- 4-Cyano-2-butenyl group: A new type of protecting group in oligonucleotide synthesis via phosphoramidite approach
-
4-Cyano-2-butenyl (CB) is a new type of protecting group for the internucleotide bonds in the synthesis of oligodeoxyribonucleotides by the phosphoramidite approach. This group is stable to acidic conditions and can be removed under mild conditions by a δ-elimination pathway using aqueous ammonium hydroxide.
- Ravikumar, Vasulinga T.,Cheruvallath, Zacharia S.,Cole, Douglas L.
-
-
Read Online
- 4-Cyano-2-butenyl group: A new type of protecting group in oligonucleotide synthesis via phosphoramidite approach
-
4-Cyano-2-butenyl (CB) is a new type of protecting group for the internucleotidic bonds in the synthesis of oligodeoxyribonueleotides by the phosphoramidite approach. This group is stable to acidic conditions and can be removed under mild conditions by a δ-elimination pathway using aqueous ammonium hydroxide.
- Ravikumar, Vasulinga T.,Cheruvallath, Zacharia S.,Cole, Douglas L.
-
-
Read Online
- Synthesis of 2,5-substituted tetrahydrofurans by Pd(II)-catalyzed cyclization
-
The Pd(II)-catalyzed cyclization of hydroxyl-substituted allylic alcohols quantitatively afforded a cis/trans mixture of 2,5-substituted tetrahydrofurans.
- Olszewska, Beata,Kryczka, Boguslaw,Zawisza, Anna
-
-
Read Online
- A Facile Synthesis of the Sex Pheromone of the Cabbage Looper Trichoplusia ni
-
The sex pheromone of the cabbage looper Trichoplusia ni Hubner, (Z)-7-dodecen-1-yl acetate, was synthesized via a bimolecular nucleophilic substitution reaction between the Grignard reagent of the protected bromohydrin with (Z)-2-hepten-1-yl acetate in the presence of CuI catalyst as a key step. An efficient synthetic method of preparation of the pheromone was achieved from (Z)-2-butene-1,4-diol in four steps with an overall yield of 22.1%.
- Nguyen, Thanh-Danh,Nguyen, Cong-Hao,Im, Chan,Dang, Chi-Hien
-
p. 877 - 879
(2017/03/15)
-
- Ligand-Controlled Regiodivergence in the Copper-Catalyzed [2,3]- and [1,2]-Rearrangements of Iodonium Ylides
-
Despite the importance of allylic ylide rearrangements for the synthesis of complex molecules, the catalyst control of [2,3]- and [1,2]-rearrangements remains an unsolved problem. We developed the first regiodivergent [2,3]- and [1,2]-rearrangements of iodonium ylides that are controlled by copper catalysts bearing different ligands. In the presence of a 2,2′-dipyridyl ligand, diazoesters and allylic iodides react via a [2,3]-rearrangement pathway. Alternatively, a phosphine ligand favors the formation of the [1,2]-rearrangement product. A series of α-iodoesters containing a broad range of functional groups were obtained in high yields, regioselectivities, and diastereoselectivities. Deuterium-labeling studies suggest distinct mechanisms for the regioselective rearrangements.
- Xu, Bin,Tambar, Uttam K.
-
supporting information
p. 12073 - 12076
(2016/09/28)
-
- Total synthesis of photoactivatable or fluorescent anandamide probes: Novel bioactive compounds with angiogenic activity
-
Endocannabinoids are endogenous polyunsaturated fatty acids involved in a multitude of health and disease processes. Recently, several lines of evidence suggest the presence of a novel non-CB1/CB2 anandamide receptor in endothelial cells. Thus, we synthes
- Balas, Laurence,Durand, Thierry,Saha, Sattyabrata,Johnson, Inneke,Mukhopadhyay, Somnath
-
scheme or table
p. 1005 - 1017
(2009/12/24)
-
- Syntheses of 5-chlorouracils/thymines with 1-[phosphono(methyl/ difluoromethyl)]-1,2-unsaturated-moiety-substituted methyl groups at N(1) and human thymidine phosphorylase inhibitory activity
-
By attaching (methyl)- or (difluoromethyl)-phosphonate groups to the 1-positions of ethene, cyclopentene or benzene, and attaching 1-(methyl)-5-chlorouracil or 1-(methyl)thymine groups to the corresponding 2-positions, compounds 1 - 5 were prepared as pot
- Birck, Matthew R.,Clinch, Keith,Gainsford, Graeme J.,Schramm, Vern L.,Tyler, Peter C.
-
experimental part
p. 823 - 838
(2009/08/14)
-
- Synthesis of [3H](4-fluorobutyl)propyl[2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)pyrrolo[2,3-d]pyrimidin-4-yl]amine: A potent radioligand for corticotropin-releasing hormone type 1 receptor
-
[3H](4-Fluorobutyl)propyl[2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)pyrrolo[2,3-d]pyrimidin-4-yl]amine ([3H]LWH-154), a novel potent radiolabelled analog of the nonpeptide corticotropin-releasing hormone type 1 receptor (CRHR1/s
- Hsin, Ling-Wei,Webster, Elizabeth L.,Chrousos, George P.,Gold, Philip W.,Eckelman, William C.,Contoreggi, Carlo,Rice, Kenner C.
-
p. 899 - 908
(2007/10/03)
-
- The chemistry of metallacyclic alkenylcarbene complexes: Part 9. Synthesis and reactions of chelated η2-alkene- and η3-allyl-carbene complexes of cobalt, manganese and chromium
-
Cobaltalactams 7 with alkyl substituents at the nitrogen atom are accessible by UV-irradiation of CpCo(CO)2 6 in the presence of the appropriate vicinal aminoalkenol 8. Thus chelated (η3-allyl)cobaltcarbene complexes with either (endo-amino)oxo (3), (exo-amino)oxo (11), or dioxo (2) substitution at the carbene carbon atom are now available. A synthetic route to chelated (η2-alkene)-carbene complexes of chromium with allylically situated hydroxy groups is also presented.
- Eigemann, Sven-Eric,Schobert, Rainer
-
p. 115 - 126
(2007/10/03)
-
- An improved method for the preparation of 4-cyano-2-butenyl- deoxyribonucleosidephosphoramidites
-
An improved alternative synthesis of 4-cyano-2-butenyldeoxy nucleosidephosphoramidites in >100g quantities is described via reaction of the phosphordiamidites with 4-cyano-2-buten-1-ol.
- Duckworth,Ackroyd
-
p. 1227 - 1229
(2007/10/03)
-
- A mild convenient Barbier-type allylation of aldehydes to homoallylic alcohols via iodide ion promoted stannylation of allylic bromides and chlorides with tin(II) chloride
-
Barbier-type allylation of aldehydes with allylic bromides and tin(II) chloride dihydrate is largely accelerated by adding stoichiometric or substoichiometric amounts of sodium iodide. This method has some merits such as lower temperature, shorter reaction time and/or more choices of solvents for the reaction. Moreover, the activation by the iodide ion enables the use of relatively unreactive allylic chlorides of various structural types (e.g., 3-chloro-2-chloromethylpropene as an isobutene dianion equivalent) and, thus, expands synthetic applicability of this reaction. The major role of the iodide salt is attributed to the in situ generation of the corresponding allylic iodide.
- Imai,Nishida
-
p. 395 - 399
(2007/10/02)
-
- Diastereoselective α Allylation of Secondary and Tertiary Thioamides via Thio-Claisen Rearrangement. A Structural Proof of Z Secondary Thioamide Dianions and Z Tertiary Thioamide Anions
-
Highly diastereoselective α allylation of secondary and tertiary thioamides is achieved by making use of thio-Claisen rearrangement.From the correlation between the diastereoselectivities in products and the structures of allylating agents, the Z structures of secondary thioamide dianion (ca. 100percent Z) and tertiary thioamide anion (>97percent Z) are concluded.
- Tamaru, Y.,Furukawa, Y.,Mizutani, M.,Kitao, O.,Yoshida, Z.
-
p. 3631 - 3639
(2007/10/02)
-