71998-68-0Relevant academic research and scientific papers
Direct Synthesis of Free α-Amino Acids by Telescoping Three-Step Process from 1,2-Diols
Inada, Haruki,Shibuya, Masatoshi,Yamamoto, Yoshihiko
, p. 709 - 713 (2019/01/25)
A practical telescoping three-step process for the syntheses of α-amino acids from the corresponding 1,2-diols has been developed. This process enables the direct synthesis of free α-amino acids without any protection/deprotection step. This method was also effective for the preparation of a 15N-labeled α-amino acid. 1,2-Diols bearing α,β-unsaturated ester moieties afforded bicyclic α-amino acids through intramolecular [3 + 2] cycloadditions. A preliminary study suggests that the resultant α-amino acids are resolvable by aminoacylases with almost complete selectivity.
Synthesis of Novel C-Pivot Lariat 18-Crown-6 Ethers and Their Efficient Purification
Jana, Susovan,Suresh, Vallabh,Lepore, Salvatore D.
, p. 1977 - 1980 (2015/09/01)
The syntheses of various lariat ethers including several not previously reported and their efficient purification are presented. The synthesis route brings together reactions from a variety of previous works leading to a robust and generalized approach to these C-pivot lariats. The main steps are condensation of functionalized diols with pentaethylene glycol ditosylate in the presence of potassium as a templating cation. Purification of the final products was achieved without chromatography by extracting from an aqueous potassium hydroxide solution.
Synthesis of optically active heterocyclic compounds via deracemization of 1,2-diol monotosylate derivatives bearing a long aliphatic chain by a combination of enzymatic hydrolysis with Mitsunobu inversion
Matsumoto, Kazutsugu,Usuda, Kazumasa,Okabe, Hirokazu,Hashimoto, Manabu,Shimada, Yasutaka
, p. 108 - 115 (2013/04/23)
We have succeeded in accomplishing the deracemization of (±)-2-acetoxydecyl and (±)-acetoxy-6-benzyloxyhexyl tosylates, which have a long substituent, via an enzyme-mediated enantioselective hydrolysis with a Mitsunobu inversion using polymer-supported triphenylphosphine to afford the corresponding (S)-enantiomer. Enantiomerically pure (S)- and (R)-γ-dodecalactones, a fruit flavor, were synthesized from (S)-2-acetoxydecyl tosylate as the mutual starting material. The poisonous alkaloid (S)-coniine was also synthesized using enantiomerically pure allyl amine as the key intermediate derived from (S)-acetoxy-6-benzyloxyhexyl tosylate.
MW-assisted Er(OTf)3-catalyzed mild cleavage of isopropylidene acetals in Tricky substrates
Procopio, Antonio,Gaspari, Marco,Nardi, Monica,Oliverio, Manuela,Romeo, Roberto
, p. 1961 - 1964 (2008/09/19)
Erbium(III) trifluoromethane sulfonate is proposed as a very gentle Lewis acid catalyst in a MW-assisted chemoselective method for the cleavage of isopropylidene acetals in awkward substrates by using pure water as the solvent.
Synthesis and biological evaluation of several structural analogs of 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand
Suhara, Yoshitomo,Oka, Saori,Kittaka, Atsushi,Takayama, Hiroaki,Waku, Keizo,Sugiura, Takayuki
, p. 854 - 867 (2007/10/03)
2-Arachidonoylglycerol (2-AG (1)) is an endogenous ligand for the cannabinoid receptors (CB1 and CB2). There is growing evidence that 2-arachidonoylglycerol plays important physiological and pathophysiological roles in various mammalian tissues and cells,
Selective cleavage of acetals with ZnBr2 in dichloromethane
Ribes, Celia,Falomir, Eva,Murga, Juan
, p. 1239 - 1244 (2007/10/03)
A selective cleavage of acetals of 1,2- and 1,3-diols has been achieved under mild conditions using ZnBr2 in dichloromethane at room temperature. Acetal types cleavable by this procedure include benzylidene, isopropylidene and cyclohexylidene acetals. This method is compatible with several other types of hydroxyl protecting groups such as Bn, Bz, TBDPS, TIPS and TBDMS.
Efficient chemoselective deprotection of silyl ethers using catalytic 1-chloroethyl chloroformate in methanol
Yeom, Chang-Eun,Kim, Young Jong,Lee, So Young,Shin, Yong Je,Kim, B. Moon
, p. 12227 - 12237 (2007/10/03)
Fast and chemoselective desilylation of silyl-protected alcohols was achieved using a catalytic amount of 1-chloroethyl chloroformate in methanol. With a minimal amount of 1-chloroethyl chloroformate as the source for anhydrous HCl, extremely efficient cleavage of silyl ethers of primary and secondary alcohols was accomplished, and chemoselective deprotection of one silyl ether in the presence of another silyl or other acid-labile group was possible through controlling the amount of the chloroformate and reaction time.
Microencapsulation of osmium tetroxide in polyurea
Ley, Steven V.,Ramarao, Chandrashekar,Lee, Ai-Lan,stergaard, Niels,Smith, Stephen C.,Shirley, Ian M.
, p. 185 - 187 (2007/10/03)
(Matrix presented) Osmium tetroxide has been microencapsulated in a polyurea matrix using an in situ interfacial polymerization approach. These microcapsules have been effectively used as recoverable and reusable catalysts in the dihydroxylation of olefins.
Synthesis and biological activities of novel structural analogues of 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand
Suhara, Yoshitomo,Nakane, Shinji,Arai, Shunsuke,Takayama, Hiroaki,Waku, Keizo,Ishima, Yoshio,Sugiura, Takayuki
, p. 1985 - 1988 (2007/10/03)
Novel analogues of 2-arachidonoylglycerol (2-AG), an endogenous cannabinoid receptor ligand, were developed. Chemical synthesis of these analogues (2-AGA105 and 2-AGA109) was accomplished starting from 2-octyn-1-ol and diethyl malonate and employing Wittig coupling of triene phosphonate with an aldehyde intermediate in a convergent and stereoselective manner. These analogues should be useful lead compounds for the development of novel 2-AG mimetics.
Syntheses of spacer-armed carbohydrate model compounds
Kerekgyarto, Janos,Nagy, Zoltan,Szurmai, Zoltan
, p. 107 - 115 (2007/10/03)
Commercially available chemicals, such as diethylene glycol, 1,9-nonanediol, 9-decen-1-ol, 1,2,6-hexanetriol, and p-nitrophenol were used to prepare spacer-armed carbohydrate derivatives. Glycosides of D-glucose, N-acetyl-D-glucosamine and 3-O-methyl-D-glucose have been synthesized, carrying reactive groups at the end of the spacer-arms. These glycosides are capable of forming neoglycoproteins. When bromo sugars were reacted with highly apolar aglycones in the presence of mercuric cyanide or mercuric bromide, a considerable amount of '2-OH-compounds' (such as 9-hydroxynonyl 3,4,6-tri-O-acetyl-β-D-glucopyranoside) were formed. Some spacer-armed derivatives (such as 9,10-epoxydecyl β-D-glucopyranoside) are theoretically a mixture of diastereomers, but this fact does not mirror in the 1H and 13C NMR spectra.
