(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)phenylmethane | 155590-31-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)phenylmethane
• 英文别名: (2S,3S,4R,5R,6R)-2-benzyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 155590-31-1
• 化学式: C₄₁H₄₂O₅
• 分子量: 614.781
• InChiKey: JBWSLLXQJLSPLM-XWASVSOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  46
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)phenylmethane 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以99%的产率得到1-C-β-D-glucopyranosyl-1-phenylmethane
  参考文献：
  名称：

  Suzuki Cross-Coupling of Carbohydrates: Synthesis of β-Arylmethyl-C-glycosides and Aryl-Scaffolded Trisaccharide Mimics

  摘要：

  已合成D-葡萄糖和D-甘露糖的β-1-C-芳基甲基糖苷衍生物，采用温和的氢硼化/铃木交叉偶联序列。描述了该方法的适用范围和局限性，以及其在构建芳基支架三糖类似物方面的扩展。

  DOI：

  10.1055/s-0030-1260180
• 作为产物：
  描述：

  (3R,4R,5S)-4,5-Bis-benzyloxy-3-benzyloxymethyl-2,7-dioxa-bicyclo[4.1.0]heptane 在 sodium hydride 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)phenylmethane
  参考文献：
  名称：

  Cytotoxic effects of C-glycosides in HOS and HeLa cell lines

  摘要：

  Fifty-two C-glycosides were synthesized and their in-vitro antiproliferative activity screened against human cervical carcinoma (HeLa) and osteosarcoma (HOS) cell lines. Nine of them had growth inhibitions (GI(50) values) below 10 mu M, the Gglucopyranoside 38 being the most active against HeLa (5.4 mu M) and the dichlorocyclopropyl derivative 42 against HOS (1.6 mu M). Some preliminary structure-activity relationships were established. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.060

文献信息

• Bicyclic carbohydrate compounds useful in the treatment of infections caused by herpesviridae
  申请人：Sas Benedikt

  公开号：US20050090452A1

  公开（公告）日：2005-04-28

  Bicyclic carbohydrates for the treatment of infections caused by herpseviridae, and in particular cytomegalovirus. The invention consists of the novel bicyclic carbohydrates the generic structure of which is: wherein R 1 is either -Bn or -Ph; R 2 and R 3 are either -alkyl, -aryl, -allyl, or —H; R 4 and R 5 form a ring and are either —CH(Ph)- or —CH(aryl)- and X is either O, N or S.

  用于治疗由疱疹病毒科感染引起的感染，特别是巨细胞病毒的双环碳水化合物。该发明包括新型双环碳水化合物，其通用结构如下：其中R1为-Bn或-Ph；R2和R3为-烷基，-芳基，-烯丙基或-H；R4和R5形成一个环，可以是-CH(Ph)-或-CH(芳基)-，X可以是O，N或S。
• Bicyclic carbohydrates as antiviral bioactives for the treatment of infections caused by the alphaherpesvirinae HSV-1 and HSV-2
  申请人：Sas Benedikt

  公开号：US20050059612A1

  公开（公告）日：2005-03-17

  Novel bicyclic carbohydrate compounds are effective for the prophylaxis and treatment of diseases caused by infections of the alphaherpesvirinae HSV-1 and HSV-2. The invention includes the compound wherein X 1 , X 2 , and X 3 are selected from the group consisting of O, N, and S; wherein Y 1 and Y 2 are selected from the group consisting of O, N, and S; and wherein Z is selected from the group consisting of F, Cl, and Br, as well as analogs, prodrugs and pharmaceutically acceptable salts thereof, together with pharmaceutical compositions for the prophylaxis and treatment of diseases caused by infections of alphaherpesvirinae.

  新型的双环碳水化合物对由α-疱疹病毒亚科HSV-1和HSV-2感染引起的疾病的预防和治疗具有有效性。该发明包括化合物，其中X1、X2和X3选自O、N和S组成的群体；Y1和Y2选自O、N和S组成的群体；Z选自F、Cl和Br组成的群体，以及其类似物、前药和药学上可接受的盐，以及用于预防和治疗由α-疱疹病毒亚科感染引起的疾病的药物组合物。
• Suzuki Cross-Coupling of Carbohydrates: Synthesis of β-Arylmethyl-C-glycosides and Aryl-Scaffolded Trisaccharide Mimics
  作者：Carl R. Johnson、Brian A. Johns

  DOI：10.1055/s-0030-1260180

  日期：——

  β-1-C-Arylmethylglycoside derivatives of D-glucose and D-mannose have been synthesized using a mild hydroboration/Suzuki cross-coupling sequence. The scope and limitations of this methodology as well as its extension to the construction of aryl scaffolded trisaccharide mimics is described.

  已合成D-葡萄糖和D-甘露糖的β-1-C-芳基甲基糖苷衍生物，采用温和的氢硼化/铃木交叉偶联序列。描述了该方法的适用范围和局限性，以及其在构建芳基支架三糖类似物方面的扩展。
• A new oxa-Michael reaction and a gold-catalysed cyclisation en route to C-glycosides
  作者：Sébastien Redon、Michel Wierzbicki、Joëlle Prunet

  DOI：10.1016/j.tetlet.2013.02.022

  日期：2013.4

  Two new syntheses of benzyl C-glycosides have been developed. The first one involves an unprecedented oxa-Michael cyclisation and the second one relies on an efficient gold-catalysed ring-closure. (c) 2013 Elsevier Ltd. All rights reserved.
• Panigot, M. J.; Humphries, K. A.; Curley, R. W., Journal of Carbohydrate Chemistry, 1994, vol. 13, # 2, p. 303 - 322
  作者：Panigot, M. J.、Humphries, K. A.、Curley, R. W.

  DOI：——

  日期：——