709031-30-1

Basic information

• Product Name: Hydroxyl-adaMantyl-glycine
• Synonyms: Hydroxyl-adaMantyl-glycine;alpha-Amino-3-hydroxy-tricyclo[3.3.1.1(3,7)]decane-1-acetic acid
• CAS NO: 709031-30-1
• Molecular Formula: C12H19NO3
• Molecular Weight: 225.28416
• Mol File: 709031-30-1.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 401.967 °C at 760 mmHg
• Flash Point: 196.903 °C
• Appearance: /
• Density: 1.409
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.645
• PKA: 2.36±0.10(Predicted)
• CAS DataBase Reference: Hydroxyl-adaMantyl-glycine(CAS DataBase Reference)
• NIST Chemistry Reference: Hydroxyl-adaMantyl-glycine(709031-30-1)
• EPA Substance Registry System: Hydroxyl-adaMantyl-glycine(709031-30-1)

Safety Data

• Hazardous Substances Data: 709031-30-1(Hazardous Substances Data)

Usage

Description

Hydroxyl-adaMantyl-glycine is a complex chemical compound that features hydroxyl, adamantane, and glycine moieties within its molecular structure. This unique combination endows the compound with distinctive chemical and physical properties. The hydroxyl group confers high reactivity, allowing for diverse chemical interactions, while the adamantane moiety imparts rigidity and stability to the molecule. The glycine component enhances its solubility and biological activity, making Hydroxyl-adaMantyl-glycine a promising candidate for applications in medicinal chemistry, drug design, and materials science. Further exploration and development are essential to fully exploit the capabilities of this versatile compound.

Uses

Used in Medicinal Chemistry:
Hydroxyl-adaMantyl-glycine is used as a building block for the development of novel pharmaceuticals, leveraging its unique functional groups to create new drug candidates with potential therapeutic benefits.
Used in Drug Design:
Hydroxyl-adaMantyl-glycine is utilized as a key component in the design of innovative drugs, where its reactive hydroxyl group and stable adamantane structure can be tailored to target specific biological pathways or receptors.
Used in Materials Science:
Hydroxyl-adaMantyl-glycine is employed as a constituent in the creation of advanced materials, taking advantage of its solubility and reactivity to produce materials with specialized properties for various applications.
Further research and development are necessary to explore the full range of applications and optimize the use of Hydroxyl-adaMantyl-glycine in these industries.

InChI:InChI=1/C12H19NO3/c13-9(10(14)15)11-2-7-1-8(3-11)5-12(16,4-7)6-11/h7-9,16H,1-6,13H2,(H,14,15)

Upstream product

• 709031-28-7 3-hydroxy-α-oxotricyclo [3.3.1.1^3,7]decane-1-acetic acid 
• 420120-31-6 3-hydroxytricyclo[3.3.1.1³'⁷]decane-1-carbaldehyde 
• 1415016-18-0 C₁₉H₂₄N₂O₂S 
• 1415016-19-1 C₁₉H₂₅NO₄S 
• 618-36-0 rac-methylbenzylamine 
• 768-90-1 1-Adamantyl bromide 
• 709031-34-5 dichloro-(tricyclo[3.3.1.1^3,7]decan-1-yl)acetic acid methyl ester 
• 128665-98-5 α-hydroxytricyclo[3.3.1.1^3,7]decane-1-acetic acid methyl ester 
• 709031-35-6 dichloro-(3-hydroxy-adamantan-1-yl)-acetic acid methyl ester 
• 30074-09-0 α-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid 
• 95853-35-3 (S)-(+)-β-amino-1-adamantaneacetic acid 
• 828-51-3 1-Adamantanecarboxylic acid 
• 770-71-8 1-adamantanemethanol 
• 2094-74-8 1-Adamantanecarbaldehyde 

Relevant articles and documents

Synthetic method of saxagliptin intermediate

The invention belongs to the technical field of organic synthesis, and particularly relates to a synthetic method of a saxagliptin intermediate. The intermediate is compound I, compound A2 is taken as a raw material, and compound I is obtained through hydrolysis hydroxylation, hydrogenation and amino protecting reaction. The compound A2 is oxidized by taking 1 - adamantane methanol as a raw material. The resulting compound A2. Due to the fact that the synthetic route is shortened, the production cycle is shortened, and the production cost is greatly reduced. The compound A2 to the compound A3, the hydrolysis and the hydroxylation are synthesized in one step in one step, the amount of waste acid water is greatly reduced, and the optical chiral protecting group is kept off, and the chiral value of the final compound I is greatly improved. The whole reaction process is mild in condition, free of harsh anhydrous anaerobic reaction, greatly reduced in wastewater amount and extremely high in product optical activity.

A process for preparing hydroxy adamantane glycine derivatives

The invention aims to provide a novel and simple synthesis route of a hydroxyadamantylglycine derivative represented by the formula I, namely (aS)-a-[[(1,1-dimethylethoxy)carboxyl]-amino]-1-(3-hydroxyadamantyl)-acetic acid) or salts of the derivative through developing a novel compound. A novel compound namely 2(aS)-a-amino-1-adamantyl-acetamide represented by the formula III is taken as the primary raw material and then is subjected to hydrolysis reactions and hydroxy group introduction so as to obtain the (aS)-a-[[(1,1-dimethylethoxy)carboxyl]-amino]-1-(3-hydroxyadamantyl)-acetic acid) represented by the formula I or salts of the derivative. The invention further provides a synthesis method of the novel compound represented by the formula III. The synthesis method can solve the disadvantages that the cost of enzyme catalyzed reactions is high, the enzyme catalyzed reactions are unstable, the chemical catalysis method has a low ee value, and the reaction product is not easy to purify in the prior art, and thus is more suitable for industrial production.

Intermediates for synthesizing sand Geleg sandbank N-tert-butoxycarbonyl-3-hydroxy-1-adamantyl-D-gly method

The invention discloses a novel method of preparing an important saxagliptin intermediate N-t-butyloxycarboryl-3-hydroxyl-1-adamantyl-D-glycine. The method comprises the following steps: S1, carrying out an asymmetric reduction amination reaction on 2-(3-hydroxyl-1-adamantyl)-2-oxo-tert-butyl acetate and benzylamine under the effect of a self-made chiral acylamino alcohol catalyst, and hydrolyzing ester to obtain 3-hydroxyl-1-adamantyl-D-glycine; and S2, carrying out a reaction on 3-hydroxyl-1-adamantyl-D-glycine and di-tert-butyl dicarbonate ester to obtain N-t-butyloxycarboryl-3-hydroxyl-1-adamantyl-D-glycine. The synthetic method of the important saxagliptin intermediate N-t-butyloxycarboryl-3-hydroxyl-1-adamantyl-D-glycine provided by the invention is low in cost and available in raw materials, short in step, mild in reaction condition, simple and convenient to operate, high in synthetic efficiency, environment-friendly and suitable for industrialized production, and provides a novel path for preparing saxagliptin and intermediates thereof.