905929-81-9

Basic information

• Product Name: D-METHALLYLGLYCINE
• Synonyms: D-METHALLYLGLYCINE;(R)-2-Methallylglycine
• CAS NO: 905929-81-9
• Molecular Formula: C6H11NO2
• Molecular Weight: 129.16
• Mol File: 905929-81-9.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• CAS DataBase Reference: D-METHALLYLGLYCINE(CAS DataBase Reference)
• NIST Chemistry Reference: D-METHALLYLGLYCINE(905929-81-9)
• EPA Substance Registry System: D-METHALLYLGLYCINE(905929-81-9)

Safety Data

• Hazardous Substances Data: 905929-81-9(Hazardous Substances Data)

Usage

General Description

D-Methallylglycine, also known as D-MAG, is a non-proteinogenic amino acid that is used in the synthesis of pharmaceuticals and other organic compounds. It is a derivative of methallylglycine, an amino acid found in certain plant species, and is commonly used as a building block in the production of various drugs and other chemical products. D-MAG has also been studied for its potential role in the treatment of certain medical conditions, as it has been shown to have anti-bacterial properties and may also have application in the field of crop protection.

Upstream product

• 87325-65-3 (R,S)-2-acetamido-4-methyl-4-pentenoic acid 
• 1461642-01-2 (2R,R_S)-2-(tert-butylsulfinamido)-4-methylpent-4-enoic acid 
• 1461642-02-3 (2S,S_S)-2-(tert-butylsulfinamido)-4-methylpent-4-enoic acid 
• 121704-04-9 2-(2-Methoxy-acetylamino)-4-methyl-pent-4-enoic acid 
• 1575-67-3 2-(2-methyl-allyl)-malonic acid diethyl ester 
• 80741-44-2 ethyl 2-<(diphenylmethylene)amino>-4-methyl-(+/-)-4-pentenoate 
• 4746-62-7 2-amino-2-hydroxyacetic acid 
• 167773-10-6 4,4,5,5-tetramethyl-2-(2-methylallyl)-1,3,2-dioxaborolane 
• 68843-73-2 ethyl (2RS)-2-amino-4-methyl-4-pentenoate 
• 31918-40-8 2-Oximino-4-methyl-4-pentensaeure 
• 31918-30-6 2-Oximino-4-methyl-4-pentensaeureethylester 
• 20850-33-3 ethyl 2-acetamido-2-cyano-4-methyl-4-pentenoate 
• 181826-55-1 (S)-2-Benzyloxyamino-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-4-methyl-pent-4-en-1-one 
• 87325-69-7 tert-butyl (2S)-2-amino-4-methylpent-4-enoate 

Downstream Products

• 87720-55-6 N-fluoren-9-ylmethyloxycarbonyl-4,5-dehydro-L-leucine 
• 87325-47-1 (2S)-2-tert-butoxycarbonylamino-4-methyl-4-pentenoic acid 
• 131177-58-7 Fmoc-4,5-didehydro-DL-leucine 

Relevant articles and documents

ANTHELMINTIC DEPSIPEPTIDE COMPOUNDS

The present invention provides cyclic depsipeptide compounds of formula (I) wherein the stereochemical configuration of at least one carbon atom bearing the groups Cy1, Cy2, R1, R2, R3, R4, Ra and Rb is inverted compared with the naturally occurring cyclic depsipeptide PF1022A. The invention also provides compositions comprising the compounds that are effective against parasites that harm animals. The compounds and compositions may be used for combating parasites in or on mammals and birds. The invention also provides for an improved method for eradicating, controlling and preventing parasite infestation in birds and mammals.

Diastereoselective amidoallylation of glyoxylic acid with chiral tert-butanesulfinamide and allylboronic acid pinacol esters: Efficient synthesis of optically active γ,δ-unsaturated α-amino acids This work is dedicated to Dr. Masanori Sakamoto, Professor Emeritus of Meiji Pharmaceutical University, on the occasion of his 77th birthday (KIJU)

A convenient synthesis of δ,γ-unsaturated amino acids has been developed. After a mixture of (R)-tert-butanesulfinamide and glyoxylic acid with molecular sieves in CH2Cl2 was stirred for 42 h at room temperature, allylboronic acid pinacol ester was added to the mixture to give (R)-2-((R)-tert-butanesulfinamido)pent-4-enoic acid with high diastereoselectivity. The corresponding reaction of (Z)-crotylboronic acid pinacol ester produced no product; however, that of (E)-crotylboronic acid pinacol ester produced (2R,3S)-2-((R)-tert-butylsulfinamido)-3-methylpent-4- enoic acid with excellent diastereoselectivity.

Direct synthesis of unprotected α-amino acids via allylation of hydroxyglycine

Hydroxyglycine, the ammonia adduct of glyoxylic acid, was found to react with various allylboronates in the presence of triethylamine in methanol to give unprotected α-amino acids directly with high stereoselectivity. For instance, the reactions with (E)- and (Z)-crotylboronates afforded the corresponding anti- and syn-crotylated products (isoleucine and alloisoleucine after hydrogenation) with high diastereoselectivity, respectively. Interestingly, it was found that isomerization of the products (γ-adducts to α-adducts) occurred under the reaction conditions in some cases. Control experiments have suggested that the isomerization took place via 2-aza (or azonia) Cope rearrangement of imines derived from γ-adducts and glyoxylic acid.