125473-34-9

Upstream product

• 69143-05-1 (E)-4-methyl-pent-2-en-1-ol 
• 125414-63-3 4-(4S)-hydroxymethyl-5-(5R)-isopropyloxazolidin-2-one 
• 127913-28-4 (R)-2-Methyl-1-(S)-oxiranyl-propan-1-ol 
• 127889-61-6 Benzoic acid (4R,5R)-5-isopropyl-2-oxo-oxazolidin-4-ylmethyl ester 
• 82290-66-2 (2S,3S)-2-Hydroxymethyl-3-(1-methylethyl)oxirane 
• 125414-60-0 Trichloro-acetic acid (4R,5S)-5-isopropyl-2-oxo-oxazolidin-4-ylmethyl ester 
• 125414-20-2 2,2,2-Trichloro-acetimidic acid (2R,3S)-3-isopropyl-oxiranylmethyl ester 
• 125414-30-4 (1'S,4R)-4-(2'-methyl-1'-hydroxypropyl)-2-(trichloromethyl)-2-oxazoline 
• 182958-39-0 (1S,7aR)-1-Isopropyl-5,5-dimethyl-dihydro-oxazolo[3,4-c]oxazol-3-one 
• 171623-08-8 (3R)-3-<(1R)-1-hydroxy-2-methylpropyl>-1-oxa-4-azaspiro<4,5>decane-4-carboxylic acid tert-butyl ester 
• 171618-18-1 (4R)-4-((1R)-1-hydroxy-2-methyl-propyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 171623-09-9 (7'S,7'aR)-dihydroxy-7'-isopropylspirooxazolo<3,4-c>oxazol>-5'-one 
• 188802-09-7 (2R,3S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-dibenzylamino-4-methyl-pentan-3-ol 
• 188802-11-1 (2R,3S)-2-Amino-1-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentan-3-ol 

Downstream Products

• 10148-70-6 (2S,3S)-3-hydroxyleucine 

Relevant academic research and scientific papers

Stereodivergent Approach to β-Hydroxy α-Amino Acids from C2-Symmetrical Alk-2-yne-1,4-diols

(Matrix Presented) A new stereodivergent route to erythro- and threo-β-substituted serines from a common C2-symmetrical alk-2-yne-1,4-diol is described. Stereocontrol in such an acyclic system is achieved by taking advantage of symmetry. Stereo

A highly stereoselective synthesis of (2S,3S)-β-hydroxyleucine

A highly diastereoselective nucleophilic addition of Grignard reagent to N,N-dibenzyl-O-TBS-serinal 3 was the key step in the present synthesis of (2S,3S)-β-hydroxyleucine 1.

Grignard reactions to chiral oxazolidine aldehydes

Modest to high levels of asymmetric induction are observed with Grignard additions to Garner type aldehydes. The resultant secondary alcohols are important precursors of chiral building blocks for asymmetric synthesis and we have demonstrated that they can be readily converted into their respective γ-hydroxy-β-amino alcohols and β-hydroxyamino acids. Additionally, aryloxy ethers, important components of many natural products, can be obtained from these precursors.

A practical stereoselective synthesis of (2S, 3S)-3-hydroxyleucine

A practical and convenient procedure is described for the preparation of gram quantities of (2S, 3S)-3-hydroxyleucine. The key step involves the triflate-mediated cyclization of spirooxazolidine 4 to the spirobicyclic compound 5, which is easily converted to the title compound in high yield.

RAPID SYNTHESIS OF β-HYDROXY-α-AMINO ACIDS, SUCH AS L-THREONINE, β-HYDROXYPHENYLALANINE, AND β-HYDROXYLEUCINE, VIA AN APPLICATION OF THE SHARPLESS ASYMMETRIC EPOXIDATION

The optically active epoxy alcohols 6abc, prepared by a Sharpless kinetic resolution-epoxidation process, were converted to the optically pure β-hydroxy-α-amino acids 1abc in four steps and high overall yield.

Amino Acids and Peptides; 70. Optically Active α-Amino Acids, N-Boc-Aminoaldehydes and α-Amino-β-hydroxy Acids from 2,3-Epoxy Alcohols

Trichloroacetimidic esters of 2,3-epoxy alcohols are transformed into oxazolines 5 and dihydrooxazines 6, respectively, depending on the structure of the educts and the catalyst.The five-membered ring compounds 5 are transformed into erythro-α-amino-β-hydroxy acids (60-70percent from epoxy alcohols) via axazolidinones 11, 12, and 13. α-Amino acids and α-substituted α-amino acids 10 as well as the corresponding aldehydes 9 are obtained from the dihydrooxazines 6 (50-60percent from epoxy alcohols).