Isovaline, 3-hydroxy-, (R*,R*)- (9CI)

Base Information

• Chemical Name: Isovaline, 3-hydroxy-, (R*,R*)- (9CI)
• CAS No.: 20182-77-8
• Molecular Formula: C₅H₁₁NO₃
• Molecular Weight: 133.147
• Mol file: 20182-77-8.mol

Synonyms:Butyricacid, 2-amino-3-hydroxy-2-methyl-, DL-erythro- (8CI); D-Isovaline, 3-hydroxy-,(3R)-rel- (9CI); DL-Isovaline, 3-hydroxy-, (R*,R*)-

Chemical Property of Isovaline, 3-hydroxy-, (R*,R*)- (9CI)

Chemical Property:

• PSA: 83.55000
• LogP: -0.13050

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Isovaline, 3-hydroxy-, (R*,R*)- (9CI)

There total 51 articles about Isovaline, 3-hydroxy-, (R*,R*)- (9CI) 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: 89.4%

(2S,3R)-2-Amino-3-hydroxy-2-methyl-butyric acid isobutyl ester (211805-88-8) → (2S,3R)-α-methylthreonine (127126-06-1,20182-77-8,25580-38-5)

Guidance literature:

With sodium hydroxide; In methanol; for 3h; Ambient temperature;

DOI:10.1021/jo971983u

Reference yield: 33.0%

(2S,3S,5S)-5-benzyl-2,3-dimethyl-6-oxomorpholine-3-carbonitrile (161109-64-4) → (2R,3S)-2-amino-3-hydroxy-2-methylbutyric acid (127060-92-8,20182-77-8,25580-38-5)

Guidance literature:

(2S,3S,5S)-5-benzyl-2,3-dimethyl-6-oxomorpholine-3-carbonitrile; With tert-butylhypochlorite; In diethyl ether; at 0 - 20 ℃; for 2h;

With triethylamine; In diethyl ether; at 0 - 20 ℃; for 20h;

With hydrogenchloride; at 0 - 80 ℃; for 72h;

DOI:10.1016/j.bmc.2004.03.042

Reference yield:

acetaldehyde (75-07-0,9002-91-9) + rac-Ala-OH (302-72-7,25191-17-7,18875-37-1) → 2-amino-3-hydroxy-2-methylbutanoic acid (10148-74-0,20182-77-8,25580-38-5) + 2-amino-3-hydroxy-2-methylbutanoic acid (10148-74-0,20182-77-8,25580-38-5)

Guidance literature:

With recombinant C-terminal His₄-tagged Aeromonas jandaei L-allo-threonine aldolase; pyridoxal 5'-phosphate; water; at 30 ℃; for 24h; pH=8; optical yield given as %de; diastereoselective reaction; aq. phosphate buffer; Enzymatic reaction;

DOI:10.1002/anie.200904395

upstream raw materials:

copper(II) alaninate

acetaldehyde

(4S,5S)-4,5-Dihydro-4,5-dimethyl-2-phenyloxazol-4-carbonsaeure-methylester

(2S,5S,1'S)-5-(1'-Hydroxyethyl)-3,5-dimethyl-4-oxoimidazolidin-1-carbonsaeure-t-butylester

Refernces

• 1、 Dietz, Friedrich R.,Groeger, Harald. "Asymmetric synthesis of all stereoisomers of a-methylthreonine using an organocatalytic steglich rearrangement reaction as a key step". experimental part. p. 4208 - 4218. Retrieved 2011/04/12.
• 2、 Avenoza, Alberto,Busto, Jesus H.,Corzana, Francisco,Peregrina, Jesus M.,Sucunza, David,Zurbano, Maria M.. "α-Methylserinals as an access to α-methyl-β-hydroxyamino acids: Application in the synthesis of all stereoisomers of α- methylthreonine". . p. 719 - 724. Retrieved 2007/10/03.