168253-07-4

Basic information

• Product Name: 2-C-(2,3,4,6-Tetra-O-benzyl-b-D-glucopyranosyl) ethyne
• Synonyms: 2-C-(2,3,4,6-Tetra-O-benzyl-b-D-glucopyranosyl) ethyne;3,7-Anhydro-1,2-dideoxy-4,5,6,8-tetrakis-O-(phenylmethyl)-D-glycero-D-gulo-oct-1-ynitol
• CAS NO: 168253-07-4
• Molecular Formula: C₃₆H₃₆O₅
• Molecular Weight: 548.66804
• Mol File: 168253-07-4.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-C-(2,3,4,6-Tetra-O-benzyl-b-D-glucopyranosyl) ethyne(CAS DataBase Reference)
• NIST Chemistry Reference: 2-C-(2,3,4,6-Tetra-O-benzyl-b-D-glucopyranosyl) ethyne(168253-07-4)
• EPA Substance Registry System: 2-C-(2,3,4,6-Tetra-O-benzyl-b-D-glucopyranosyl) ethyne(168253-07-4)

Safety Data

• Hazardous Substances Data: 168253-07-4(Hazardous Substances Data)

Upstream product

• 6207-45-0 2-(allyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 168336-52-5 C₃₉H₄₄O₆Si 
• 59531-24-7 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 
• 141196-28-3 trimethyl(((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)ethynyl)silane 

Downstream Products

• 287962-75-8 (R)-4-[(S)-1-Hydroxy-3-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-prop-2-ynyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 1355034-73-9 C₂₃H₂₇N₃O₉ 
• 1355034-75-1 C₂₄H₂₉N₃O₉ 
• 1355034-77-3 C₂₃H₂₆ClN₃O₉ 
• 1355034-79-5 C₂₄H₂₆F₃N₃O₉ 
• 1355034-83-1 C₂₃H₂₆FN₃O₉ 
• 1355034-85-3 C₂₄H₂₉N₃O₁₀ 
• 1355034-89-7 C₂₃H₂₆N₄O₁₁ 
• 1355034-91-1 C₂₄H₂₆N₄O₉ 
• 168105-48-4 C₇₂H₇₀O₁₀ 
• 1384643-88-2 C₄₃H₄₁NO₈ 
• 1384643-90-6 C₄₃H₄₃NO₆ 
• 1384643-91-7 C₄₃H₄₃NO₆ 
• 1384643-96-2 C₄₅H₄₄N₂O₆ 

Relevant articles and documents

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Total synthesis of indole-3-acetonitrile-4-methoxy-2-C-β-d- glucopyranoside. Proposal for structural revision of the natural product

Indole-3-acetonitrile-4-methoxy-2-C-β-d-glucopyranoside (1), a novel C-glycoside from Isatis indigotica with important cytotoxic activity, has been prepared in ten steps from ethynyl-β-C-glycoside 3 and 2-iodo-3-nitrophenyl acetate 6. Key steps in the synthesis include a Sonogashira coupling and a CuI-mediated indole formation. NMR spectroscopic data for synthetic 1 differs from that reported for the natural product. A revised structure for the natural product, containing an alternate carbohydrate substituent, is proposed. The Royal Society of Chemistry 2012.

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