59768-71-7

Upstream product

• 98398-64-2 Adamantan-1-yl-iodo-acetyl chloride 
• 1373751-77-9 D-(adamant-1-yl)glycyl-L-alanyl-D-isoglutamine 
• 328969-77-3 (S)-N-(benzyloxycarbonyl)-2-(1-adamantyl)-2-aminoethanol 
• 895167-07-4 adamantan-1-yl-[2-tert-butoxycarbonylamino-3-(4-tert-butoxycarbonyloxy-phenyl)-propionylamino]-acetic acid 
• 895166-80-0 (R)-Adamantan-1-yl-[(S)-2-amino-3-(4-hydroxy-phenyl)-propionylamino]-acetic acid 
• 102572-74-7 R-methyl ester of amino-(1-adamantanyl)acetic acid 
• 2094-72-6 1-Adamantanecarbonyl chloride 
• 16091-97-7 1-adamantyl-2-hydroxyiminoacetic acid 
• 828-51-3 1-Adamantanecarboxylic acid 
• 16091-98-8 oxo-tricyclo[3.3.1.1^3,7]decan-1-yl-acetic acid 
• 1660-04-4 1-acetyladamantane 
• 98398-65-3 2-bromoadamantaneacetyl chloride 
• 82650-30-4 adamantan-1-yliodoacetic acid 
• 59768-70-6 2-(1-adamantyl)-2-bromoacetic acid 

Downstream Products

• 709031-29-8 3-hydroxy-1-adamantyl-glycine 
• 361442-00-4 (αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.1^3,7]decane-1-acetic acid 
• 328969-74-0 rac-N-(benzyloxycarbonyl)-2-(1-adamantyl)-2-aminoethanol 

Relevant academic research and scientific papers

A convenient method for the synthesis of (S)-N-boc-3- hydroxyadamantylglycine: A key intermediate of saxagliptin

(S)-N-Boc-3-Hydroxyadamantylglycine is a key intermediate of saxagliptin. It was synthesized from 1- adamantanecarboxylic acid to afford 1-acetyladamantane (2), which was converted into 2-(1-adamantyl)-2-oxoacetic acid (3) through oxidation, and then into 1-adamantyl-2-hydroxyimino acetic acid (4) followed by treatment of hydroxylamine hydrochloride, then 4 was reducted and Boc-protected to give N-Boc-adamantylglycine (5), which was oxidized with KMnO4 and treated with a chiral base. Utilizing this route, (S)-N-Boc-3- Hydroxyadamantylglycine was prepared. This work is to elaborate a convenient route to synthesize (S)-N-Boc-3-Hydroxyadamantylglycine and provide a new idea for the synthesis of saxagliptin.

Synthesis and immunostimulating properties of novel adamant-1-yl tripeptides

The aim of this work was to prepare L- and D-(adamant-1-yl)-Gly-L-Ala-D- isoGln peptides in order to study their adjuvant (immunostimulating) activities. Adjuvant activity of adamant-1-yl tripeptides was tested in the mouse model using ovalbumin as an ant

PROCESS FOR THE REDUCTIVE AMINATION OF α-KETO CARBOXYLIC ACIDS

The invention refers to a process for the reductive amination of α-keto carboxylic acids catalyzed by transition metal containing compounds.

Tumor-cell-targeted methionine-enkephalin analogues containing unnatural amino acids: Design, synthesis, and in vitro antitumor activity

A series of new peptides (8-25) containing different unnatural amino acids of the adamantane type (1-6), was synthesized. Possible cytotoxic activity on human cervical adenocarcinoma (HeLa), larynx carcinoma (HEp-2), colon carcinomas (HT-29, Caco-2), poorly differentiated cells from lymph node metastasis of colon carcinoma (SW-620), mammary gland adenocarcinoma (MCF-7), and melanoma (HBL) cells were tested by the MTT assay. The results were compared with the effect of methionine-enkephalin (Tyr-Gly-Gly-Phe-Met, or opioid growth factor, OGF), and its shorter N-terminal fragments. Peptide analogues containing Cαα-dialkylated glycine (Aaa1, 1) or Cα-alkylated glycine (Aaa2, 2) amino acid residues showed antitumor activity against melanoma, larynx carcinoma, colon carcinomas, and colon metastasis cell lines in vitro. The pentapeptide Tyr-(R,S)-Aaa2-Gly-Phe-Met (18) was the most effective analogue especially against the most antitumor drug-resistant cell lines HEp-2 and SW-620. Apoptosis as a mode of cell death was confirmed in these tumor cells after exposure to pentapeptide 18.

Preparation of (R)-(1-adamantyl)glycine and (R)-2-(1-adamantyl)-2-aminoethanol: A combination of cobalt-mediated β-ketoester alkylation and enzyme-based aminoalcohol resolution

Alkylation of the cobalt(II) complex of ethyl acetoacetate with 1-bromoadamantane affords ethyl 2-(1-adamantyl)acetoacetate, which was converted into rac-(1-adamantyl)glycine 1 and rac-2-(1-adamantyl)-2-aminoethanol 7. This was separated into enantiomers by means of vinyl acetate in the presence of Pseudomonas cepacea. Configuration R was assigned to the enantiomerically pure aminoalcohol (R)-7 on the basis of X-ray diffraction data. Further oxidation of N-protected aminoalcohol (R)-8 afforded enantiomerically pure amino acid (R)-1.

α-AMINO ACIDS IN THE ADAMANTANE SERIES. I. SYNTHESIS AND ENANTIOMERIC RESOLUTION OF 1-ADAMANTYLGLYCINE AND β-(1-ADAMANTYL)ALANINE

1-Adamantylglycine and β-(1-adamantyl)alanine have been synthesized via the amination of α-haloacids.Enantiomeric resolution of these compounds was achieved by separation of the diastereomeric salts formed between their methyl esters and d-dibenzoyltartaric acid as well as with d-camphor-10-sulfonic acid.In order to determine the absolute configurations of these amino acids, they were converted to Schiff bases and diastereomeric tetradentate Ni2+ complexes were synthesized from these derivatives.