52785-41-8Relevant articles and documents
Synthesis method of Fmoc-O-tert-butyl-L-threoninol
-
, (2017/07/12)
The present invention relates to a synthesis method of Fmoc-O-tert-butyl-L-threoninol, and mainly solves the technical problems that in a process of Fmoc-thr(tbu)-oh reduction by sodium borohydride, the reaction temperature is strictly required and a FMoc protecting group is decomposed, resulting in low yield and high cost. The synthesis method of the invention comprises the following steps: a. L-threonine reacts with thionyl chloride to form L-threonine methyl ester hydrochloride; b. the L-threonine methyl ester hydrochloride under the action of sodium hydroxide is reacted with benzyl chloroformate to produce z-thr-ome; c. the Z-thr-ome reacts with introduced isobutene in the presence of methylene chloride and concentrated sulfuric acid, and alkali adjustment treatment is carried out to obtain z-thr (tbu)-ome; d. in the presence of acetone and water, the Z-thr(tbu)-ome is saponified with added alkali to obtain z-thr(tbu)-oh; e. the Z-thr(tbu)-oh is reduced to z-thr(tbu)-ol by sodium borohydride in tetrahydrofuran; f. the z-thr(tbu)-ol is hydrogenated in methanol to obtain H-thr(tbu)-ol; and g. N-(9-fluorenylmethoxycarbonyloxy)succinimide is added to the H-thr(tbu)-ol to obtain the Fmoc-O-tert-butyl -L-threoninol.
Anthranilimide-based glycogen phosphorylase inhibitors for the treatment of Type 2 diabetes: 2. Optimization of serine and threonine ether amino acid residues
Sparks, Steven M.,Banker, Pierette,Bickett, David M.,Clancy, Daphne C.,Dickerson, Scott H.,Garrido, Dulce M.,Golden, Pamela L.,Peat, Andrew J.,Sheckler, Lauren R.,Tavares, Francis X.,Thomson, Stephen A.,Weiel, James E.
scheme or table, p. 981 - 985 (2009/08/15)
Optimization of the amino acid residue of a series of anthranilimide-based glycogen phosphorylase inhibitors is described leading to the identification of serine and threonine ether analogs. t-Butylthreonine analog 20 displayed potent in vitro inhibition of GPa, low potential for P450 inhibition, and excellent pharmacokinetic properties.
Design, synthesis, and biological activities of potent and selective somatostatin analogues incorporating novel peptoid residues
Tran, Thuy-Anh,Mattern, Ralph-Heiko,Afargan, Michel,Amitay, Oved,Ziv, Ofer,Morgan, Barry A.,Taylor, John E.,Hoyer, Daniel,Goodman, Murray
, p. 2679 - 2685 (2007/10/03)
We report the synthesis, bioactivity, and structure-activity relationship studies of compounds related to the Merck cyclic hexapeptide c[Pro6-Phe7-D-Trp8-Lys9-Thr10-Phe11], L-363,301 (the n