86695-06-9

Usage

Chemical Properties

White powder

InChI:InChI=1/C17H21NO/c1-13(2)16(18)17(19,14-9-5-3-6-10-14)15-11-7-4-8-12-15/h3-13,16,19H,18H2,1-2H3/t16-/m1/s1

Upstream product

• 640-68-6 D-Val-OH 
• 7146-15-8 D-Valine methyl ester hydrochloride 
• 223906-36-3 (2R)-N-Boc-2-amino-1,1-diphenyl-3-methylbutanol 
• 57728-40-2 (-)-2-amino-3-methyl-1,1-diphenylbutanol 
• 106391-85-9 (R)-methyl 2-((tert-butoxycarbonyl)amino)-3-methylbutanoate 

Relevant academic research and scientific papers

Addition of the Lithium Anion of Diphenylmethanol Methyl/Methoxymethyl Ether to Nonracemic Sulfinimines: Two-Step Asymmetric Synthesis of Diphenylprolinol Methyl Ether and Chiral (Diphenylmethoxymethyl)amines

Addition of the lithium anion generated from diphenylmethanol methyl and methoxymethyl ether to nonracemic sulfinimines afforded the corresponding addition products in excellent diastereoselctivity and yields. Deprotection of the MOM as well as sulfinyl groups rendered the enantiopure (diphenylhydroxymethyl)amines in excellent yields. The procedure was applied for a two-step synthesis of diphenylprolinol, a privileged ligand in asymmetric catalysis.

COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS

The present invention relates to derivatized cyclofructan compounds, compositions comprising derivatized cyclofructan compounds, and methods of using compositions comprising derivatized cyclofructan compounds for chromatographic separations of chemical species, including enantiomers. Said compositions may comprise a solid support and/or polymers comprising derivatized cyclofructan compounds.

Diastereoselective reduction of a chiral N-Boc-protected δ-amino-α,β-unsaturated γ-keto ester Phe-Gly dipeptidomimetic

The readily available N-Boc-protected δ-amino α,β-unsaturated γ-keto ester 1 was diastereoselectively reduced to the corresponding alcohols 2 and 3, using boron- and aluminum-based reducing reagents. Reduction reactions were successful and resulted in anti/syn ratios of alcohols of >95:5 (80% yield), using LiAlH(O-t-Bu)3 in EtOH at -78 °C under chelation control, and 5:95 (98% yield), using NB-Enantride in THF at -78 °C under Felkin-Anh control.

Asymmetric Synthesis Using Chirally Modified Borohydrides. Part 3. Enantioselective Reduction of Ketones and Oxime Ethers with Reagents Prepared from Borane and Chiral Amino Alcohols

The asymmetric reduction of aromatic and aliphatic ketones, halogeno ketones, keto esters, and ketone oxime ethers with reagents prepared from borane and chiral amino alcohols has been investigated.When α,α-diphenyl-β-amino alcohols, such as (2S,3R)-(-)-2-amino-3-methyl-1,1-diphenylpentanol (2d), were used as a chiral auxiliary, very high enantioselectivities (ca. 90percent e.e.) were obtained in the reduction of various ketones and oxime ethers.

Asymmetric Reduction of Aromatic Ketones with the Reagent prepared from (S)-(-)-2-Amino-3-methyl-1,1-diphenylbutan-1-ol and Borane

Asymmetric reduction of prochiral aromatic ketones with the reagent prepared from (S)-(-)-2-amino-3-methyl-1,1-diphenylbutan-1-ol and borane afforded the corresponding aromatic secondary alcohols in high optical (94-100percent enantiomeric exces