2975-92-0Relevant academic research and scientific papers
Facile enantiospecific synthesis of dihydroconduritols E and F
Prasad, Kavirayani R.,Pawar, Amit B.
experimental part, p. 3155 - 3159 (2009/04/06)
An enantiospecific synthesis of cyclohexane-1,2,3,4-tetrols was accomplished from L-(+)-tartaric acid. Pivotal steps in the synthetic sequence include zinc-mediated Boord-type fragmentation of an acetonide, ring-closing metathesis (RCM), and osmium-mediat
Dihydroxylation of polyenes using Narasaka's modification of the upjohn procedure
Gypser, Andreas,Michel, Dominique,Nirschl, David S.,Barry Sharpless
, p. 7322 - 7327 (2007/10/03)
Dihydroxylation of a variety of commercially available polyenes has been investigated using phenylboronic acid, .ZV-methylmorpholine Af-oxide (NMO), and osmium tetroxide in anhydrous solvent. The diastereoselectivity of multiple oxidation steps is in some cases affected by the in situ protection of the intermediate ene-diols as phenyboronic esters, affording polyols not available from the standard Upjohn dihydroxylation procedure. A convenient oxidative deprotection of the phenylboronic esters is also described.
Facile stereoselective syntheses of four of the six 1, 2, 3, 4-cyclohexanetetrols: Increasing the accessibility of cyclitols for probing the molecular recognition of saccharides
Huang,Cabell,Anslyn
, p. 2757 - 2764 (2007/10/02)
New and stereoselective syntheses of (1,2,3/4)-, (1,2/3,4)-, (1,4/2,3)-, and (1,2,4/3)-cyclohexanetetrols (1,2,3 and 4 respectively) are described. The known syn and anti 1,4-cyclohex-2-enediols 9 and 10 were used as starting materials. Diols 9 and 10 wer
Catalytic One-Pot Osmylation of Cyclohexadienes: Stereochemical and Conformational Studies of the Resulting Polyols
Tschamber, Theophile,Backenstrass, Frederique,Fritz, Hans,Streith, Jacques
, p. 1052 - 1060 (2007/10/02)
Catalytic double osmylation is described for a series of cyclohexadienes in acetone/H2O in the presence of the co-oxidant N-methylmorpholine N-oxide (NMO).The formation of polyols occurred stereospecifically with cyclohexadienes 3, 7, and 11a, leading thereby to tetrols 5a, and 9a and to allo-inositol (14a), respectively.To the contrary, trans-cyclohexadiene-diol 15a gave a mixture of the stereoisomeric inositols 18a (epi), 19a (neo), and 20a (chiro).High-field NMR let to clearcut conformational analyses of the polyhydroxylated derivatives.
Total Syntheses of (-)-Conduritol B ((-)-1L-Cyclohex-5-ene-1,3/2,4-tetrol) and of (+)-Conduritol F ((+)-1D-Cyclohex-5-ene-1,2,4/3-tetrol). Determination of the Absolute Configuration of (+)-Leucanthemitol
Drian, Claude Le,Vionnet, Jean-Paul,Vogel, Pierre
, p. 161 - 168 (2007/10/02)
The 'naked sugar' (+)-(1R,2R,4R)-2-endo-cyano-7-oxabicyclohept-5-en-2-exo-yl acetate ((+)-4) was converted (7 steps , 45percent overall) with high stereoselectivity into (-)-(4R,5S,6R)-4,5,6-tris(oxy)cyclohex-2-en-1-one (
A New and Stereospecific Synthesis of Cyclitols: (1,2,4/3)-, (1,2/3,4)-, and (1,3/2,4)-Cyclohexanetetrols
Akbulut, Nihat,Balci, Metin
, p. 3338 - 3342 (2007/10/02)
A new and stereospecific synthesis of (1,2,4/3)-, (1,2/3,4)-, and (1,3/2,4)-cyclohexanetetrols 3a, 4a, and 6a is described.Syn and anti epoxy endoperoxides 9 and 10 were synthesized by epoxidation of endoperoxide 8 with m-chloroperbenzoic acid.Catalytic r
A Facile Synthesis of Cyclitols from Cyclohexene
Hasegawa, Akira,Kobayshi, Toshiyuki,Kiso, Makoto
, p. 165 - 168 (2007/10/02)
A facile procedure to synthesize cyclitols from cyclohexene was examined. 1-O-Benzylcyclohex-2-enol (1-benzyloxycyclohexene-2) (I) was prepared from cyclohexene by bromination and successive treatment with sodium benzyloxide.Compound I was converted, by using the same procedure, into DL-trans-1,2-di-O-benzylcyclohex-3-enediol (IIIa), DL-trans- and meso-cis-1,4-di-O-benzylcyclohex-2-enediols (IIIb and IIIc).The main product (IIIa) was converted into dihydroconduritols (IXc and Xc) via the corresponding di-O-benzylcyclohexanetetrols.
