4-[(2S,3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-phenylsulfanyloxan-3-yl]oxy-4-oxobutanoic acid | 191216-55-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[(2S,3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-phenylsulfanyloxan-3-yl]oxy-4-oxobutanoic acid
• CAS: 191216-55-4
• 化学式: C₃₇H₃₈O₈S
• 分子量: 642.77
• InChiKey: ZUXLXDPVGBGINA-GPGBMJNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  46
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-[(2S,3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-phenylsulfanyloxan-3-yl]oxy-4-oxobutanoic acid 在 盐酸 、 4-二甲氨基吡啶 、 sodium cyanoborohydride 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 吡啶 、 乙醚 为溶剂， 反应 24.17h， 生成 4-O-[(2S,3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-phenylsulfanyloxan-3-yl] 1-O-[(2R,3R,4R,5S,6R)-3-(1,3-dioxoisoindol-2-yl)-5-hydroxy-2-phenylmethoxy-6-(phenylmethoxymethyl)oxan-4-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
• 作为产物：
  描述：

  丁二酸酐 、 Phenyl 3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 反应 48.0h， 以89%的产率得到4-[(2S,3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-phenylsulfanyloxan-3-yl]oxy-4-oxobutanoic acid
  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.