GS 416 | 189758-78-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: GS 416
• 英文别名: (5R,6S)-5,6-bis(benzyloxy)cyclohex-2-enone；(5R,6S)-5,6-bis(phenylmethoxy)cyclohex-2-en-1-one
• CAS: 189758-78-9
• 化学式: C₂₀H₂₀O₃
• 分子量: 308.377
• InChiKey: PHZAKVRYDXRMRQ-WOJBJXKFSA-N

物化性质

• 沸点：
  455.5±45.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  GS 416 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 (2S,3R)-2,3-Bis-benzyloxy-cyclohexanone
  参考文献：
  名称：

  Novel γ-secretase inhibitors discovered by library screening of in-house synthetic natural product intermediates

  摘要：

  Screening of our in-house compound library comprised of intermediates of natural product synthesis projects resulted in discovering two novel gamma-secretase inhibitors, which coincidently had similar moieties, that is, cyclohexenone and two aryl groups arranged on the core six-membered ring. Structure-activity relationship studies of these compounds were also developed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.025
• 作为产物：
  描述：

  methyl 2-deoxy-D-glucopyranoside 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 碘 、 mercury(II) trifluoroacetate 、 sodium hydride 、 对甲苯磺酸 、 甲基磺酰氯 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 1.66h， 生成 GS 416
  参考文献：
  名称：

  Synthetic studies on antascomicin A: construction of the C18–C34 fragment

  摘要：

  Stereoselective synthesis of the C18-C34 fragment of antascomicin A is described. Construction of the C27-C34 carbocycle moiety was achieved via catalytic Ferrier carbocylization and Johnson-Claisen rearrangement, which was converted to iodide 2 by use of asymmetric alkylation and Sharpless epoxidation as key transformations. Coupling of iodide 2 and sulfone 3 furnished the C18-C34 fragment. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.04.072

文献信息

• Synthesis of the 2-Deoxyisomaltose Analogue of Acarbose by an Improved Route to Chiral Valieneamines
  作者：Tina M. Tagmose、Mikael Bols

  DOI：10.1002/chem.19970030318

  日期：——

  A 2-deoxyisomaltose analogue of acarbose was stereoselectively synthesised in 11 steps with a total yield of 7% starting from 2,6-dibromo-2, 6-dideoxy-D-mannono-1,4-lactone (6). The latter was reduced to the lactol, converted to the methyl glycoside (7) and hydrogenated to the methyl 6-bromo-2,6-dideoxyglycoside (8). Benzylation of the hydroxy groups, elimination of bromine to a 5-ene and Ferrier carbocyclisation

  从 2,6-dibromo-2, 6-dideoxy-D-mannono-1,4-lactone (6) 开始，通过 11 个步骤立体选择性合成了阿卡波糖的 2-脱氧异麦芽糖类似物，总收率为 7%。后者被还原为乳醇，转化为甲基糖苷 (7) 并氢化为甲基 6-溴-2,6-二脱氧糖苷 (8)。羟基的苄基化，溴消除成 5-烯和 Ferrier 碳环化得到 (2S, 3R)-2,3-bisbenzyloxycyclohex-5-enone (12)。在 –110°C 下 1, 2-加成苄氧基甲基锂得到叔醇 13 的 6:1 混合物；(1S) 异构体是主要的异构体。与异氰酸三氯乙酰酯反应得到氨基甲酸酯 19，当它脱水成氰酸酯时，自发地进行 [1,3] σ 重排成异氰酸酯，在加入甲醇后得到氨基甲酸甲酯 20。
• Novel γ-secretase inhibitors discovered by library screening of in-house synthetic natural product intermediates
  作者：Yasuko Takahashi、Haruhiko Fuwa、Akane Kaneko、Makoto Sasaki、Satoshi Yokoshima、Hifumi Koizumi、Tohru Takebe、Toshiyuki Kan、Takeshi Iwatsubo、Taisuke Tomita、Hideaki Natsugari、Tohru Fukuyama

  DOI：10.1016/j.bmcl.2006.04.025

  日期：2006.7

  Screening of our in-house compound library comprised of intermediates of natural product synthesis projects resulted in discovering two novel gamma-secretase inhibitors, which coincidently had similar moieties, that is, cyclohexenone and two aryl groups arranged on the core six-membered ring. Structure-activity relationship studies of these compounds were also developed. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthetic studies on antascomicin A: construction of the C18–C34 fragment
  作者：Haruhiko Fuwa、Yumiko Okamura、Hideaki Natsugari

  DOI：10.1016/j.tet.2004.04.072

  日期：2004.6

  Stereoselective synthesis of the C18-C34 fragment of antascomicin A is described. Construction of the C27-C34 carbocycle moiety was achieved via catalytic Ferrier carbocylization and Johnson-Claisen rearrangement, which was converted to iodide 2 by use of asymmetric alkylation and Sharpless epoxidation as key transformations. Coupling of iodide 2 and sulfone 3 furnished the C18-C34 fragment. (C) 2004 Elsevier Ltd. All rights reserved.