120205-50-7Relevant articles and documents
Synthesis of both syn and anti diastereoisomers of Boc-dolaproine from (S)-proline through DKR using ruthenium-catalyzed hydrogenation: A dramatic role of N-protecting groups
Mordant, Céline,Reymond, Sébastien,Ratovelomanana-Vidal, Virginie,Genêt, Jean-Pierre
, p. 9715 - 9723 (2004)
The natural (2R,3R)-Boc-dolaproine and its unnatural (2S,3S) diastereoisomer were synthesized involving as key transformation the Ru(II)-promoted hydrogenation of the β-keto-α-methyl ester derived from (S)-N-Boc-proline. Interestingly, the asymmetric hydrogenation of this β-keto ester N-protected as an amine hydrochloride salt, provided the corresponding anti (2S,3R)- and (2R,3S)-β-hydroxy-α-methyl esters with significant level of selectivities through dynamic kinetic resolution. Graphical Abstract.
An easy and stereoselective synthesis of N-Boc-dolaproine via the Baylis-Hillman reaction
Almeida, Wanda P.,Coelho, Fernando
, p. 937 - 940 (2003)
In this communication we report a stereoselective total synthesis of N-Boc-dolaproine (Dap), an amino acid residue of the antineoplastic pentapeptide Dolastatin 10. Our strategy is based on a Baylis-Hillman reaction between N-Boc-prolinal and methyl acrylate, followed by a diastereoselective double bond hydrogenation and hydrolysis of the ester function.
EFFICIENT PREPARATION OF DOLASTATIN AND AURISTATIN ANALOGS THROUGH A COMMON INTERMEDIATE
-
Paragraph 0087, (2021/09/17)
Methods for making a dolastatin, auristatin or related compounds comprising the steps of providing a universal dolastatin core of Formula (I) reacting the C-terminal carboxylic acid group with an amine (A) to form an amide bond and reacting the N-terminal amine with a carboxylic acid (CA) to form an amide bond, wherein the steps can be performed in either order. Also provided are an isolated salt of the universal dolastatin core for use in preparation of dolastatins, auristatins and related compounds. Also provided are a number of intermediates and process steps which are useful for the preparation of high purity dolastatin core and high purity dolastatin and auristatin compounds.
Synthesis method of N-Boc-Dolaproine and synthesis method of Boc-Dap DCHA
-
, (2020/07/21)
The invention discloses a synthesis method of N-Boc-Dolaproine and a synthesis method of Boc-Dap DCHA. The synthesis method comprises the following steps: 1) subjecting a compound shown in the specification and a compound shown in the specification to a Reformatsky reaction under the activation of zinc powder to synthesize a compound shown in the specification, with X being Cl or Br or I, and R being alkane or olefin; 2) subjecting the compound shown in the specification to methylation to obtain a compound shown in the specification; 3) carrying out a hydrolysis reaction on the compound shownin the specification so as to obtain N-Boc-Dolaproine. By applying the technical scheme of the invention, the yield of each step of reaction is relatively good, the intermediates are easy to purify, the process route used by the method is relatively short, the material price is relatively low, the synthesis process is simple to operate, the production cost is further reduced, and the methods can be applied to industrial production.