109010-30-2Relevant academic research and scientific papers
Chemoenzymatic Synthesis of Advanced Intermediates for Formal Total Syntheses of Tetrodotoxin
Baidilov, Daler,Rycek, Lukas,Trant, John F.,Froese, Jordan,Murphy, Brennan,Hudlicky, Tomas
supporting information, p. 10994 - 10998 (2018/06/04)
Advanced intermediates for the syntheses of tetrodotoxin reported by the groups of Fukuyama, Alonso, and Sato were prepared. Key steps include the toluene dioxygenase mediated dihydroxylation of either iodobenzene or benzyl acetate. The resulting diene diols were transformed into Fukuyama's intermediate in six steps, into Alonso's intermediate in nine steps, and into Sato's intermediate in ten steps.
Total synthesis of (-)-tetrodotoxin from D-glucose: A new route to multi-functionalized cyclitol employing the ferrier(II) reaction toward (-)-tetrodotoxin
Akai, Shoji,Seki, Hidehito,Sugita, Naoki,Kogure, Tomokazu,Nishizawa, Naoki,Suzuki, Katsuhiko,Nakamura, Yutaka,Kajihara, Yasuhiro,Yoshimura, Juji,Sato, Ken-Ichi
experimental part, p. 279 - 287 (2010/06/17)
Total synthesis of (-)-tetrodotoxin (TTX) from D-glucose is described. As a critical transformation step for synthesizing TTX, a key multi-functionalized cyclitol was prepared from D-glucose employing the Ferrier(II) reaction. Stereospecific introduction of three functionalized branched chains were achieved via Peterson olefination and spiro α-chloroepoxidation of the corresponding carbonyl derivatives.
Highly functionalized, enantiomerically pure furo[x,y-c]pyrans via alkylidenecarbenes derived from sugar templates: synthesis and mechanism study via computational chemistry
Nguyen Van Nhien, Albert,Cordonnier, Romaric,Le Bas, Marie-Delphine,Delacroix, Sébastien,Soriano, Elena,Marco-Contelles, José,Postel, Denis
experimental part, p. 9378 - 9394 (2009/12/28)
The new method for the generation of alkylidenecarbenes based on the reaction of trimethylsilylazide/Bu2SnO with α-cyanomesylates has been applied to readily available sugar derivatives for the synthesis of highly functionalized, enantiomerical
The synthesis of carbohydrate α-amino acids utilizing the Corey-Link reaction
Scaffidi, Adrian,Skelton, Brian W.,Stick, Robert V.,White, Allan H.
, p. 723 - 732 (2007/10/03)
Various carbohydrate ketones (uloses) have been treated with chloroform under strongly basic conditions to yield trichloromethyl tertiary alcohols. These alcohols, when subjected to the conditions of the modified Corey-Link reaction (sodium azide and 1,8-
An alternative synthesis of some carbohydrate α-amino acids
Forman, Grant S.,Scaffidi, Adrian,Stick, Robert V.
, p. 25 - 28 (2007/10/03)
Several carbohydrate ketones have been converted into their trichloromethyl-branched tertiary alcohols. A subsequent treatment of these alcohols under Corey-Link conditions (base, sodium azide, methanol) has given rise to α-azido esters, transformable int
Studies of the stereoselective reduction of ketosugar (hexosulose)
Chang, Cheng-Wei Tom,Hui, Yu,Elchert, Bryan
, p. 7019 - 7023 (2007/10/03)
The results from the studies of the stereoselective reduction of ketosugar (hexosulose) were reported. Combining our results and those reported in the literature, we summarize the factors in controlling the stereoselective reduction of ketosugars. These findings are valuable in the synthesis of various carbohydrate derivatives.
Synthesis of Methyl 2-O-Benzyl-6-deoxy-3-C-methyl-α-D-mannopyranoside and Methyl α-D-Evalopyranoside
Zagar, Cyrill,Scharf, Hans-Dieter
, p. 693 - 697 (2007/10/02)
Methyl 2-O-benzyl-6-deoxy-3-C-methyl-α-D-mannopyranoside (2) was synthesized in ten steps by starting from the readily available methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside (3).The key step was the stereoselective cis-hydroxylation (cat. osmiu
Enolates of carbohydrates, 5. Syntheses of axially methyl-branched pyranosiduloses
Klemer, Almuth,Klaffke, Werner
, p. 759 - 764 (2007/10/02)
The α-C-methylated carbohydrates 3 and 5 are available from the benzoyl- and benzylidene protected 2- and 3-uloses 1a, 2, and 4 by reaction with potassium tert-butoxide/methyl iodide in N,N-dimethylformamide.Under pthe same conditions the 2-O-benzyl-3-ulose 1b yields the enol ether 6a, and the enolone 8 is obtained from the 2-O-benzoyl-3-ulose 7.
SYNTHETIC RECEPTOR ANALOGUES: PREPARATION OF THE 3-O-METHYL, 3-C-METHYL, AND 3-DEOXY DERIVATIVES OF METHYL 4-O-α-D-GALACTOPYRANOSYL-β-D-GALACTOPYRANOSIDE (METHYL β-D-GALABIOSIDE)
Kihlberg, Jan,Frejd, Torbjoern,Jansson, Karl,Magnusson, Goeran
, p. 113 - 130 (2007/10/02)
Methyl β-D-galactopyranoside was transformed into methyl 2-O-benzyl- (5, 24percent) and 2-O-benzyloxymethyl-4,6-O-benzylidene-β-D-galactopyranoside (8, 60percent) in two and four steps respectively.Compounds 5 and 8 were then transformed into the correspo
