methyl 10-methoxycarbonyl-6,7,8,9,10-pentadeoxy-1-thio-β-L-galacto-decopyranoside | 408497-01-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 10-methoxycarbonyl-6,7,8,9,10-pentadeoxy-1-thio-β-L-galacto-decopyranoside
• 英文别名: methyl 6-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]hexanoate
• CAS: 408497-01-8
• 化学式: C₁₃H₂₄O₆S
• 分子量: 308.396
• InChiKey: VUVBFZFRKFJTGL-ZYJFBCHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 10-methoxycarbonyl-6,7,8,9,10-pentadeoxy-1-thio-β-L-galacto-decopyranoside 在 吡啶 、 iodonium(di-γ-collidine) perchlorate 、 4 A molecular sieve 、 sodium methylate 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 51.0h， 生成 10-methoxycarbonyl-6,7,8,9,10-pentadeoxy-α-L-galacto-decopyranosyl-(1->2)-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-2,3;4,6-di-O-isopropylidene-D-glucose dimethyl acetal
  参考文献：
  名称：

  SYNTHESIS AND APPLICATION OF SPACER-MODIFIED L-FUCOSE ANALOGUES1

  摘要：

  Starting from 6-O-tert-butyldimethylsilyl-2,3;4,5-di-O-isopropylidenealdehydo-D-galactose (1), the carbon backbone elongated GDP-L-fucose analogue 15 bearing a chromophore tag at the end of a spacer was synthesized. Additionally, the analogues of 3-L-fucosyllactose (29) and 2'-L-fucosyllactose (36), where the fucosyl moiety is marked by a five atom alkyl chain at C-5, were prepared as labeled oligosaccharides of human milk.

  DOI：

  10.1081/car-100108277
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-acetyl-10-methoxycarbonyl-6,7,8,9,10-pentadeoxy-1-thio-β-L-galacto-decopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以89%的产率得到methyl 10-methoxycarbonyl-6,7,8,9,10-pentadeoxy-1-thio-β-L-galacto-decopyranoside
  参考文献：
  名称：

  SYNTHESIS AND APPLICATION OF SPACER-MODIFIED L-FUCOSE ANALOGUES1

  摘要：

  Starting from 6-O-tert-butyldimethylsilyl-2,3;4,5-di-O-isopropylidenealdehydo-D-galactose (1), the carbon backbone elongated GDP-L-fucose analogue 15 bearing a chromophore tag at the end of a spacer was synthesized. Additionally, the analogues of 3-L-fucosyllactose (29) and 2'-L-fucosyllactose (36), where the fucosyl moiety is marked by a five atom alkyl chain at C-5, were prepared as labeled oligosaccharides of human milk.

  DOI：

  10.1081/car-100108277

文献信息

• SYNTHESIS AND APPLICATION OF SPACER-MODIFIED L-FUCOSE ANALOGUES1
  作者：Andrej-Jakob Ott、Meinolf Brackhagen、Anahit Davtyan、Birte Nolting、Hanna Boye、Astrid Schoknecht、Christian Vogel

  DOI：10.1081/car-100108277

  日期：——

  Starting from 6-O-tert-butyldimethylsilyl-2,3;4,5-di-O-isopropylidenealdehydo-D-galactose (1), the carbon backbone elongated GDP-L-fucose analogue 15 bearing a chromophore tag at the end of a spacer was synthesized. Additionally, the analogues of 3-L-fucosyllactose (29) and 2'-L-fucosyllactose (36), where the fucosyl moiety is marked by a five atom alkyl chain at C-5, were prepared as labeled oligosaccharides of human milk.