215313-29-4

Basic information

• Product Name: Dodecanoic acid (2S,3R,4S,5S,6R)-4,5-bis-dodecanoyloxy-6-dodecanoyloxymethyl-2-{2-[(S)-2-(1H-imidazol-4-yl)-1-methoxycarbonyl-ethylamino]-cyclohexylsulfanyl}-tetrahydro-pyran-3-yl ester
• CAS NO: 215313-29-4
• Molecular Weight: 1174.76
• Mol File: 215313-29-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Dodecanoic acid (2S,3R,4S,5S,6R)-4,5-bis-dodecanoyloxy-6-dodecanoyloxymethyl-2-{2-[(S)-2-(1H-imidazol-4-yl)-1-methoxycarbonyl-ethylamino]-cyclohexylsulfanyl}-tetrahydro-pyran-3-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Dodecanoic acid (2S,3R,4S,5S,6R)-4,5-bis-dodecanoyloxy-6-dodecanoyloxymethyl-2-{2-[(S)-2-(1H-imidazol-4-yl)-1-methoxycarbonyl-ethylamino]-cyclohexylsulfanyl}-tetrahydro-pyran-3-yl ester(215313-29-4)
• EPA Substance Registry System: Dodecanoic acid (2S,3R,4S,5S,6R)-4,5-bis-dodecanoyloxy-6-dodecanoyloxymethyl-2-{2-[(S)-2-(1H-imidazol-4-yl)-1-methoxycarbonyl-ethylamino]-cyclohexylsulfanyl}-tetrahydro-pyran-3-yl ester(215313-29-4)

Safety Data

• Hazardous Substances Data: 215313-29-4(Hazardous Substances Data)

Upstream product

• 4467-54-3 histidine methyl ester hydrochloride 
• 215312-94-0 cyclohexan-2-on-1-yl 2,3,4,6-tetra-O-lauroyl-1-thio-β-D-galactopyranoside 
• 112-16-3 n-dodecanoyl chloride 
• 10257-28-0 D-Galactose 
• 207907-62-8 1-S-acetyl-2,3,4,6-tetra-O-lauroyl-1-thio-β-D-galactopyranose 
• 207907-61-7 1,2,3,4,6-penta-O-lauroyl-α-D-galactopyranose 

Downstream Products

• 267232-92-8 (S)-3-(1H-Imidazol-4-yl)-2-[2-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylsulfanyl)-cyclohexylamino]-propionic acid methyl ester 

Relevant articles and documents

Solid-phase extraction on C18 silica as a purification strategy in the solution synthesis of a 1-Thio-β-D-galactopyranoside library

A novel strategy for the purification of carbohydrate-based chemical libraries synthesized in solution was developed. Purification of reaction products was accomplished by means of solid-phase extraction enabled by protecting the 2-, 3-, 4-, and 6-hydroxyl groups of a galactose derivative as their hydrophobic O-laurates. The presence of multiple O-laurates allowed adsorption of reaction products onto C18 silica while reagents and by-products were washed away with MeOH. Products were quantitatively eluted with pentane. Purification of products using solid-phase extraction offers the combined advantages of solution synthesis (normal solution reactivity and ease of reaction monitoring) with those of solid-phase synthesis (facile product isolation permitting the use of large excesses of reagents). To demonstrate the utility of the hydrophobic recovery-procedure, tetra-O-lauroyl-β-d-galactopyranose-1-thiol was subjected to high-yielding reactions with a panel of Michael-acceptors and an α-chloro ketone. The resulting ketone adducts were then either reduced to the alcohols or reductively aminated with a selection of amino acids to give 30 different 1-thio-β-d-galactosides as mixtures of four diastereomers after removal of protecting groups. At each step, the product was separated from the reagents and their by-products by simple adsorption onto C18 silica, washing with MeOH and elution of product with pentane. After completion of the combinatorial chemistry sequence, the O-laurates were cleaved by methanolysis and the product methyl laurate in turn removed from the desired water-soluble products by C18 adsorption. Individual library members were thus conveniently produced on 10-30mg scales at purity levels of >90%. One of the 1-thio-β-d-galactosides thus produced was found to be a competitive inhibitor of the β-galactosidase from E. coli with K(i) value of 1.7μM. Copyright (C) 1998 Elsevier Science Ltd.