127943-95-7

Basic information

• Product Name: methyl (1R,3R)-3-(tert-butyldimethylsilyloxy)cyclohex-4-ene-1-carboxylate
• Synonyms: methyl (1R,3R)-3-(tert-butyldimethylsilyloxy)cyclohex-4-ene-1-carboxylate
• CAS NO: 127943-95-7
• Molecular Weight: 270.444
• Mol File: 127943-95-7.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: methyl (1R,3R)-3-(tert-butyldimethylsilyloxy)cyclohex-4-ene-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (1R,3R)-3-(tert-butyldimethylsilyloxy)cyclohex-4-ene-1-carboxylate(127943-95-7)
• EPA Substance Registry System: methyl (1R,3R)-3-(tert-butyldimethylsilyloxy)cyclohex-4-ene-1-carboxylate(127943-95-7)

Safety Data

• Hazardous Substances Data: 127943-95-7(Hazardous Substances Data)

Upstream product

• 4720-83-6 6-oxabicyclo[3.2.1]oct-3-en-7-one 
• 76140-13-1 endo-4-iodo-6-oxabicyclo<3,2,1>octan-7-one 
• 4771-80-6 1,2,5,6-tetrahydrobenzoic acid 
• 935-79-5 cis-1,2,3,6-tetrahydrophthalic anhydride 
• 19914-76-2 (1S-cis)-6-Chlorcarbonyl-3-cyclohexen-1-carbonsaeure-methylester 
• 119719-61-8 (1R,4R,5R)-4-iodo-6-oxabicyclo[3.2.1]octane-7-one 
• 109667-78-9 N-(4-chloro-7-oxo-6-oxabicyclo[3.2.1]octan-3-yl)acetamide 
• 6493-77-2 (R)-(+)-methyl 3-cyclohexene-1-carboxylate 
• 4841-84-3 dimethyl cis-1,2,3,6-tetrahydrophthalate 
• 5709-98-8 (R)-cyclohex-3-enecarboxylic acid 
• 31139-02-3 (1R,6S)-6-methoxycarbonyl-3-cyclohexene-1-carboxylic acid 
• 54911-89-6 (1R,5R)-methyl-5-hydroxycyclohex-3-enecarboxylate 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 1026073-45-9 methyl (1R,3R,4R,5S)-3-(tert-butyldimethylsilyloxy)-4-hydroxy-5-methylcyclohexane-1-carboxylate 
• 1339943-40-6 C₅₆H₇₆O₁₈Si 
• 1339943-42-8 C₅₀H₆₂O₁₈ 
• 1026074-30-5 (1R,2R,4R,6S)-2-tert-butyldimethylsilyloxy-4-hydroxymethyl-6-methylcyclohexyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranoside 
• 1026074-32-7 (1R,2R,4R,6S)-2-tert-butyldimethylsilyloxy-4-chloromethyl-6-methylcyclohexyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranoside 
• 1026074-33-8 (1R,2R,4R,6S)-2-tert-butyldimethylsilyloxy-4,6-dimethylcyclohexyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranoside 
• 1026074-34-9 (1R,2R,4R,6S)-2-hydroxy-4,6-dimethylcyclohexyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranoside 
• 1026073-51-7 methyl (1R,3R,4R,5S)-4-O-(2,3,4-tris-O-benzyl-6-deoxy-α-L-galactopyranosyl)-3,4-dihydroxy-5-methylcyclohexane-1-carboxylate 
• 1374760-20-9 C₁₆H₃₀O₄Si 
• 1446004-02-9 C₆₈H₇₈F₃NO₁₆ 
• 1446003-98-0 C₃₉H₆₂N₄O₁₅S 
• 1609184-34-0 C₃₂H₅₃NO₁₅ 
• 1609184-35-1 C₄₀H₆₁NO₁₉ 
• 1609184-38-4 C₅₈H₉₇N₃O₁₇ 

Relevant articles and documents

METHODS AND COMPOSITIONS FOR TREATING AND/OR PREVENTING MUCOSITIS

Methods for treating and/or preventing mucositis comprising administering to a subject in need thereof an effective amount of at least one compound chosen from E-selectin antagonists, pharmaceutically acceptable salts of E-selectin antagonists, prodrugs of E- selectin antagonists, and pharmaceutically acceptable salts of prodrugs of E-selectin antagonists, and compositions comprising at least one of such compound.

E-SELECTIN ANTAGONIST COMPOUNDS, COMPOSITIONS, AND METHODS OF USE

Methods and compositions using E-selectin antagonists are provided for the treatment and prevention of diseases and disorders treatable by inhibiting binding of E-selectin to an E-selectin ligand. Described herein are E-selectin antagonists including, for example, glycomimetic compounds, antibodies, aptamers and peptides that are useful in methods for treatment of cancers, and treatment and prevention of metastasis, inhibiting infiltration of the cancer cells into bone marrow, reducing or inhibiting adhesion of the cancer cells to endothelial cells including cells in bone marrow, and inhibiting thrombus formation. These E-selection antagonists have the general formula (Ia) below.

Pre-organization of the core structure of E-selectin antagonists

A new class of N-acetyl-dglucosamine (GlcNAc) mimics for Eselectin antagonists was designed and synthesized. The mimic consists of a cyclohexane ring substituted with alkyl substituents adjacent to the linking position of the fucose moiety. Incorporation into E-selectin antagonists led to the test compounds 8 and the 2'-benzoylated analogues 21, which exhibit affinities in the low micromolar range. By using saturation transfer difference (STD)-NMR it could be shown that the increase in affinity does not result from an additional hydrophobic contact of the alkyl substituent with the target protein E-selectin, but rather from a steric effect stabilizing the antagonist in its bioactive conformation. The loss of affinity found for antagonists 10 and 35 containing a methyl substituent in a remote position (and therefore unable to support to the stabilization of the core) further supports this hypothesis. Finally, when a GlcNAc mimetic containing two methyl substituents (52 and 53) was used, in which one methyl was positioned adjacent to the fucose linking position and the other was in a remote position, the affinity was regained.