4-Bromo-benzoic acid (2S,3S,4S,5R,6R)-3,5-dihydroxy-2-methoxy-6-[(E)-3-(4-methoxy-phenyl)-acryloyloxymethyl]-tetrahydro-pyran-4-yl ester | 116187-70-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Bromo-benzoic acid (2S,3S,4S,5R,6R)-3,5-dihydroxy-2-methoxy-6-[(E)-3-(4-methoxy-phenyl)-acryloyloxymethyl]-tetrahydro-pyran-4-yl ester
• CAS: 116187-70-3
• 化学式: C₂₄H₂₅BrO₉
• 分子量: 537.361
• InChiKey: RJGDJQRAKPWPLI-AKVCJDDMSA-N

反应信息

• 作为反应物：
  描述：

  4-Bromo-benzoic acid (2S,3S,4S,5R,6R)-3,5-dihydroxy-2-methoxy-6-[(E)-3-(4-methoxy-phenyl)-acryloyloxymethyl]-tetrahydro-pyran-4-yl ester 、 乙酸酐 在 4-二甲氨基吡啶 吡啶 作用下， 生成 4-Bromo-benzoic acid (2S,3S,4S,5R,6R)-3,5-diacetoxy-2-methoxy-6-[(E)-3-(4-methoxy-phenyl)-acryloyloxymethyl]-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Oligosaccharide microanalysis by C.D. spectroscopy. Reference curves for d-mannose derivatives

  摘要：

  This study completes the spectroscopic basis for a novel oligosaccharide microanalytical method, wherein a derivatization sequence provides monosaccharide subunits bearing two types of exciton-coupling chromophore groups ("bichromophoric") for circular dichroic spectroscopy, namely 4-bromobenzoate (lambda max 245 nm) and 4-methoxycinnamate (lambda max 311 nm). The 24 possible derivatives of methyl alpha-D-mannopyranoside bearing two chromophore and two acetate groups have been prepared and their c.d. spectra recorded. These spectra have been used to calculate the c.d. curves of the 14 possible tetrachromophic derivatives according to the pairwise additivity rule. The accuracy of these calculations has been demonstrated for six representative derivatives. The c.d. curves obtained here, together with curves of the corresponding D-glucose and D-galactose derivatives, comprise a set of 42 unique and distinctive spectra which can be utilized to identify sugars and their linkage patterns, and thus represent the basis for an alternative to methylation analysis which does not rely upon synthetic standards.

  DOI：

  10.1016/0008-6215(90)84126-f
• 作为产物：
  描述：

  (E)-3-(4-Methoxy-phenyl)-acrylic acid (2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester 、 4-溴苯甲酰氯 在 4-二甲氨基吡啶 吡啶 作用下， 生成 4-Bromo-benzoic acid (2S,3S,4S,5R,6R)-3,5-dihydroxy-2-methoxy-6-[(E)-3-(4-methoxy-phenyl)-acryloyloxymethyl]-tetrahydro-pyran-4-yl ester 、 4-Bromo-benzoic acid (2R,3S,4R,5S,6S)-4,5-dihydroxy-6-methoxy-2-[(E)-3-(4-methoxy-phenyl)-acryloyloxymethyl]-tetrahydro-pyran-3-yl ester 、 4-Bromo-benzoic acid (2S,3S,4S,5S,6R)-4,5-dihydroxy-2-methoxy-6-[(E)-3-(4-methoxy-phenyl)-acryloyloxymethyl]-tetrahydro-pyran-3-yl ester 、 [(2R,3R,4S,5S,6S)-4,5-bis[(4-bromobenzoyl)oxy]-6-methoxy-2-[[(E)-3-(4-methoxyphenyl)prop-2-enoyl]oxymethyl]oxan-3-yl] 4-bromobenzoate
  参考文献：
  名称：

  Oligosaccharide microanalysis by C.D. spectroscopy. Reference curves for d-mannose derivatives

  摘要：

  This study completes the spectroscopic basis for a novel oligosaccharide microanalytical method, wherein a derivatization sequence provides monosaccharide subunits bearing two types of exciton-coupling chromophore groups ("bichromophoric") for circular dichroic spectroscopy, namely 4-bromobenzoate (lambda max 245 nm) and 4-methoxycinnamate (lambda max 311 nm). The 24 possible derivatives of methyl alpha-D-mannopyranoside bearing two chromophore and two acetate groups have been prepared and their c.d. spectra recorded. These spectra have been used to calculate the c.d. curves of the 14 possible tetrachromophic derivatives according to the pairwise additivity rule. The accuracy of these calculations has been demonstrated for six representative derivatives. The c.d. curves obtained here, together with curves of the corresponding D-glucose and D-galactose derivatives, comprise a set of 42 unique and distinctive spectra which can be utilized to identify sugars and their linkage patterns, and thus represent the basis for an alternative to methylation analysis which does not rely upon synthetic standards.

  DOI：

  10.1016/0008-6215(90)84126-f