(-)-methyl 2-acetamido-4-O-acetyl-2,3-dideoxy-1-O-methyl-3-C-(3',4',5'-tri-O-acetyl-2',6'-anhydro-1',7'-dideoxy-α-L-glycero-D-glacto-heptitol-1'-C-yl)-β-D-galactopyranuronate | 408535-00-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-methyl 2-acetamido-4-O-acetyl-2,3-dideoxy-1-O-methyl-3-C-(3',4',5'-tri-O-acetyl-2',6'-anhydro-1',7'-dideoxy-α-L-glycero-D-glacto-heptitol-1'-C-yl)-β-D-galactopyranuronate
• 英文别名: methyl (2S,3R,4R,5R,6R)-5-acetamido-3-acetyloxy-6-methoxy-4-[[(2S,3R,4R,5R,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]methyl]oxane-2-carboxylate
• CAS: 408535-00-2
• 化学式: C₂₅H₃₇NO₁₄
• 分子量: 575.567
• InChiKey: LDULHNXKGRTZHQ-IXSVCBMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  188
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  (-)-methyl 2-acetamido-4-O-acetyl-2,3-dideoxy-1-O-methyl-3-C-(3',4',5'-tri-O-acetyl-2',6'-anhydro-1',7'-dideoxy-α-L-glycero-D-glacto-heptitol-1'-C-yl)-β-D-galactopyranuronate 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到(-)-methyl 2-acetamido-2,3-dideoxy-3-C-(2',6'-anhydro-1',7'-dideoxy-α-L-glycero-D-glacto-heptitol-1'-C-yl)-β-D-galactopyranoside
  参考文献：
  名称：

  SYNTHESIS OF THE C-DISACCHARIDE α-C(1→3)-L-FUCOPYRANOSIDE OF N-ACETYLGALACTOSAMINE1

  摘要：

  Radical C-glycosidation of racemic 5-exo-benzeneselenyl-6-endo-chloro-3-methylidene-7-oxabicyclo[2.2.1]heptan-2-one ((+/-)-2) with alpha -acetobromofucose (3) provided a mixture of alpha -C-fucosides that were reduced with NaBH4 to give two diastereomeric alcohols that were separated readily. One of them ((-)-6) was converted into (-)-methyl 2-acetamido-4-O-acetyl-2,3-dideoxy-3-C(3',4',5'-tri-O-acetyl-2',6'-anhydro- 1',7'-dideoxy-alpha -L-glycero-D-galacto-heptitol-1'-C-yl)-alpha -D-galactopyranuronate ((-)-11) and then into (-)-methyl 2-acetamido-2,3-dideoxy-3-C-(2',6'-anhydro- 1',7'-dideoxy-alpha -L-glycero-D-galacto-heptitol- 1'-C-yl)-beta -D-galactopyranoside a new alpha -C(1 -->3)-L-fucopyranoside of N-acetylgalactosamine. Its H-1 NMR data shows that this C-disaccharide (alpha -L-Fucp-(1 -->3)CH2-beta -D-GaINAc-OMe) adopts a major conformation in solution similar to that expected for the corresponding O-linked disaccharide, i.e., with antiperiplanar sigma (C-3',C-2') and sigma (C-1',C-3) bonds.

  DOI：

  10.1081/car-100108286
• 作为产物：
  描述：

  (-)-methyl 2-acetamido-4-O-acetyl-2,3-dideoxy-3-C-(3',4',5'-tri-O-acetyl-2',6'-anhydro-1',7'-dideoxy-α-L-glycero-D-galacto-heptitol-1'-C-yl)-α-D-galactopyranuronate 在 三氟化硼乙醚 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (-)-methyl 2-acetamido-4-O-acetyl-2,3-dideoxy-1-O-methyl-3-C-(3',4',5'-tri-O-acetyl-2',6'-anhydro-1',7'-dideoxy-α-L-glycero-D-glacto-heptitol-1'-C-yl)-β-D-galactopyranuronate
  参考文献：
  名称：

  SYNTHESIS OF THE C-DISACCHARIDE α-C(1→3)-L-FUCOPYRANOSIDE OF N-ACETYLGALACTOSAMINE1

  摘要：

  Radical C-glycosidation of racemic 5-exo-benzeneselenyl-6-endo-chloro-3-methylidene-7-oxabicyclo[2.2.1]heptan-2-one ((+/-)-2) with alpha -acetobromofucose (3) provided a mixture of alpha -C-fucosides that were reduced with NaBH4 to give two diastereomeric alcohols that were separated readily. One of them ((-)-6) was converted into (-)-methyl 2-acetamido-4-O-acetyl-2,3-dideoxy-3-C(3',4',5'-tri-O-acetyl-2',6'-anhydro- 1',7'-dideoxy-alpha -L-glycero-D-galacto-heptitol-1'-C-yl)-alpha -D-galactopyranuronate ((-)-11) and then into (-)-methyl 2-acetamido-2,3-dideoxy-3-C-(2',6'-anhydro- 1',7'-dideoxy-alpha -L-glycero-D-galacto-heptitol- 1'-C-yl)-beta -D-galactopyranoside a new alpha -C(1 -->3)-L-fucopyranoside of N-acetylgalactosamine. Its H-1 NMR data shows that this C-disaccharide (alpha -L-Fucp-(1 -->3)CH2-beta -D-GaINAc-OMe) adopts a major conformation in solution similar to that expected for the corresponding O-linked disaccharide, i.e., with antiperiplanar sigma (C-3',C-2') and sigma (C-1',C-3) bonds.

  DOI：

  10.1081/car-100108286