10303-88-5Relevant articles and documents
AMINO-ACIDS AS CHIRAL SYNTHONS : SYNTHESIS OF ENANTIOMERICALLY PURE α-HYDROXY ESTERS.
Larcheveque, Marc,Petit, Yves
, p. 3705 - 3706 (1984)
Reaction of lithium homocuprates with α-hydroxy β-bromo ester derivated from aspartic acid affords α-hydroxy esters of high enantiomerical purity.
Determination of the absolute configuration of the glycerol component in poly(glycosylglycerolphosphates) by GLC-MS
Beynon,Richards
, p. 263 - 268 (1994)
Assignment of the stereochemistry of the glycerol residue in poly(glycosyl-glycerol phosphates) may be achieved by release of the chiral glycerol component, followed by its conversion to an appropriate derivative, and assignment of absolute stereochemistry by comparison with standards of known chirality.
d- and l-Serine, useful synthons for the synthesis of 24-hydroxyvitamin D3 metabolites. A formal synthesis of 1α,24R,25-(OH)3-D3, 24R,25-(OH)2-D3 and 24S,25-(OH)2-D3
Fernandez, Carlos,Gándara, Zoila,Gómez, Generosa,Covelo, Berta,Fall, Yagamare
, p. 2939 - 2942 (2007)
d- and l-Serine have been used for the enantioselective synthesis of tosylates 7a and 7b, useful building blocks for the synthesis of triols 5a and 5b which have already been obtained via a diastereoselective synthesis and used for the synthesis of 2a, 2b and 2c. We have thus performed a formal synthesis of 24S,25-(OH)2-D3, 24R,25-(OH)2-D3 and 1α,24R,25-(OH)3-D3.
3-(Alkylthio)-1,2-bis(siloxy)-3-butenes as efficient chirality transferred building blocks
Masuya, Keiichi,Tanino, Keiji,Kuwajima, Isao
, p. 7965 - 7968 (1994)
In the presence of Me2AlCl, reactions of the title compounds with a variety of aldehydes proceeded with high efficacy of chirality transfer to give the corresponding optically pure ene adducts, which could be converted to the γ-lactones, e.g.,
A NEW APPROACH TO THE SYNTHESIS OF ETHER PHOSPHOLIPIDS. PREPARATION OF 1,2-DIALKYLGLYCEROPHOSPHORYLCHOLINES FROM L-GLYCERIC ACID
Bhatia, Suresh K.,Hajdu, Joseph
, p. 271 - 274 (1987)
A novel stereospecific synthesis of antitumor active ether phospholipids is reported.
Synthesis and biological evaluation of enantiomerically pure glyceric acid derivatives as LpxC inhibitors
Tangherlini, Giovanni,Torregrossa, Tullio,Agoglitta, Oriana,K?hler, Jens,Melesina, Jelena,Sippl, Wolfgang,Holl, Ralph
, p. 1032 - 1044 (2016/02/19)
Inhibitors of the UDP-3-O-[(R)-3-hydroxymyristoyl]-N-acetylglucosamine deacetylase (LpxC) represent a promising class of novel antibiotics, selectively combating Gram-negative bacteria. In order to elucidate the impact of the hydroxymethyl groups of diol (S,S)-4 on the inhibitory activity against LpxC, glyceric acid ethers (R)-7a, (S)-7a, (R)-7b, and (S)-7b, lacking the hydroxymethyl group in benzylic position, were synthesized. The compounds were obtained in enantiomerically pure form by a chiral pool synthesis and a lipase-catalyzed enantioselective desymmetrization, respectively. The enantiomeric hydroxamic acids (R)-7b (Ki = 230 nM) and (S)-7b (Ki = 390 nM) show promising enzyme inhibition. However, their inhibitory activities do not substantially differ from each other leading to a low eudismic ratio. Generally, the synthesized glyceric acid derivatives 7 show antibacterial activities against two Escherichia coli strains exceeding the ones of their respective regioisomes 6.
Total synthesis of (-)-isoamericanin A and (+)-isoamericanol A
Pilkington, Lisa I.,Barker, David
, p. 1037 - 1046 (2014/03/21)
The enantioselective total synthesis of the biologically active 1,4-benzodioxane lignans isoamericanin A (2) and isoamericanol A (3) has been achieved in 11 and 12 steps, respectively. These benzodioxane lignan natural products, and others that contain 9-hydroxymethyl group, show a wide range of biological properties. The 1,4-benzodioxane ring was formed by an acid-catalysed cyclisation, which gave the desired trans isomer exclusively. This method will allow the synthesis of a number of benzodioxane compounds containing a 9-hydroxymethyl group The total syntheses of (-)-isoamericanin A and (+)-isoamericanol A are described. The key steps were a Mitsunobu etherification and the acid-catalysed formation of the 1,4-benzodioxane moiety with exclusive formation of the desired trans isomer. Copyright
