Zur Chemie des Benzolglykols, IV. Darstellung von <i>cis</i>‐Benzolglykol, stereoisomeren Mucondialdehyden und Kondurit‐F

Nakajima, Minoru; Tomida, Ichiro; Takei, Sankichi

doi:10.1002/cber.19590920119

Cited by 63 publications

(12 citation statements)

References 7 publications

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“…According to Nukujimu et ul., catalytic osmylation of l l a in the presence of AgC10, gave mostly phenol (48%) and small amounts of conduritol E (4% 12b after acetylation) [7]. Furthermore, when bis-acetate l l b was hydroxylated with KMnO, in neutral medium, these authors isolated 12b only (61 Yo) [8], whereas catalytic osmylation of l l a in the presence of 1 equiv. of NMO led to a mixture 12b/13b after acetylation (see below).…”

Section: <->mentioning

confidence: 98%

Catalytic One‐Pot Osmylation of Cyclohexadienes: Stereochemical and conformational studies of the resulting polyols

Tschamber

Backenstrass

Fritz

et al. 1992

Helvetica Chimica Acta

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' ) Physikalische Abteilung, Cibu-tieigy A t i , CH4002 Base1 (8.1V.92) Catalytic double osmylation is described for a series of cyclohexadienes in acetone/H,O in the presence of the co-oxidant ~'-methylmorpholine N-oxide (NMO). The formation of polyols occurred stereospecifically with cyclohexadienes 3,7, and l l a , leading thereby to tetrols 5a, and 9a and to alio-inositol(14a), respectively. To the contrary, trans-cyclohexadiene-diol 15a gave a mixture of the stereoisomeric inositols 18a (epi), 19a (nro), and 20a (chiro). High-field NMR let to clearcut conformational analyses of the polyhydroxylated derivatives.Introduction. ~ In a preliminary communication, we described the one-pot double catalytic osmylation of dihydropyridine 1 which led stereospecifically to the aminodideoxyaltrose derivative 2 [ 11. The stereospecific 'cisltranslcisltrans' outcome of this multistep reaction -which led in good yield to 5 asymmetric centres ~ is most probably due to minimization of steric interactions during each osmylation step. Due to the strong anomeric effect, which is more pronounced in piperidinoses than in pyranoses, compound 2 occurred exclusively in the chair conformation [ 11.

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Section: <->mentioning

confidence: 98%

Catalytic One‐Pot Osmylation of Cyclohexadienes: Stereochemical and conformational studies of the resulting polyols

Tschamber

Backenstrass

Fritz

et al. 1992

Helvetica Chimica Acta

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“…This should stimulate the development of new syntheses of optically pure conduritols. Whereas racemic conduritol C ((&)-3) has been derived from epi-inosito1 [23] and from cyclohexa-3,5-diene-1,2-diol [24], we report here the first total synthesis of optically pure (-)-conduritol C ((-)-3).…”

Section: Ho Oh Oh Oh Homentioning

confidence: 98%

Synthesis of (−)‐Conduritol C (1L‐Cyclohex‐5‐ene‐1,2,3/4‐tetrol)

Drian

Vieira

Vogel

1989

Helvetica Chimica Acta

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“…[14] for the p-nitrophenyl com pound; for fluorometric assays it was necessary to recrystallize both materials from ethanol repeatedly, to lower blank readings. Synthesis of l,5-dideoxy-l,5-imino-D-mannitol was performed as described pre viously [15], l,2-Anhydro(l,2,3,5,6/4)cyclohexane hexol (II) was prepared as follows: conduritol F [16] (100 mg) was stirred with m-chloroperbenzoic acid (400 mg) in acetic acid:methanol 1:1 (4 ml). Benzoic acids were removed by dilution with water and re peated extraction with ether, the aqueous phase was concentrated to dryness and the residue was purified by preparative thin layer chromatography on silica gel in ethanokethyl acetate:water 2:4:1 (zones detected by spraying control strips with 0.5% KMn04).…”

Section: Methodsmentioning

confidence: 99%

Goat Liver ß-Mannosidases: Molecular Properties, Inhibition and Inactivation of the Lysosomal and Nonlysosomal Forms

Kt¹,

Ra²,

Legler³

et al. 1985

Enzyme

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The two caprine hepatic ß-mannosidases have been partially purified and their properties have been compared. The lysosomal ß-mannosidase A had an apparent molecular weight of 127,000 ± 10,000 and an isoelectric point of pH 6-7. Its activity was unaffected by incubation with Triton X-100 (0.1 %) and cysteine (20 mM) and it hydrolyzed the presumed natural substrates, Man(ß1-4)GlcNAc and Man(ß1—4)GlcNaC(ß1-4)GlcNAc. The nonlysosomal ß-mannosidase B had an apparent molecular weight of 43,000 ± 2,000 and an isoelectric point of pH 5.5. ß-Mannosidase B was activated by Triton X-100 (0.1 %) and was inhibited by cysteine (20 mM). Hydrolysis of Man(ß1-4)GlcNAc, but not of Man(ß1- 4)GlcNAc(ß1-4)GlcNAc, followed incubation with ß-mannosidase B. 1,5-Dideoxy-1,5-imino- D-mannitol did not inhibit the A enzyme and only feebly (K(i) = 0.3 mM) inhibited the B enzyme; ß-D-mannopyranosylmethyl p-nitrophenyl triazene did not inactivate either enzyme but 1,2-anhydro-1,2,3,5,6/4-cyclohexane hexol inactivated the B enzyme only. The radical mechanistic differences between the two enzymes argue against their having the same genetic origin.

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Zur Chemie des Benzolglykols, IV. Darstellung von cis‐Benzolglykol, stereoisomeren Mucondialdehyden und Kondurit‐F

Cited by 63 publications

References 7 publications

Catalytic One‐Pot Osmylation of Cyclohexadienes: Stereochemical and conformational studies of the resulting polyols

Catalytic One‐Pot Osmylation of Cyclohexadienes: Stereochemical and conformational studies of the resulting polyols

Synthesis of (−)‐Conduritol C (1L‐Cyclohex‐5‐ene‐1,2,3/4‐tetrol)

Goat Liver ß-Mannosidases: Molecular Properties, Inhibition and Inactivation of the Lysosomal and Nonlysosomal Forms

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