- Synthesis method of Fmoc-O-tert-butyl-L-threoninol
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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.
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- 1,2,4-OXADIAZOLE AND THIADIAZOLE COMPOUNDS AS IMMUNOMODULATORS
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The present invention relates to 1,2,4-oxadiazole compounds of formula (I) and their use to inhibit the programmed cell death (PD1) signaling pathway and/or for treatment of disorders by inhibiting an immunosuppressive signal induced by PD-1,PD-L1 or PD-L2.
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Page/Page column 86
(2016/09/26)
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- Anthranilimide-based glycogen phosphorylase inhibitors for the treatment of Type 2 diabetes: 2. Optimization of serine and threonine ether amino acid residues
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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.
- 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.
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scheme or table
p. 981 - 985
(2009/08/15)
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- Substituted 2-arylimino heterocycles and compositions containing them, for use as progesterone receptor binding agents
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This invention relates to 2-arylimino heterocycles, including 2-arylimino-1,3-thiazolidines, 2-arylimino-2,3,4,5-tetrahydro-1,3-thiazines, 2-arylimino-1,3-thiazolidin-4-ones, 2-arylimino-1,3-thiazolidin-5-ones, and 2-arylimino-1,3-oxazolidines, and their use in modulating progesterone receptor mediated processes, and pharmaceutical compositions for use in such therapies.
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Page column 40
(2010/02/05)
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- Design, synthesis, and biological activities of potent and selective somatostatin analogues incorporating novel peptoid residues
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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
- Tran, Thuy-Anh,Mattern, Ralph-Heiko,Afargan, Michel,Amitay, Oved,Ziv, Ofer,Morgan, Barry A.,Taylor, John E.,Hoyer, Daniel,Goodman, Murray
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p. 2679 - 2685
(2007/10/03)
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- Studies on 2-Aziridinecarboxylic Acid. VI. Synthesis of β-Alkoxy-α-Amino Acids via Ring-opening Reaction of Aziridine
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The reaction of aziridine derivatives having a urethane-type protecting group with several alcohols in the presence of boron trifluoride etherate afford the corresponding optically pure O-alkylserine and O-alkylthreonine derivatives via a ring-opening reaction of aziridine in good yield.
- Nakajima, Kiichiro,Neya, Masahiro,Yamada, Shinichi,Okawa, Kenji
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p. 3049 - 3050
(2007/10/02)
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