214468-42-5

Basic information

• Product Name: p-methylphenyl 6-O-tert-butyldiphenylsilyl-1-thio-β-D-glucopyranoside
• Synonyms: p-methylphenyl 6-O-tert-butyldiphenylsilyl-1-thio-β-D-glucopyranoside
• CAS NO: 214468-42-5
• Molecular Weight: 524.753
• Mol File: 214468-42-5.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: p-methylphenyl 6-O-tert-butyldiphenylsilyl-1-thio-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: p-methylphenyl 6-O-tert-butyldiphenylsilyl-1-thio-β-D-glucopyranoside(214468-42-5)
• EPA Substance Registry System: p-methylphenyl 6-O-tert-butyldiphenylsilyl-1-thio-β-D-glucopyranoside(214468-42-5)

Safety Data

• Hazardous Substances Data: 214468-42-5(Hazardous Substances Data)

Upstream product

• 604-69-3 β-D-glucose pentaacetate 
• 28244-94-2 p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 106-45-6 para-thiocresol 
• 83-87-4 D-glucose pentaacetate 
• 1152-39-2 p-methylphenyl 1-thio-β-D-glucopyranoside 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Downstream Products

• 596087-16-0 C₅₃H₅₄O₈SSi 
• 807361-70-2 p-tolyl 2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-1-thio-α-D-glucopyranoside 
• 807360-79-8 p-methylphenyl 2,3,4-tri-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-1-thio-β-D-glucopyranoside 
• 1582775-47-0 methyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranosyl-(1→4)-2-azido-2-deoxy-3-O-benzyl-6-O-benzyl-α-D-glucopyranoside 
• 1582775-49-2 methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyl-(1→4)-2-azido-2-deoxy-3-O-benzyl-6-O-benzyl-α-D-glucopyranoside 
• 1582775-53-8 methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate-(1→4)-2-azido-2-deoxy-3-O-benzyl-6-O-benzyl-α-D-glucopyranoside 
• 1582775-54-9 methyl β-D-glucopyranosyluronate-(1→4)-2-azido-2-deoxy-3-O-benzyl-6-O-benzyl-α-D-glucopyranoside 
• 1582775-63-0 C₃₀H₄₂F₁₀N₂O₁₈ 
• 1582775-66-3 C₃₆H₅₀F₁₀N₂O₂₄ 
• 1582775-68-5 C₄₄H₆₀F₁₃N₃O₂₉ 

Relevant articles and documents

An Efficient Modular One-Pot Synthesis of Heparin-Based Anticoagulant Idraparinux

Idraparinux is a fully O-sulfated α-methyl glycoside of heparin pentasaccharide motif known to interact with the antithrombin III domain and act as anticoagulant. The current most effective synthesis of Idraparinux is complicated and nonstereoselective, requiring numerous stepwise procedures with low yields. We report here an efficient modular one-pot synthesis of Idraparinux involving the use of a glycosyl phosphate with 6-O-tert-butyl diphenyl silyl group and a d-glucuronic acid-containing disaccharide thioglycoside with 6-O-acetyl group as donor building blocks for the α-directing one-pot glycosylations with an l-iduronic acid-containing disaccharide acceptor building block. The uronic acid was incorporated in a disaccharide module used in the one-pot synthesis to avoid the complicated late-stage installation of these acidic sugars. The one-pot synthesis of Idraparinux demonstrated here is an effective strategy and should be applicable to the modular assembly of other heparan sulfates with regiodefined sulfation pattern for functional study.

Fluorous-assisted chemoenzymatic synthesis of heparan sulfate oligosaccharides

The chemoenzymatic synthesis of heparan sulfate tetrasaccharide (1) and hexasaccharide (2) with a fluorous tag attached at the reducing end is reported. The fluorous tert-butyl dicarbonate (FBoc) tag did not interfere with enzymatic recognition

Concise synthesis of two trisaccharides related to the saponin isolated from Centratherum anthelminticum

Chemical synthesis of two trisaccharides related to the saponin isolated from Centratherum anthelminticum is reported. Stereoselective, high-yielding glycosylation strategies were developed using H2SO4 immobilized on silica for activ