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 | 1334631-10-5

• 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-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: benzyl N-[3-[(2R,3R,4R,5S,6R)-5-[[(3aS,4R,6S,7R,7aR)-7-hydroxy-2,2-dimethyl-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]carbamate
• CAS: 1334631-10-5
• 化学式: C₈₄H₉₄N₂O₁₈Si
• 分子量: 1447.76
• InChiKey: DUHOYENXIHEKAH-LUJSOLQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.38
• 重原子数：
  105
• 可旋转键数：
  32
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  216
• 氢给体数：
  2
• 氢受体数：
  18

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  、 2,2-二甲氧基丙烷 在 camphor-10-sulfonic acid 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以1.6 g的产率得到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
  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.