1026074-33-8

Basic information

• Product Name: (1R,2R,4R,6S)-2-tert-butyldimethylsilyloxy-4,6-dimethylcyclohexyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranoside
• Synonyms: (1R,2R,4R,6S)-2-tert-butyldimethylsilyloxy-4,6-dimethylcyclohexyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranoside
• CAS NO: 1026074-33-8
• Molecular Weight: 674.993
• Mol File: 1026074-33-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (1R,2R,4R,6S)-2-tert-butyldimethylsilyloxy-4,6-dimethylcyclohexyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R,4R,6S)-2-tert-butyldimethylsilyloxy-4,6-dimethylcyclohexyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranoside(1026074-33-8)
• EPA Substance Registry System: (1R,2R,4R,6S)-2-tert-butyldimethylsilyloxy-4,6-dimethylcyclohexyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranoside(1026074-33-8)

Safety Data

• Hazardous Substances Data: 1026074-33-8(Hazardous Substances Data)

Upstream product

• 169532-17-6 ethyl 2,3,4-tri-O-benzyl-1-thio-α/β-L-fucopyranoside 
• 935-79-5 cis-1,2,3,6-tetrahydrophthalic anhydride 
• 19914-76-2 (1S-cis)-6-Chlorcarbonyl-3-cyclohexen-1-carbonsaeure-methylester 
• 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 
• 54911-89-6 (1R,5R)-methyl-5-hydroxycyclohex-3-enecarboxylate 
• 5709-98-8 (R)-cyclohex-3-enecarboxylic acid 
• 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 
• 1026073-50-6 methyl (1R,3R,4R,5S)-4-O-(2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranosyl)-3-O-(tert-butyldimethylsilyl)-3,4-dihydroxy-5-methylcyclohexane-1-carboxylate 
• 1026073-45-9 methyl (1R,3R,4R,5S)-3-(tert-butyldimethylsilyloxy)-4-hydroxy-5-methylcyclohexane-1-carboxylate 
• 1026073-44-8 methyl (1R,3R,4R,5R)-3,4-epoxy-5-(tert-butyldimethylsilyloxy)cyclohexane-1-carboxylate 
• 127943-95-7 methyl (1R,3R)-3-(tert-butyldimethylsilyloxy)cyclohex-4-ene-1-carboxylate 
• 119719-61-8 (1R,4R,5R)-4-iodo-6-oxabicyclo[3.2.1]octane-7-one 

Downstream Products

• 1026074-34-9 (1R,2R,4R,6S)-2-hydroxy-4,6-dimethylcyclohexyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranoside 

Relevant articles and documents

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.

Glycomimetic replacements for hexoses and N-acetyl hexosamines

Compounds and methods are provided for obtaining oligosaccharide mimics. More specifically, compounds and methods are described wherein oligosaccharide mimics are obtained by incorporating or substituting in a cyclohexane derivative.