation at 4-position of proline residues some of which are followed by O-glycosylation at the resulting Hyp which is also found in some secreted peptide hormones such as CLAVATA3 (CLV3) of Arabidopsis thaliana plants. An active mature CLV3 is a tridecapeptide linked to β-l-Araf-(1→2)-β-l-Araf-(1→2)-β-l-Araf at a Hyp residue in the center of the peptide sequence such as Arg-Thr-Val-Hyp-Ser-Gly-Hyp(l- Arafn)-Asp-Pro-Leu-His-His-His (n = 3). We report here the synthesis of the secreted and modified CLV3 glycopeptide with all glycoforms (Araf 0-3CLV3) of A. thaliana plants. A highly stereoselective β-arabinofuranosylation of Hyp derivatives as the key step of the synthesis of CLV3 glycopeptide was achieved by NAP ether-mediated IAD, which was effectively applied to the synthesis of oligoarabinosylated hydroxylproline [Hyp(l-Araf1-3)] derivatives. Fmoc-solid phase peptide synthesis was carried out using COMU as the coupling reagent for the introduction of [Hyp(l-Araf0-3)] derivatives as well as further elongation to the CLV3 glycopeptides.