3-benzyloxycarbonylamino-1-propyl 6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranoside | 347391-77-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzyloxycarbonylamino-1-propyl 6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• 英文别名: 3-(benzyloxycarbonylamino)propyl 6-O-t-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranoside；benzyl N-[3-[(2R,3R,4R,5S,6R)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-(1,3-dioxoisoindol-2-yl)-4,5-dihydroxyoxan-2-yl]oxypropyl]carbamate
• CAS: 347391-77-9
• 化学式: C₄₁H₄₆N₂O₉Si
• 分子量: 738.91
• InChiKey: SVSSMPMMNVGZSD-QCALRNTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  53
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  144
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-benzyloxycarbonylamino-1-propyl 6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 camphor-10-sulfonic acid 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 3-(benzyloxycarbonylamino)propyl 4-O-(6-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-6-O-t-butyldiphenylsilyl-2-deoxy-2-phthalimido-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-脱氧-2-苯二酰亚胺-1,3,4,6-四-氧-乙酰-β-D-吡喃葡萄糖 在 咪唑 、 四氟硼酸-二乙醚络合物 、 氢溴酸 、 sodium methylate 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 乙酸酐 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 26.0h， 生成 3-benzyloxycarbonylamino-1-propyl 6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Practical syntheses of B disaccharide and linear B type 2 trisaccharide—non-primate epitope markers recognized by human anti-α-Gal antibodies causing hyperacute rejection of xenotransplants

  摘要：

  Synthetic protocols are presented for the elaboration of Gal alpha1 --> 3GalOR and Gal alpha1 --> 3Gal beta1 --> 4GlcNAcOR di- and trisaccharides that use a common Gal donor/acceptor unit, and are potentially adaptable to scale-up. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00196-x

文献信息

• Practical syntheses of B disaccharide and linear B type 2 trisaccharide—non-primate epitope markers recognized by human anti-α-Gal antibodies causing hyperacute rejection of xenotransplants
  作者：Stephen Hanessian、Oscar M Saavedra、Vincent Mascitti、Wolfgang Marterer、Reinhold Oehrlein、Ching-Pong Mak

  DOI：10.1016/s0040-4020(01)00196-x

  日期：2001.4

  Synthetic protocols are presented for the elaboration of Gal alpha1 --> 3GalOR and Gal alpha1 --> 3Gal beta1 --> 4GlcNAcOR di- and trisaccharides that use a common Gal donor/acceptor unit, and are potentially adaptable to scale-up. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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.