3-(benzyloxycarbonylamino)propyl 4-O-[6-O-benzyl-3,4-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranozyl)-β-D-galactopyranosyl]-6-O-t-butyldiphenylsilyl-2-deoxy-2-phthalimido-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranozyl)-β-D-glucopyranoside | 1334630-90-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(benzyloxycarbonylamino)propyl 4-O-[6-O-benzyl-3,4-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranozyl)-β-D-galactopyranosyl]-6-O-t-butyldiphenylsilyl-2-deoxy-2-phthalimido-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranozyl)-β-D-glucopyranoside
• 英文别名: N-[3-[(2R,3R,4R,5S,6R)-5-[[(3aS,4R,6S,7R,7aS)-2,2-dimethyl-7-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-4-(phenylmethoxymethyl)-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-(1,3-dioxoisoindol-2-yl)-4-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxyoxan-2-yl]oxypropyl]-1-phenylmethoxymethanimidic acid
• CAS: 1334630-90-8
• 化学式: C₁₁₁H₁₂₂N₂O₂₂Si
• 分子量: 1864.28
• InChiKey: RPGWPPLVVNPXLQ-VJKVFLONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.91
• 重原子数：
  136
• 可旋转键数：
  43
• 环数：
  17.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  242
• 氢给体数：
  1
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  3-(benzyloxycarbonylamino)propyl 4-O-[6-O-benzyl-3,4-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranozyl)-β-D-galactopyranosyl]-6-O-t-butyldiphenylsilyl-2-deoxy-2-phthalimido-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranozyl)-β-D-glucopyranoside 在 水 、 溶剂黄146 作用下， 反应 2.0h， 以85%的产率得到3-(benzyloxycarbonylamino)propyl 4-O-[6-O-benzyl-2-O-(2,3,4-tri-O-benzyl-α-Lfucopyranosyl)-β-D-galactopyranosyl]-6-O-t-butyldiphenylsilyl-2-deoxy-2-phthalimido-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  建立血型与埃尔托霍乱严重程度之间关系的结构基础

  摘要：

  众所周知，O 型血的人比 A 型或 B 型血的人更容易受到 El Tor 霍乱的影响。 微量热法和核磁共振光谱用于评估霍乱毒素和大肠杆菌的 B 亚基的能力热不稳定毒素与选定的血型寡糖结合。

  DOI：

  10.1002/anie.201109068
• 作为产物：
  描述：

  3-(benzyloxycarbonylamino)propyl 4-O-(6-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-6-O-t-butyldiphenylsilyl-2-deoxy-2-phthalimido-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranozyl)-β-D-glucopyranoside 、 ethyl 2,3,4-tri-O-benzyl-1-thio-α-L-fucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以71%的产率得到3-(benzyloxycarbonylamino)propyl 4-O-[6-O-benzyl-3,4-O-isopropylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranozyl)-β-D-galactopyranosyl]-6-O-t-butyldiphenylsilyl-2-deoxy-2-phthalimido-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranozyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Studies on the synthesis of Lewis-y oligosaccharides

  摘要：

  Lewis-y histo-blood group oligosaccharides are tumour-associated antigens prevalent in several different types of cancer, and they may also be secondary ligands for bacterial toxins from Escherichia coli and Vibrio cholerae. The key step in the synthesis of these sterically congested oligosaccharides involves difucosylation of partially protected lactosamine derivatives. Existing methods require either prolonged reaction times or elaborate glycosyl donors to ensure high stereoselectivity. Herein we report an optimised procedure for using a simple thioglycoside donor that leads to the desired products in high yield and excellent stereoselectivity. It is found that initial glycosylation of the 3'-hydroxy group of lactosamine derivatives in dichloromethane solution can inhibit subsequent glycosylation at the 2-position; however, reaction in toluene solution leads to Lewis-y oligosaccharides in high yield. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.07.002

文献信息

• Studies on the synthesis of Lewis-y oligosaccharides
  作者：Pintu K. Mandal、W. Bruce Turnbull

  DOI：10.1016/j.carres.2011.07.002

  日期：2011.10

  Lewis-y histo-blood group oligosaccharides are tumour-associated antigens prevalent in several different types of cancer, and they may also be secondary ligands for bacterial toxins from Escherichia coli and Vibrio cholerae. The key step in the synthesis of these sterically congested oligosaccharides involves difucosylation of partially protected lactosamine derivatives. Existing methods require either prolonged reaction times or elaborate glycosyl donors to ensure high stereoselectivity. Herein we report an optimised procedure for using a simple thioglycoside donor that leads to the desired products in high yield and excellent stereoselectivity. It is found that initial glycosylation of the 3'-hydroxy group of lactosamine derivatives in dichloromethane solution can inhibit subsequent glycosylation at the 2-position; however, reaction in toluene solution leads to Lewis-y oligosaccharides in high yield. (C) 2011 Elsevier Ltd. All rights reserved.
• Towards a Structural Basis for the Relationship Between Blood Group and the Severity of El Tor Cholera
  作者：Pintu K. Mandal、Thomas R. Branson、Edward D. Hayes、James F. Ross、Jose A. Gavín、Antonio H. Daranas、W. Bruce Turnbull

  DOI：10.1002/anie.201109068

  日期：2012.5.21

  It has long been known that people with blood group O are more severely affected by El Tor cholera than those with blood groups A or B. Microcalorimetry and NMR spectroscopy are used to evaluate the ability of the B‐subunits of cholera toxin and E. coli heat‐labile toxin to bind to selected blood group oligosaccharides.

  众所周知，O 型血的人比 A 型或 B 型血的人更容易受到 El Tor 霍乱的影响。 微量热法和核磁共振光谱用于评估霍乱毒素和大肠杆菌的 B 亚基的能力热不稳定毒素与选定的血型寡糖结合。