beta-Hydroxyleucine

Base Information

• Chemical Name: beta-Hydroxyleucine
• CAS No.: 10148-70-6
• Molecular Formula: C6H13NO3
• Molecular Weight: 147.174
• Hs Code.: 2922509090
• DSSTox Substance ID: DTXSID90426396
• Nikkaji Number: J282.067F
• Wikidata: Q27093948
• Mol file: 10148-70-6.mol

Synonyms:beta-hydroxyleucine;beta-hydroxyleucine hydrochloride, erythro-(DL)-isomer;beta-hydroxyleucine, (DL)-isomer;beta-hydroxyleucine, threo-(DL)-isomer;beta-hydroxyleucine, threo-(L)-isomer;(2S,3S)-3-hydroxyleucine;3-hydroxyleucine

Chemical Property of beta-Hydroxyleucine

Chemical Property:

• Melting Point: 223 - 225°C
• PSA: 83.55000
• LogP: 0.11550
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Methanol (Slightly), Water (Slightly, Sonicated)
• XLogP3: -2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 147.08954328
• Heavy Atom Count: 10
• Complexity: 124

Purity/Quality:

98%,99%, ^*data from raw suppliers

(2S,3S)-3-Hydroxyleucine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(C(=O)O)N)O
• Isomeric SMILES: CC(C)[C@@H]([C@@H](C(=O)O)N)O

Technology Process of beta-Hydroxyleucine

There total 107 articles about beta-Hydroxyleucine 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: 99.0%

(4S,5S)-5-Isopropyl-2-oxazolidinone-4-carboxylic acid (125473-34-9) → (2S,3S)-3-hydroxyleucine (10148-70-6)

Guidance literature:

With hydrogenchloride; Dowex-50W (200-400) ion exchange resin; 1.) 100 deg C;

DOI:10.1016/0040-4039(95)01456-R

Reference yield: 94.0%

(2S,3S)-N-benzyl-3-hydroxyleucine (128053-01-0) → (2S,3S)-3-hydroxyleucine (10148-70-6)

Guidance literature:

With hydrogen; palladium hydroxide - carbon; In methanol; acetic acid; for 10h; under 2068.6 Torr; Ambient temperature;

DOI:10.1016/S0040-4039(00)61763-X

Reference yield: 92.0%

(2S,3S)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-4-methyl-pentanoic acid (779337-23-4) → (2S,3S)-3-hydroxyleucine (10148-70-6)

Guidance literature:

With hydrazine; In ethanol; for 2h; Heating;

DOI:10.1021/ol0485417

upstream raw materials:

(+/-)-erythro-2-bromo-3-hydroxy-4-methyl-valeric acid

N-Benzyl-DL-erythro-β-hydroxy-leucin

isobutyraldehyde

glycine

Downstream raw materials:

(+/-)-erythro-2-benzamino-3-hydroxy-4-methyl-valeric acid

(2S,3S)-3-hydroxyleucine methyl ester

rac-threo-3-Hydroxyleucin-N-sulfamat Natriumsalz

(2S,3S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-4-methyl-pentanoic acid

Refernces

• 1、 Belokon, Yuri N.,Kochetkov, Konstantin A.,Ikonnikov, Nikolai S.,Strelkova, Tatiana V.,Harutyunyan, Syuzanna R.,Saghiyan, Ashot S.. "A new synthesis of enantiomerically pure syn-(S)-β-hydroxy-α-amino acids via asymmetric aldol reactions of aldehydes with a homochiral Ni(II)-glycine/(S)-BPB Schiff base complex". . p. 481 - 485. Retrieved 2001.
• 2、 Williams, Lorenzo,Zhang, Zhongda,Ding, Xiaobin,Joullie, Madeleine M.. "A practical stereoselective synthesis of (2S, 3S)-3-hydroxyleucine". . p. 7031 - 7034. Retrieved 1995.
• 3、 Sheehan,J.C. et al.. "-". . p. 1303 - 1305. Retrieved 1962.
• 4、 Kaur, Harveen,Harris, Paul W. R.,Little, Peter J.,Brimble, Margaret A.. "Total synthesis of the cyclic depsipeptide YM-280193, a platelet aggregation inhibitor". . p. 492 - 495. Retrieved 2015.
• 5、 Raju, Ritesh,Khalil, Zeinab G.,Piggott, Andrew M.,Blumenthal, Antje,Gardiner, Donald L.,Skinner-Adams, Tina S.,Capon, Robert J.. "Mollemycin A: An antimalarial and antibacterial glyco-hexadepsipeptide- polyketide from an Australian marine-derived streptomyces sp. (CMB-M0244)". . p. 1716 - 1719. Retrieved 2014.
• 6、 Buller, Andrew R.,Doyon, Tyler J.,Grieger, Abbigail M.,Kim, Maeve,Kumar, Prasanth,Madigan, Cormac,Stitgen, Abigail,Thein, Sierra,Willoughby, Patrick H.. "Scalable and Selective β-Hydroxy-α-Amino Acid Synthesis Catalyzed by Promiscuous l-Threonine Transaldolase ObiH". . . Retrieved 2021/11/23.
• 7、 Fan, Shiming,Liu, Shouxin,Zhu, Sufang,Feng, Juan,Zhang, Zhiwei,Huang, Jing. "Temperature-Dependent Enantio- and Diastereodivergent Synthesis of Amino Acids with One or Multiple Chiral Centers". supporting information. p. 4660 - 4663. Retrieved 2017/09/11.