2831-86-9Relevant academic research and scientific papers
Ligand-controlled cobalt-catalyzed remote hydroboration and alkene isomerization of allylic siloxanes
Huang, Jiaxin,Li, Jie,Yang, Wen,Zhang, Kezhuo,Zhao, Pei,Zhao, Wanxiang
, p. 302 - 305 (2022/01/03)
The Co-catalyzed remote hydroboration and alkene isomerization of allylic siloxanes were realized by a ligand-controlled strategy. The remote hydroboration with dcype provided borylethers, while xantphos favored the formation of silyl enol ethers.
Synthesis of C -glycoside analogues of α-galactosylceramide via linear allylic C-H oxidation and allyl cyanate to isocyanate rearrangement
Liu, Zheng,Bittman, Robert
supporting information; scheme or table, p. 620 - 623 (2012/03/22)
C-Glycoside analogues of α-galactosylceramide were synthesized in which several significant modifications known to promote Th-1 cytokine production were included. The key transformations include C-H oxidation, Sharpless asymmetric epoxidation, olefin cros
Ring-opening hydrofluorination of 2,3- and 3,4-epoxy amines by HBF 4·OEt2: Application to the asymmetric synthesis of (S, S)-3-deoxy-3-fluorosafingol
Cresswell, Alexander J.,Davies, Stephen G.,Lee, James A.,Morris, Melloney J.,Roberts, Paul M.,Thomson, James E.
experimental part, p. 4617 - 4627 (2011/07/30)
Treatment of a range of 2,3- and 3,4-epoxy amines with HBF 4·OEt2 at room temperature results in fast and efficient SN2-type ring-opening hydrofluorination to give stereodefined amino fluorohydrins. Operational simplicity, scalability, and short reaction time at ambient temperature are notable features of this method. The utility of this methodology is exemplified in a concise asymmetric synthesis of (S,S)-3-deoxy-3-fluorosafingol.
An improved two-step synthetic route to primary allylic alcohols from aldehydes
Liu, Zheng,Gong, Yaqiong,Byun, Hoe-Sup,Bittman, Robert
experimental part, p. 470 - 475 (2010/06/14)
An improved two-step synthetic route to allylic alcohols from aldehydes has been developed. A modification of the HWE reaction in H2O-2-PrOH (1 : 1) and a convenient protocol to prepare AlH3 in THF from LiAlH 4 and n-BuBr are the key factors in the improvement.
Asymmetric total syntheses of spisulosine, its diastereo- and regio-isomers
Dinda, Subal Kumar,Das, Sajal Kumar,Panda, Gautam
experimental part, p. 9304 - 9309 (2011/01/12)
Starting from palmityl alcohol, divergent stereoselective syntheses of spisulosine and its diastereo- and regio-isomers have been achieved. In the Sharpless asymmetric dihydroxylation-based approach, the key step is the synthesis of monoprotected diol, whereas Miyashita's boron-directed C-2 regioselective azidolysis of enantiomerically pure epoxy alcohol is the vital step in the Sharpless asymmetric epoxidation-based route. The latter approach involves the first protecting-group-free synthesis of spisulosine.
Synthesis and antioxidant properties of an unnatural plasmalogen analogue bearing a trans O-vinyl ether linkage
Lankalapalli, Ravi S.,Eckelkamp, Joseph T.,Sircar, Debajit,Ford, David A.,Subbaiah, Papasani V.,Bittman, Robert
supporting information; experimental part, p. 2784 - 2787 (2009/12/05)
To assess the antioxidant behavior of trans-1, we first synthesized trans-allyl ether 4 by opening an (S)-glycildol derivative with an (E)-alk-2en-ol, and then produced the unnatural E-enol ether 1 by a stereoselective iridium(I)-catalyzed olefin isomerization. Natural cis-1 was preferentially degraded by HOCI and was more protective than trans-1 against lipid peroxidation Induced by a free-radical Initiator, demonstrating that the geometry of the 1-alkenyloxy bond participates In the antioxidant defensive role of 1.
A stereoselective synthesis of dihydrosphingosine
Fernandes, Rodney A.,Kumar, Pradeep
, p. 3447 - 3449 (2007/10/03)
A highly enantioselective synthesis of D-(+)-erythro-dihydrosphingosine (sphinganine) as its triacetate derivative 10, starting from palmityl alcohol (3) and employing the Sharpless asymmetric dihydroxylation as the key step, is described.
Pheromone synthesis, CLXXV: Synthesis of koiganal I and II, the sex pheromone components of the webbing clothes moth
Takikawa, Hirosato,Takenaka, Motonobu,Mori, Kenji
, p. 139 - 140 (2007/10/03)
Koiganal I [(E)-2-octadecenal (1)] and II [(2E,13Z)-2,13-octadecadienal (2)], the female-produced pheromone components of the webbing clothes moth (Tineola bisselliella), were synthesized. VCH Verlagsgesellschaft mbH, 1997.
Synthesis of Sphingosine Relatives, XIV. A New Synthesis of Symbioramide, a Ca(++)-ATPase Activator from Symbiodinium sp.
Mori, Kenji,Uenishi, Keiji
, p. 41 - 48 (2007/10/02)
Symbioramide was synthesized from D-erythro-dihydrosphingosine (19) and (R,E)-2'-tert-butyldimethylsilyloxy-3'-octadecenoic acid (14), which was prepared from (E)-2-octadecen-1-ol (4) by employing the Sharpless asymmetric epoxidation.The (2S,2'S,3R,3'E)-isomer 28 of 1 was also synthesized to further confirm the structure of 1. - Key Words: Ca(++)-ATPase activator / Ceramides / Marine natural products / Sphingosines / Symbioramide
Selective Isomerization of 1,2-Epoxyalkanes to Aldehydes with Lithium Dialkylamides
Yanagisawa, Akira,Yasue, Katsutaka,Yamamoto, Hisashi
, p. 2103 - 2104 (2007/10/02)
Reaction of a variety of 1,2-epoxyalkanes with 2.5 equiv. of bulky metal amide - lithium 2,2,6,6-tetramethylpiperidide - affords the corresponding aldehydes exclusively in high yields; this is the first example of base-promoted isomerization of monosubstituted epoxides to aldehydes.
