(-)-(1S,2R,3S,4R,5R,6R)-5-exo-benzeneselenyl-6-endo-chloro-3-endo-[(3',4',5'-tri-O-acetyl-2',6'-anhydro-1',7'-dideoxy-α-L-glycero-D-galacto-heptitol-1'-C-yl)]-7-oxabicyclo[2.2.1]hept-2-endo-ol | 408534-93-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-(1S,2R,3S,4R,5R,6R)-5-exo-benzeneselenyl-6-endo-chloro-3-endo-[(3',4',5'-tri-O-acetyl-2',6'-anhydro-1',7'-dideoxy-α-L-glycero-D-galacto-heptitol-1'-C-yl)]-7-oxabicyclo[2.2.1]hept-2-endo-ol
• 英文别名: [(2S,3R,4R,5R,6S)-4,5-diacetyloxy-6-[[(1R,2S,3R,4S,5R,6R)-5-chloro-3-hydroxy-6-phenylselanyl-7-oxabicyclo[2.2.1]heptan-2-yl]methyl]-2-methyloxan-3-yl] acetate
• CAS: 408534-93-0
• 化学式: C₂₅H₃₁ClO₉Se
• 分子量: 589.929
• InChiKey: DXUURPWJXGBHFP-ZPFHBNMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.14
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (-)-(1S,2R,3S,4R,5R,6R)-5-exo-benzeneselenyl-6-endo-chloro-3-endo-[(3',4',5'-tri-O-acetyl-2',6'-anhydro-1',7'-dideoxy-α-L-glycero-D-galacto-heptitol-1'-C-yl)]-7-oxabicyclo[2.2.1]hept-2-endo-ol 在 吡啶 、 4-二甲氨基吡啶 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 (-)-(1S,2R,3S,4R)-6-chloro-3-endo-[(3',4',5'-tri-O-acetyl-2',6'-anhydro-1',7'-dideoxy-α-L-glycero-D-galacto-heptitol-1'-C-yl)]-7-oxabicyclo[2.2.1]hept-5-en-2-endo-yl acetate
  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：

  5-exo-benzeneselenyl-6-endo-chloro-3-endo-[(3',4',5'-tri-O-acetyl-2',6'-anhydro-1',7'-dideoxy-α-L-glycero-D-galacto-heptitol-1'-C-yl)]-7-oxabicyclo[2.2.1]hept-2-one 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.08h， 以40%的产率得到(-)-(1S,2R,3S,4R,5R,6R)-5-exo-benzeneselenyl-6-endo-chloro-3-endo-[(3',4',5'-tri-O-acetyl-2',6'-anhydro-1',7'-dideoxy-α-L-glycero-D-galacto-heptitol-1'-C-yl)]-7-oxabicyclo[2.2.1]hept-2-endo-ol
  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