benzyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-[2,3,4-tri-O-benzyl-6,7,8,9,10-pentadeoxy-α-L-galacto-decopyranosyl-(1->3)]-2,6-di-O-benzyl-β-D-glucopyranoside | 408497-06-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-[2,3,4-tri-O-benzyl-6,7,8,9,10-pentadeoxy-α-L-galacto-decopyranosyl-(1->3)]-2,6-di-O-benzyl-β-D-glucopyranoside
• 英文别名: (3aS,4R,6S,7R,7aS)-2,2-dimethyl-6-[(2R,3R,4S,5R,6R)-4-[(2S,3S,4R,5R,6S)-6-pentyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-5,6-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-7-phenylmethoxy-4-(phenylmethoxymethyl)-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran
• CAS: 408497-06-3
• 化学式: C₈₁H₉₂O₁₅
• 分子量: 1305.61
• InChiKey: QFVMILPQTSILSJ-MBLCAFDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.4
• 重原子数：
  96
• 可旋转键数：
  34
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  138
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  benzyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-[2,3,4-tri-O-benzyl-6,7,8,9,10-pentadeoxy-α-L-galacto-decopyranosyl-(1->3)]-2,6-di-O-benzyl-β-D-glucopyranoside 在 溶剂黄146 作用下， 以 水 为溶剂， 以60%的产率得到benzyl 2,6-di-O-benzyl-β-D-galactopyranosyl-(1->4)-[2,3,4-tri-O-benzyl-6,7,8,9,10-pentadeoxy-α-L-galacto-decopyranosyl-(1->3)]-2,6-di-O-benzyl-β-D-glucopyranoside
  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：

  1,2,3,4-tetra-O-acetyl-6,7,8,9,10-pentadeoxy-L-galacto-decopyranose 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 sodium methylate 、 sodium hydride 、 DMTST 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 34.0h， 生成 benzyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-[2,3,4-tri-O-benzyl-6,7,8,9,10-pentadeoxy-α-L-galacto-decopyranosyl-(1->3)]-2,6-di-O-benzyl-β-D-glucopyranoside
  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.