1-O-[[(2R,3S,4R,5R,6S)-5-acetamido-3-hydroxy-6-methoxy-4-phenylmethoxyoxan-2-yl]methyl] 4-O-[(2S,3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-phenylsulfanyloxan-3-yl] butanedioate | 191216-63-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 1-O-[[(2R,3S,4R,5R,6S)-5-acetamido-3-hydroxy-6-methoxy-4-phenylmethoxyoxan-2-yl]methyl] 4-O-[(2S,3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-phenylsulfanyloxan-3-yl] butanedioate
• CAS: 191216-63-4
• 化学式: C₅₃H₅₉NO₁₃S
• 分子量: 950.116
• InChiKey: BHXPTIFKYZPUEM-KOCQSTLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  68
• 可旋转键数：
  25
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  192
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  1-O-[[(2R,3S,4R,5R,6S)-5-acetamido-3-hydroxy-6-methoxy-4-phenylmethoxyoxan-2-yl]methyl] 4-O-[(2S,3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-phenylsulfanyloxan-3-yl] butanedioate 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以29%的产率得到N-[(1S,3R,5R,6R,7S,8R,16R,18S,19R,20R)-18-methoxy-10,13-dioxo-6,7,20-tris(phenylmethoxy)-5-(phenylmethoxymethyl)-2,4,9,14,17-pentaoxatricyclo[14.4.0.03,8]icosan-19-yl]acetamide
  参考文献：
  名称：

  Intramolecular glycosylation of prearranged glycosides part 5. α-(1→4)-Selective glucosylation of glucosides and glucosamines

  摘要：

  The intramolecular (1 -->4) glucosylation of partially protected alkyl glucosides and glucosamines with phenyl 1-thioglucoside that is preconnected via its position 2 by a succinyl spacer to positions 3 of the glucosyl acceptor affords the alpha-linked disaccharides. The anomeric selectivity depends on the stereochemistry of the donor-acceptor-interaction and is not governed by neighboring group participation. In contrast, connecting the glucosyl donor by the succinyl bridge to position 6 of the glucosamine acceptor results in an alpha/beta-mixture of the corresponding disaccharides upon intramolecular glycosylation. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00729-6
• 作为产物：
  描述：

  Phenyl 3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 为溶剂， 反应 60.0h， 生成 1-O-[[(2R,3S,4R,5R,6S)-5-acetamido-3-hydroxy-6-methoxy-4-phenylmethoxyoxan-2-yl]methyl] 4-O-[(2S,3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-phenylsulfanyloxan-3-yl] butanedioate
  参考文献：
  名称：

  Intramolecular glycosylation of prearranged glycosides part 5. α-(1→4)-Selective glucosylation of glucosides and glucosamines

  摘要：

  The intramolecular (1 -->4) glucosylation of partially protected alkyl glucosides and glucosamines with phenyl 1-thioglucoside that is preconnected via its position 2 by a succinyl spacer to positions 3 of the glucosyl acceptor affords the alpha-linked disaccharides. The anomeric selectivity depends on the stereochemistry of the donor-acceptor-interaction and is not governed by neighboring group participation. In contrast, connecting the glucosyl donor by the succinyl bridge to position 6 of the glucosamine acceptor results in an alpha/beta-mixture of the corresponding disaccharides upon intramolecular glycosylation. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00729-6

文献信息

• Intramolecular glycosylation of prearranged glycosides part 5. α-(1→4)-Selective glucosylation of glucosides and glucosamines
  作者：Thomas Ziegler、Axel Ritter、Jürgen Hürttlen

  DOI：10.1016/s0040-4039(97)00729-6

  日期：1997.5

  The intramolecular (1 -->4) glucosylation of partially protected alkyl glucosides and glucosamines with phenyl 1-thioglucoside that is preconnected via its position 2 by a succinyl spacer to positions 3 of the glucosyl acceptor affords the alpha-linked disaccharides. The anomeric selectivity depends on the stereochemistry of the donor-acceptor-interaction and is not governed by neighboring group participation. In contrast, connecting the glucosyl donor by the succinyl bridge to position 6 of the glucosamine acceptor results in an alpha/beta-mixture of the corresponding disaccharides upon intramolecular glycosylation. (C) 1997 Elsevier Science Ltd.