2,3-<i>O</i>-(3-Pentylidene)-D-glyceraldehyde and 2,3-<i>O</i>-(3-Pentylidene)-L-glyceraldehyde: Convenient Glyceraldehyde Surrogates Obtained via a Novel Periodate-Based Oxdation System

Schmid, Christopher R.; Bradley, David

doi:10.1055/s-1992-26170

Cited by 52 publications

(33 citation statements)

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“…To avoid the formation of this acyclic product, other oxidative cleavage conditions were explored. Our attempts, including treatment with Pb(OAc) 4 or Mn(OAc) 3 ,19 or with a combination of KIO 4 and KHCO 3 in a buffered solution at pH 7–7.5,20 either led to 25‐T or gave complex mixtures of products.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Antiviral Evaluation, and Computational Studies of Cyclobutane and Cyclobutene L‐Nucleoside Analogues

et al. 2013

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This paper describes the stereoselective synthesis of a series of functionalized cyclobutane and cyclobutene L‐nucleoside analogues featuring a methylene spacer between the carbocycle and the nucleobase. These L‐nucleoside analogues were subjected to comprehensive screening for antiviral activity. To obtain knowledge at the molecular structural level relevant for designing future analogues, the mechanism of action of these L‐nucleoside analogues as anti‐herpes simplex virus agents was investigated by computational approaches. In particular, protein–ligand docking calculations were used to rationalize the ability of the prodrug candidates to be activated. Docking experiments were performed on the three kinases involved in the activation process of thymine and guanine derivatives.

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Section: Resultsmentioning

confidence: 99%

Synthesis, Antiviral Evaluation, and Computational Studies of Cyclobutane and Cyclobutene L‐Nucleoside Analogues

et al. 2013

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“…Mandai synthesis of Tamiflu : Also, Mandai and Oshitari stated two novel routes to Tamiflu starting from chiral pools without any chromatographic purification. Aldehyde 201 prepared from D‐mannitol ( 200 ) was subjected to Grignard reaction to get alcohol and subsequent ortho ester Claisen rearrangement to develop ester 202 which after tandem acetal cleavage and ester reduction converted to a diol (Scheme ) . Protection with 3,4‐dihydro‐2 H ‐pyran (DHP) provided di‐THP ether 203 .…”

Section: Common Synthetic Approachesmentioning

confidence: 99%

Synthetic Advancement of Neuraminidase Inhibitor “Tamiflu”

2020

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Tamiflu (oseltamivir phosphate), clinically working antiviral chiral drug, is most effective against the infectious disease caused by both influenza A and B. It is also the last resort drug for the treatment of N1H1 virus infection at a high cost with minimal global availability. The current industrial method uses natural (‐)‐shikimic acid obtained from Chinese star anise and coffee beans, hence the limited natural resource and scarcity restricted the Tamiflu production. While most of the synthetic methods reported were composed of natural chiral pools and relatively low‐cost reagents, however, the industrial process is fundamentally limited to the use of hazardous azide or tedious purification methods. In case of an influenza outbreak, producing the Tamiflu according to its demand may be difficult. This document detailed the synthetic progress of chemistry over the last two decades emphasizing the starting materials, hazards of reagents, time needed, number of steps, and overall yields etc. for the interest in academia as well as industrial research.

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“…30,31 The (S) enantiomer was initially selected for synthesis because it is derived from inexpensive D-mannitol. Cleavage of 1,2,5,6-di-O-cyclohexylidene-D-mannitol (49) using conditions developed by Schmid 32 cleanly provided protected glyceraldehyde 50 (Scheme 16). Unfortunately, Takai olefination resulted in the formation of vinyl chloride 52 with moderate diastereoselection (87:13 (E):(Z)) and low yield (<40% from 49).…”

Section: Synthesis Of the Phosphonate Side Chain 2smentioning

confidence: 99%

“…Periodate cleavage of the mono(cyclohexylidene ketal) 60 according to Schmid's conditions 32 followed by homologation with Ohira's reagent (53) led to the formation of alkyne ent-51. This alkyne was then elaborated to phosphonate ent-59 in an identical manner to that described previously (vide supra).…”

Section: Synthesis Of the Phosphonate Side Chain 2smentioning

confidence: 99%

Enantioselective total synthesis of callipeltoside A: two approaches to the macrolactone fragment

Evans

Burch

et al. 2008

Tetrahedron

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The enantioselective total synthesis of callipeltoside A is described. Two syntheses of the macrolactone subunit are included: the first relies upon an Ireland-Claisen rearrangement to generate the trisubstituted olefin geometry and the second utilizes an enantioselective vinylogous aldol reaction for this purpose. Enantioselective syntheses of the sugar and chlorocyclopropane side chain fragments are also disclosed. The relative and absolute stereochemistry of this natural product was determined by fragment coupling with the two enantiomers of the side chain fragment.

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2,3-O-(3-Pentylidene)-D-glyceraldehyde and 2,3-O-(3-Pentylidene)-L-glyceraldehyde: Convenient Glyceraldehyde Surrogates Obtained via a Novel Periodate-Based Oxdation System

Cited by 52 publications

References 0 publications

Synthesis, Antiviral Evaluation, and Computational Studies of Cyclobutane and Cyclobutene L‐Nucleoside Analogues

Synthesis, Antiviral Evaluation, and Computational Studies of Cyclobutane and Cyclobutene L‐Nucleoside Analogues

Synthetic Advancement of Neuraminidase Inhibitor “Tamiflu”

Enantioselective total synthesis of callipeltoside A: two approaches to the macrolactone fragment

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