210702-67-3Relevant academic research and scientific papers
Stereoselective synthesis of marine macrolide Aspergillide D
Talakokkula, Anil,Baikadi, Karunakar,Venkat Narsaiah
, (2019/08/08)
A formal stereoselective synthesis of the naturally occurring 16-membered macrolide aspergillide D is described. The origins of the chiral centers are ribose, lactic acid and the Sharpless asymmetric epoxidation protocol. The foremost reactions involved a
Doubly diastereoselective conjugate additions of the antipodes of lithium N-benzyl-N-(α-methylbenzyl)amide to enantiopure ε-O-protected α,β-unsaturated esters derived from d-ribose
Davies, Stephen G.,Foster, Emma M.,Lee, James A.,Roberts, Paul M.,Thomson, James E.
, p. 534 - 546 (2014/05/06)
Enantiopure ε-O-silyloxy- and ε-O-benzyloxy-α,β- unsaturated esters derived from d-ribose, each containing a cis-dioxolane unit, display excellent (≥95:5 dr) levels of diastereofacial directing ability upon conjugate addition of achiral lithium N-benzyl-N-isopropylamide. In contrast to the corresponding enantiopure ε-O-silyloxy-α,β-unsaturated ester derived from l-tartaric acid, which contains a trans-dioxolane unit, the conjugate additions of the antipodes of lithium N-benzyl-N-(α- methylbenzyl)amide to its cis-configured counterpart result in doubly diastereoselective 'matched' and 'mismatched' reaction pairings in which the inherent reagent control serves to augment or oppose, respectively, the established substrate diastereocontrol.
Synthesis of beta-L-2'-deoxy nucleosides
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Page/Page column 27, (2010/02/11)
An improved process for the preparation of 2′-modified nucleosides and 2′-deoxy-nucleosides, such as, β-L-2′-deoxy-thymidine (LdT), is provided. In particular, the improved process is directed to the synthesis of a 2′-deoxynucleoside that may utilize different starting materials but that proceeds via a chloro-sugar intermediate or via a 2,2′-anhydro-1-furanosyl-nucleobase intermediate. Where an 2,2′-anhydro-1-furanosyl base intermediate is utilized, a reducing agent, such as Red-Al, and a sequestering agent, such as 15-crown-5 ether, that cause an intramolecular displacement reaction and formation of the desired nucleoside product in good yields are employed. An alternative process of the present invention utilizes a 2,2′-anhydro-1-furanosyl base intermediate without a sequestering agent to afford 2′-deoxynucleosides in good yields. The compounds made according to the present invention may be used as intermediates in the preparation of other nucleoside analogues, or may be used directly as antiviral and/or antineoplastic agents.
Homologation of allylic alcohols. An approach to cyclic and acyclic polyoxygenated compounds
Davoille, Ryan J.,Rutherford, David T.,Christie, Steven D. R.
, p. 1255 - 1259 (2007/10/03)
The combination of the Sharpless asymmetric epoxidation reaction with a sulfur ylide mediated synthesis of allylic alcohols from epoxides provides a powerful iterative process for the production of polyoxygenated compounds. The alkene installed in the sulfur ylide reaction has also been used in a number of ring closing metathesis reactions to produce highly oxygenated cyclic compounds. (C) 2000 Elsevier Science Ltd.
A de novo synthesis of ethyl 2-deoxy-L-ribosides
Jung, Michael E.,Nichols, Christopher J.
, p. 4615 - 4618 (2007/10/03)
A short (7-step) and efficient synthesis of several derivatives of 2- deoxy-L-ribose 1, e.g., the ethyl ribosides, 2abc, has been accomplished from achiral precursors.
