(2R)-2-azaniumyl-4-sulfanylbutanoate

Base Information

• Chemical Name: (2R)-2-azaniumyl-4-sulfanylbutanoate
• CAS No.: 6027-14-1
• Molecular Formula: C₄H₉NO₂S
• Molecular Weight: 135.187
• Hs Code.: 2930909090
• Mol file: 6027-14-1.mol

Synonyms:

Chemical Property of (2R)-2-azaniumyl-4-sulfanylbutanoate

Chemical Property:

• Boiling Point: 299.7±35.0 °C(Predicted)
• PKA: 2.24±0.10(Predicted)
• PSA: 102.12000
• Density: 1.259±0.06 g/cm3(Predicted)
• LogP: 0.41850
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: -2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 135.03539970
• Heavy Atom Count: 8
• Complexity: 80.6

Purity/Quality:

98.5% ^*data from raw suppliers

D-Homocysteine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CS)C(C(=O)[O-])[NH3+]
• Isomeric SMILES: C(CS)[C@H](C(=O)[O-])[NH3+]
• Uses: D-Homocysteine is a stereoisomer of L-Homocysteine (H591950) which is the hydrolysis product of adenosine (A280400), a purine nucleoside. Metabolic rate of L-Homocysteine is converted back to L-Methionine( M260440) via tetrahydrofolate.

Technology Process of (2R)-2-azaniumyl-4-sulfanylbutanoate

There total 9 articles about (2R)-2-azaniumyl-4-sulfanylbutanoate 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: 92.6%

(R)-1,3-thiazane-4-carboxylic acid (147331-82-6) → D-homocysteine (454-28-4,454-29-5,6027-13-0,6027-14-1)

Guidance literature:

With hydroxylamine hydrochloride; triethylamine; In ethanol; for 1h; Heating;

DOI:10.1246/bcsj.66.536

Reference yield: 84.1%

(4R)-1,3-thiazane-2,4-dicarboxylic acid hydrochloride → D-homocysteine (454-28-4,454-29-5,6027-13-0,6027-14-1)

Guidance literature:

With hydroxylamine hydrochloride; triethylamine; In ethanol; at 78 ℃; for 1.41667h; pH=6 - 7;

DOI:10.1248/cpb.50.1081

Reference yield: 74.1%

(2R,4R)-1,3-thiazine-2,4-dicarboxylic acid hydrochloride → D-homocysteine (454-28-4,454-29-5,6027-13-0,6027-14-1)

Guidance literature:

With hydroxylamine hydrochloride; triethylamine; In ethanol; for 1h; Heating;

DOI:10.1246/cl.2000.468

upstream raw materials:

(2S,2'S)-2-amino-4-(2'-amino-2'-carboxyethylsulfanyl)butanoic acid

D-methionine

D-homocystine

(R)-1,3-thiazane-4-carboxylic acid

Downstream raw materials:

meso-homolanthione

D-homocystine

(2R,2'S)-2-amino-4-(2'-amino-2'-carboxyethylsulfanyl)butanoic acid

(S)-5’-(S)-(3-amino-3-carboxypropyl)-5’-thioadenosine

Refernces

• 1、 Shiraiwa, Tadashi,Nakagawa, Kazuo,Kanemoto, Norito,Kinda, Tomohiro,Yamamoto, Hiroki. "Synthesis of optically active homocysteine from methionine and its use in preparing four stereoisomers of cystathionine". . p. 1081 - 1085. Retrieved 2007/10/03.
• 2、 Shiraiwa, Tadashi,Nakagawa, Kazuo,Kanemoto, Norito. "Facile synthesis of optically active homocysteine from methionine". . p. 468 - 469. Retrieved 2007/10/03.