122535-98-2Relevant academic research and scientific papers
Development of a practical and scalable synthesis of (R)- and (S)-3-amino-2-[(benzyloxy)methyl]propan-1-ol monohydrochloride: A useful C-4 Chiral Building Block
Yoshida, Shinya,Obitsu, Kazuyoshi,Hayashi, Yasumasa,Shibazaki, Mitsuyoshi,Kimura, Takenori,Takahashi, Takumi,Asano, Toru,Kubota, Hirokazu,Mukuta, Takashi
, p. 1527 - 1537 (2013/02/23)
The development of a practical and scalable synthesis of a C-4 chiral amine building block (R)-1·HCl and (S)-1·HCl is described. This important chiral intermediate (R)-1·HCl is efficiently synthesized from the commercially available, inexpensive, and simple 2-(hydroxymethyl)-1,3- propanediol (31) using lipase-catalyzed enantioselective hydrolysis as a key reaction. Development resulted in a telescoped process that was operated successfully and reproducibly in a pilot-plant-scale synthesis, and 22 kg of chiral amine (R)-1·HCl was prepared in the first scale-up synthesis. This synthetic method is also useful for preparation of the important chiral building block (S)-1·HCl, which is the enantiomer of (R)-1·HCl.
Chemoenzymatic Preparation of Asymmetrized Tris(hydroxymethyl)methane (THYM*) and of Asymmetrized Bis(hydroxymethyl)acetaldehyde (BHYMA*) as New Highly Versatile Chiral Building Blocks
Guanti, Giuseppe,Banfi, Luca,Narisano, Enrica
, p. 1540 - 1554 (2007/10/02)
A series of asymmetrized tris(hydroxymethyl)methanes 2 and bis(hydroxymethyl)acetaldehydes 3 have been prepared in both enantiomeric forms through a chemoenzymatic methodology.The key step is the highly enantioselective PPL-catalyzed monohydrolysis of 2(E)-alkenyl-1,3-diacetoxypropanes 25-27.A careful study on the effect of unsaturations adjacent to the prochiral center in a series of 2-substituted 1,3-diacetoxypropanes has confirmed the suggested beneficial effect of a ? system in that position but has also unveiled an unprecedented dramatic effect of double-bond configuration on enantioselectivity.A new empirical model for the interpretation of these and other results, based both on polarity and steric arguments, is proposed.This study provides a general protocol for the efficient synthesis of asymmetrized 1,3-propanediols bearing in position 2 saturated or unsaturated carbon chains.
ENZYMES AS SELECTIVE REAGENTS IN ORGANIC SYNTHESIS: ENANTIOSELECTIVE PREPARATION OF "ASYMMETRIZED tris(HYDROXYMETHYL)METHANE"
Guanti, Giuseppe,Banfi, Luca,Narisano, Enrica
, p. 2697 - 2698 (2007/10/02)
A new C-4 chiral building block, that is a tris(hydroxymethyl)methane derivative where the three equivalent hydroxymethyl groups have been differentiated *>, was prepared with excellent enantioselection, through PPL catalysed monohydroly
