78553-51-2

Usage

Uses

Used in Pharmaceutical Industry:
CBZ-ALPHA-ALLYL-L-GLY is used as a building block for the synthesis of nonracemic silylated amino acids, which are important in the development of pharmaceutical compounds. These amino acids can be incorporated into drug molecules to enhance their properties, such as selectivity, potency, and stability.
Used in Organic Synthesis:
In the field of organic synthesis, CBZ-ALPHA-ALLYL-L-GLY is utilized as a key intermediate for the preparation of various organic compounds. Its unique structure allows for regioselective reactions, enabling chemists to control the position of functional groups in the final product. This feature is particularly useful in the synthesis of complex organic molecules with specific biological activities or desired properties.
Used in Regioselective Preparation:
CBZ-ALPHA-ALLYL-L-GLY is used as a starting material for the regioselective preparation of nonracemic silylated amino acids. This process allows for the controlled formation of specific isomers, which is crucial in the development of enantiomerically pure compounds with desired biological activities. The regioselective synthesis of these amino acids can lead to the discovery of new pharmaceutical agents with improved therapeutic profiles.

Upstream product

• 16338-48-0 L-allylglycine 
• 501-53-1 benzyl chloroformate 
• 26054-60-4 ((S)-2-Oxo-oxetan-3-yl)-carbamic acid benzyl ester 
• 3536-96-7 vinylmagnesium chloride 
• 50299-14-4 N-Acetyl-α-allylglycine 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 127862-74-2 2-Benzyloxycarbonylamino-pent-4-enoic acid 2,2,2-trifluoro-ethyl ester 

Downstream Products

• 60655-04-1 (S)-N-Cbz-aspartic acid semialdehyde 
• 78553-47-6 methyl (2S)-2-[N-(benzyloxycarbonyl)amino]pent-4-enoate 
• 78553-48-7 ethyl (2S)-2-(benzyloxycarbonylamino)-4-pentenoate 
• 110686-06-1 trans-2-(Benzyloxycarbonylamino)-5-brom-4-hydroxy-valerolacton 
• 110579-32-3 cis-1-Benzyloxycarbonylamino-4-hydroxy-5-bromvalerolacton 
• 78553-49-8 tert-butyl (S)-2-(benzyloxycarbonylamino)pent-4-enoate 
• 203919-87-3 (R)-2-tert-Butoxycarbonylamino-pent-4-enoic acid 2-((S)-2-benzyloxycarbonylamino-pent-4-enoyloxy)-ethyl ester 
• 875574-66-6 (S)-methyl 2-((S)-2-(benzyloxycarbonylamino)pent-4-enamido)-5-(1,3-dioxolan-2-yl)pentanoate 
• 941297-01-4 C₄₂H₅₉N₇O₁₀ 
• 549521-90-6 (S)-N-benzyloxycarbonylallylglycyl-L-proline 
• 549521-91-7 (S)-N-benzyloxycarbonylallylglycyl-L-prolyl-L-γ-(R)-allylglutamic acid dibenzyl ester 
• 1844-40-2 (2S,4R)-4-hydroxypiperidine-2-carboxylic acid 
• 254882-06-9 (2S,4R)-methyl 1-(tert-butoxycarbonyl)-4-hydroxypiperidine-2-carboxylate 
• 403503-37-7 (2S,4R)-1-benzyl 2-methyl 4-hydroxypiperidine-1,2-dicarboxylate 

Relevant academic research and scientific papers

MACROCYCLIC COMPOUNDS FOR THE TREATMENT OF MEDICAL DISORDERS

Compounds, methods of use, and processes for making inhibitors of complement factor D or a pharmaceutically acceptable salt or composition thereof are provided. The inhibitors described herein target factor D and inhibit or regulate the complement cascade. The inhibitors of factor D described herein reduce excessive activation of complement.

Photoinduced Olefin Diamination with Alkylamines

Vicinal diamines are ubiquitous materials in organic and medicinal chemistry. The direct coupling of olefins and amines would be an ideal approach to construct these motifs. However, alkene diamination remains a long-standing challenge in organic synthesis, especially when using two different amine components. We report a general strategy for the direct and selective assembly of vicinal 1,2-diamines using readily available olefin and amine building blocks. This mild and straightforward approach involves in situ formation and photoinduced activation of N-chloroamines to give aminium radicals that enable efficient alkene aminochlorination. Owing to the ambiphilic nature of the β-chloroamines produced, conversion into tetra-alkyl aziridinium ions was possible, thus enabling diamination by regioselective ring-opening with primary or secondary amines. This strategy streamlines the preparation of vicinal diamines from multistep sequences to a single chemical transformation.

Divergent Access to Histone Deacetylase Inhibitory Cyclopeptides via a Late-Stage Cyclopropane Ring Cleavage Strategy. Short Synthesis of Chlamydocin

A unified step-economical strategy for accessing histone deacetylase inhibitory peptides is proposed, based on the late-stage installation of multiple zinc-binding functionalities via the cleavage of the strained cyclopropane ring in the common pluripoten

Conformation-constrained entirely-synthetic macrocyclic compounds

The invention relates to conformation-constrained entirely-synthetic macrocyclic compounds. A conformation-constrained, space-defined 12-30-member macrocyclic system (I) which is as shown in the description comprises three different constitution units: an aromatic template a, a confor1ation regulator b and a spaced part c, which are illustrated in the description and the claims. The macrocyclic compounds (I) can be easily prepared according to a parallel synthesis method or a combinatorial chemistry method, and are designed for realizing interaction with a specific biological target. Particularly, the compounds show agonistic or antagonistic activity to the following matters: a motilin receptor (MR), a 5-hydroxytryptamine receptor (5-HT2B receptor) of a subtype 5-HT2B, and a prostaglandin F2alpha receptor (FP receptor). Thus, the compounds are effectively used for treating gastrointestinal tract hypomotility disorder such as diabetic gastroparesis and constipation-predominant irritable bowel syndrome, CNS-related diseases such as migraine, schizophrenia, psychosis and depression, ocular hypertension such as glaucoma-related ocular hypertension, and premature delivery.

CONFORMATIONALLY CONSTRAINED, SYNTHETIC MACROCYCLIC COMPOUNDS

PROBLEM TO BE SOLVED: To provide a novel macrocyclic compound showing agonistic or antagonistic activity on a motilin receptor, a serotonin receptor and a prostaglandin F2A receptor. SOLUTION: This invention provides a macrocyclic compound incorporating building blocks A, B and C, represented by formula (I). The compound is useful for the treatment of motility disorders of the gastrointestinal tract, CNS-related disease and ocular hypertension. COPYRIGHT: (C)2015,JPO&INPIT

Diastereoselective synthesis of cyclic β2,3-amino acids utilizing 4-substituted-1,3-oxazinan-6-ones

The 4-substituted-1,3-oxazinan-6-one scaffold is a versatile synthon enabling access to a diverse array of β-amino acid derivatives. In this study, the synthetic utility of the 1,3-oxazinan-6-one is expanded to include the diastereoselective synthesis of

CONFORMATIONALLY CONSTRAINED, FULLY SYNTHETIC MACROCYCLIC COMPOUNDS

Conformationally restricted, spatially defined 12-30 membered macrocyclic ring systems of formulae Ia and Ib are constituted by three distinct molecular parts: Template A, conformation Modulator B and Bridge C. These macrocycles Ia and Ib are readily manufactured by parallel synthesis or combinatorial chemistry in solution or on solid phase. They are designed to interact with a variety of specific biological target classes, examples being the agonistic or antagonistic activity on G-protein coupled receptors (GPCRs), ion channels and signal transduction pathways. In particular, these macrocycles act as antagonists of the motilin receptor, the FP receptor and the purinergic receptors P2Y1, as modulators of the serotonin receptor of subtype 5-HT2B, as blockers of the voltage-gated potassium channel Kv1.3 and as inhibitors of the β-catenin-dependent “canonical” Wnt pathway. Thus they are showing great potential as medicaments for a variety of diseases.

CONFORMATIONALLY CONSTRAINED, FULLY SYNTHETIC MACROCYCLIC COMPOUNDS

Conformationally restricted, spatially defined 12-30 membered macrocyclic ring systems of type (I) are constituted by three distinct building blocks: an aromatic template a, a conformation modulator b and a spacer moiety c as detailed in the description and the claims. Macrocycles of type (I) are readily manufactured by parallel synthesis or combinatorial chemistry. They are designed to interact with specific biological targets. In particular, they show agonistic or antagonistic activity on the motilin receptor (MR receptor), on the serotonin receptor of subtype 5-HT2B (5-HT2B receptor), and on the prostaglandin F2 ? receptor (FP receptor). They are thus potentially useful for the treatment of hypomotility disorders of the gastrointestinal tract such as diabetic gastroparesis and constipation type irritable bowl syndrome; of CNS related diseases like migraine, schizophrenia, psychosis or depression; of ocular hypertension such as associated with glaucoma and preterm labour.

Straightforward synthesis of chiral silylated amino acids through hydrosilylation

A method using hydrosilylation of unsaturated amino acids was developed and optimised to obtain silylated amino acids. The platinum (Bu4N) 2PtCl6 complex was identified as the best catalyst, and the procedure tolerated dif

Asymmetric eschenmoser-claisen rearrangement for anti-β-substituted γ,δ-unsaturated amino acids

Optically active anti-β-substituted γ,δ-unsaturated amino acids are important synthetic building blocks in organic synthesis and for peptidomimetics. A novel asymmetric Eschenmoser-Claisen rearrangement with use of a C2-symmetric chiral auxiliary was developed to generate this type of amino acid. Excellent diastereoselectivities and high enantioselectivities (87-93% ee) were obtained after the chiral auxiliary was removed via iodolactonization/zinc reduction.