381718-96-3

Upstream product

• 100-44-7 benzyl chloride 
• 70267-24-2 (R)-2-hydroxydecanoic acid 
• 85398-16-9 (R)-2-Hydroxydecansaeuremethylester 
• 917222-22-1 methyl (R)-2-[(tetrahydro-2H-pyran-2-yl)oxy]decanoate 
• 917221-93-3 (R)-2-[(tetrahydro-2H-pyran-2-yl)oxy]decane-1-ol 
• 13125-66-1 n-heptylmagnesium bromide 
• 14618-80-5 (R)-benzyl glycidol 

Downstream Products

• 444809-06-7 Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-((R)-1-benzyloxymethyl-nonyloxy)-tetrahydro-pyran-4-yl ester 
• 444809-04-5 Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-((R)-1-benzyloxymethyl-nonyloxy)-tetrahydro-pyran-4-yl ester 
• 444809-08-9 (2R,3R,4S,5R,6R)-2-((R)-1-Benzyloxymethyl-nonyloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 444809-10-3 (2R,3R,4S,5S,6R)-2-((R)-1-Benzyloxymethyl-nonyloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 

Relevant academic research and scientific papers

A Novel Class of Defensive Compounds in Harvestmen: Hydroxy-γ-Lactones from the Phalangiid Egaenus convexus

When threatened, the harvestman Egaenus convexus (Opiliones: Phalangiidae) ejects a secretion against offenders. The secretion originates from large prosomal scent glands and is mainly composed of two isomers of 4-hydroxy-5-octyl-4,5-dihydro-3H-furan-2-one (1), a β-hydroxy-γ-lactone. The compounds were characterized by GC-MS of their microreaction derivatives, HRMS, and NMR. After the synthesis of all four possible stereoisomers of 1, followed by their separation by chiral-phase GC, the absolute configurations of the lactones in the Egaenus secretion was found to be (4S,5R)-1 (90%) and (4S,5S)-1 (10%). Hydroxy-γ-lactones represent a new class of exocrine defense compounds in harvestmen.

Synthesis of new enantiopure proton-ionizable crown ethers containing a dialkylhydrogenphosphate moiety

Seven new enantiopure proton-ionizable crown ethers containing a dialkylhydrogenphosphate moiety were prepared starting from optically active dialkyl-substituted oligoethylene glycols and phosphorus oxychloride followed by mild hydrolysis of the resulting macrocyclic chlorophosphates. Pentaethylene glycols having primary hydroxyl groups gave good yields of 17-crown-6 type ethers. Pentaethylene glycols with secondary hydroxyl groups rendered about the same amount of 17-crown-6 ethers and open chain dihydrogenphosphates in low yields. Tetraethylene glycols are reluctant to undergo macrocyclization with phosphorus oxychloride, especially the ones which contain secondary hydroxyl groups.

Novel chiral glycerol analogues building blocks. Application to the synthesis of bioactive glycoglycerolipid analogues

Monoacylglycosylglycerols show anti-tumor promoting effects: in order to study the role of the ester function we have prepared by simple methods (R)-1-O-benzyl-1,2-decandiol, (R)-3-O-benzyl-1-O-hexyl-sn-glycerol, and (R)-1-O-benzyl-5-oxo-1,2-decandiol; these optically active compounds are building blocks for the synthesis of monohexanoylglycosylglycerol isosters.