苄基 2-脱氧-2-(1,3-二氢-1,3-二氧代-2H-异吲哚-2-基)-4,6-O-(苯基亚甲基)-beta-D-吡喃葡萄糖苷 | 80035-33-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 中文名称: 苄基 2-脱氧-2-(1,3-二氢-1,3-二氧代-2H-异吲哚-2-基)-4,6-O-(苯基亚甲基)-beta-D-吡喃葡萄糖苷
• 中文别名: 苄基2-脱氧-2-邻苯二甲酰亚胺-4,6-O-亚苄基-β-D-吡喃葡萄糖苷；苄基 2-脱氧-2-(1,3-二氢-1,3-二氧代-2H-异吲哚-2-基)-4,6-O-(苯基亚甲基)-BETA-D-吡喃葡萄糖苷
• 英文名称: benzyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside
• 英文别名: benzyl-4,6-O-benzylidene-2-deoxy-2-phthalamido-β-D-glucopyranoside；2-((4AR,6R,7R,8R,8aS)-6-(benzyloxy)-8-hydroxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)isoindoline-1,3-dione；2-[(4aR,6R,7R,8R,8aS)-8-hydroxy-2-phenyl-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]isoindole-1,3-dione
• CAS: 80035-33-2
• 化学式: C₂₈H₂₅NO₇
• 分子量: 487.509
• InChiKey: XUBZHIFTRFYZLL-XSVWMRDFSA-N

物化性质

• 熔点：
  180-182°C
• 沸点：
  685.1±55.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3 (20 ºC 760 Torr)
• 溶解度：
  可溶于氯仿、可溶于二氯甲烷、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  94.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  苄基 2-脱氧-2-(1,3-二氢-1,3-二氧代-2H-异吲哚-2-基)-4,6-O-(苯基亚甲基)-beta-D-吡喃葡萄糖苷 在 palladium on activated charcoal 盐酸 、 4 A molecular sieve 、 sodium hydride 、 溶剂黄146 、 三丁基氧化锡 、 mercury dibromide 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 67.75h， 生成 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl(1<*>4)-2-deoxy-2-phthalimido-3,6-di-O-acetyl-β-D-glucopyranosyl chloride
  参考文献：
  名称：

  Synthesis of 3,6-di-O-acetyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)-β-d-glucopyranosyl chloride

  摘要：

  DOI：

  10.1016/s0008-6215(00)80526-1
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose 在 camphor-10-sulfonic acid 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 27.0h， 生成 苄基 2-脱氧-2-(1,3-二氢-1,3-二氧代-2H-异吲哚-2-基)-4,6-O-(苯基亚甲基)-beta-D-吡喃葡萄糖苷
  参考文献：
  名称：

  Synthesis ofN-acetyl Glucosamine Analogs as Inhibitors for Hyaluronan Biosynthesis

  摘要：

  Elevated hyaluronan expression is a hallmark of many types of cancer. Therefore, inhibition of hyaluronan biosynthesis can potentially slow the growth of tumor cells. Herein, we explore a chain termination strategy to reduce hyaluronan synthesis by tumor cells. Several analogs of glucosamine were prepared, which contained modifications at the C-3 positions. These analogs can possibly cap the nonreducing end of a growing hyaluronan chain, thus lowering the amount of hyaluronan synthesized. Upon incubation with pancreatic cancer cells, a fluorine-containing glucosamine analog was found to exhibit significant inhibitory activities of hyaluronan synthesis. Furthermore, it drastically reduced the proliferation of cancer cells. Supplemental materials are available for this article. Go to the publisher's online edition of Journal of Carbohydrate Chemistry to view the supplemental file.

  DOI：

  10.1080/07328303.2013.815196

文献信息

• Lipid A analog as stimulant for production of interleukin-1 in human
  申请人：E. I. Du Pont de Nemours and Company

  公开号：US05158941A1

  公开（公告）日：1992-10-27

  This invention concerns the use of synthetic Lipid A analog P9132 to activate human monocytes, and inhibit growth of tumor cells.

  这项发明涉及使用合成的脂多糖A类似物P9132来激活人类单核细胞，并抑制肿瘤细胞的生长。
• Wang, Lai-Xi; Li, Chuan; Wang, Qin-Wei, Journal of the Chemical Society. Perkin transactions I, 1994, # 6, p. 621 - 628
  作者：Wang, Lai-Xi、Li, Chuan、Wang, Qin-Wei、Hui, Yong-Zheng

  DOI：——

  日期：——
• 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.
• US5158941A
  申请人：——

  公开号：US5158941A

  公开（公告）日：1992-10-27
• US5352811A
  申请人：——

  公开号：US5352811A

  公开（公告）日：1994-10-04