Serine, 2-(hydroxymethyl)-

Base Information

• Chemical Name: Serine, 2-(hydroxymethyl)-
• CAS No.: 17149-11-0
• Molecular Formula: C4H9NO4
• Molecular Weight: 135.12
• Mol file: 17149-11-0.mol

Synonyms:

Chemical Property of Serine, 2-(hydroxymethyl)-

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Serine, 2-(hydroxymethyl)-

There total 2 articles about Serine, 2-(hydroxymethyl)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + glycine (56-40-6,18875-39-3,25718-94-9) → serin (302-84-1,83245-15-2) + (2-amino-3-hydroxy-2-hydroxymethyl)propanoic acid (17149-11-0)

Guidance literature:

With N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid; 1,3-bis[bis(2-pyridylmethyl)aminomethyl]benzene*4HClO₄; In water; at 50 ℃; for 2h; pH=7.30;

DOI:10.1246/bcsj.75.1383

Reference yield:

→ (2-amino-3-hydroxy-2-hydroxymethyl)propanoic acid (17149-11-0) + 2-carbobenzyloxyamino-3-hydroxy-2-hydroxymethylpropionic acid (28336-88-1)

Guidance literature:

Reference yield: 67.0%

(2-amino-3-hydroxy-2-hydroxymethyl)propanoic acid (17149-11-0) + monobenzyl glutaryl N-hydroxysuccinimide (104253-38-5) → 4-(1-Carboxy-2-hydroxy-1-hydroxymethyl-ethylcarbamoyl)-butyric acid benzyl ester (178271-90-4)

Guidance literature:

With triethylamine; In dichloromethane; water; N,N-dimethyl-formamide; 1.) 0 deg C, 1 h, 2.) 0 deg C to RT, 15 h;

DOI:10.1021/ja952265x

upstream raw materials:

formaldehyd

glycine

Downstream raw materials:

4-(1-Carboxy-2-hydroxy-1-hydroxymethyl-ethylcarbamoyl)-butyric acid benzyl ester

Refernces

The total synthesis of antrimycin D(v); II: Synthesis of tetrahydropyridazinecarboxylic acid and its incorporation into peptides

10.1055/s-1993-25947

The study focuses on the synthesis of tetrahydropyridazinecarboxylic acid and its integration into peptides. The researchers used various chemicals, including di- and tripeptides containing (R, S)-tetrahydropyridazine-3-carboxylic acids, which were synthesized via protected y-formyl-a-hydrazinobutyric acids. These acids were obtained from acetals of ethyl 7-formylbutyrate or ethyl y-formyl-α-oxobutyrate. The study also involved the synthesis of non-proteinogenic amino acids such as (hydroxymethyl)serine, dehydrovaline, dehydroisoleucine, (S,S)-α,β-diaminobutyric acid, and (S)-tetrahydropyridazinecarboxylic acid. The researchers explored two approaches to synthesize tetrahydropyridazinecarboxylic acid, one involving the reduction of tert-butoxycarbonyl-hydrazones and the other using the acetal of ethyl 5-oxopentanoate. The study aimed to overcome difficulties encountered in the synthesis of peptides containing tetrahydropyridazinecarboxylic acid and to provide detailed experimental procedures for the synthesis of antrimycin D.

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