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Physiological and Biophysical Properties of Male Germ Cell Sulfogalactosylglycerolipid
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De Vriese S. AOCS Press: Champaign, IL
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Tanphaichitr, N.; Bou Khalil, M.; Weerachatyanukul, W.; Kates, M.; Xu, H.; Carmona, E.; Attar, M.; Carrier, D. Physiological and Biophysical Properties of Male Germ Cell Sulfogalactosylglycerolipid. In Lipid Metabolism and Male Fertility; De Vriese, S., Ed.; AOCS Press: Champaign, IL, 2003.
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Lipid Metabolism and Male Fertility
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For evidence that in mouse testis, besides the major molecule 1a, some (C16:0-alkyl-C14:0-acyl), (C14:0-alkyl-C16:0-acyl), and (C17:0-alkyl-C16:0-acyl) species are expressed during testicular maturation, see
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For evidence that in mouse testis, besides the major molecule 1a, some (C16:0-alkyl-C14:0-acyl), (C14:0-alkyl-C16:0-acyl), and (C17:0-alkyl-C16:0-acyl) species are expressed during testicular maturation, see: Goto-Inoue, N.; Hayasaka, T.; Zaima, N.; Setou, M. Glycobiology 2009, 19, 950-957
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84855623681
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1′,2′ = 8.0 Hz
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1′,2′ = 8.0 Hz.
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0030600180
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84855623017
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Zemplèn transesterification, performed with 1 molar eq. of sodium methoxide and stopped after 48 h, avoided TBS cleavage; in these conditions, 15% of the byproduct benzylated at position 4 and 6 but retaining the benzoate at position 2 was recovered after flash chromatography
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Zemplèn transesterification, performed with 1 molar eq. of sodium methoxide and stopped after 48 h, avoided TBS cleavage; in these conditions, 15% of the byproduct benzylated at position 4 and 6 but retaining the benzoate at position 2 was recovered after flash chromatography.
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0000139852
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Carretero, J.C.1
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84855617456
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Preliminary attempts on tetradecanal or cyclohexanone models afforded the corresponding α,β-unsaturated sulfonates in 60-70% yield
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Preliminary attempts on tetradecanal or cyclohexanone models afforded the corresponding α,β-unsaturated sulfonates in 60-70% yield.
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36
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77955158696
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For our purposes the very difficult separation of sulfonates 2a and 2b was not required as both isomers had to stereoselectively converge to a single reduction product
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For our purposes the very difficult separation of sulfonates 2a and 2b was not required as both isomers had to stereoselectively converge to a single reduction product.
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84855637456
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E/Z ratio was 2:1 according to integration of the olefinic proton (δ 6.78 ppm for E -isomer and δ 6.68 ppm for Z -isomer)
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E/Z ratio was 2:1 according to integration of the olefinic proton (δ 6.78 ppm for E -isomer and δ 6.68 ppm for Z -isomer).
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38
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77955133089
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Attempts to reduce compounds 2a,b by catalytic hydrogenation in the presence of Pt/C resulted in an incomplete reaction, and sodium borohydride showed stereoselectivity in favour of the gulo -isomer. Moreover, a difference of reactivity between 2a and 2b was observed in the hydrogenation reaction where TLC analysis showed a faster reduction of compound 2a with respect to compound 2b
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Attempts to reduce compounds 2a,b by catalytic hydrogenation in the presence of Pt/C resulted in an incomplete reaction, and sodium borohydride showed stereoselectivity in favour of the gulo -isomer. Moreover, a difference of reactivity between 2a and 2b was observed in the hydrogenation reaction where TLC analysis showed a faster reduction of compound 2a with respect to compound 2b.
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