methyl O⁴,O⁶-(R)-benzylidene-O³-methyl-α-D-arabino-2-deoxy-hexopyranoside | 53131-18-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl O⁴,O⁶-(R)-benzylidene-O³-methyl-α-D-arabino-2-deoxy-hexopyranoside
• 英文别名: (4aR,6S,8R,8aS)-6,8-dimethoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 53131-18-3
• 化学式: C₁₅H₂₀O₅
• 分子量: 280.321
• InChiKey: DHICYDCVZJTOAV-BUWKTABGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl O⁴,O⁶-(R)-benzylidene-O³-methyl-α-D-arabino-2-deoxy-hexopyranoside 在 吡啶 、 咪唑 、 camphor-10-sulfonic acid 、 碘 、 mercury(II) trifluoroacetate 、 sodium hydride 、 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 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 (5R,6S)-6-Benzyloxy-5-methoxy-cyclohex-2-enone
  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 3,4,6-tri-O-acetyl-2-deoxy-α-D-arabino-hexopyranoside 在 camphor-10-sulfonic acid 、 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl O⁴,O⁶-(R)-benzylidene-O³-methyl-α-D-arabino-2-deoxy-hexopyranoside
  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

文献信息

• An Efficient Deoxysugar Synthesis using Bu₄NBH₄via an S_N2 Reduction
  作者：Ken-ichi Sato、Toshio Hoshi、Yasuhiro Kajihara

  DOI：10.1246/cl.1992.1469

  日期：1992.8

  Deoxysugar derivatives were prepared from the corresponding triflate, tosylate, halogen, and epoxide derivatives. Employing the tetrabutylammonium tetrahydroborate reagent, the deoxygenation proceeds via an SN2 type displacement in good yield.

  脱氧糖衍生物由相应的三酸酯、对甲苯磺酸盐、卤素和环氧化物衍生物制备而成。利用四丁基四氢硼酸铵试剂，脱氧反应通过 SN2 型置换进行，收率很高。
• The synthesis of 3-deoxy-4-O-methyl-D-arabino-2-heptulosonic acid and its behaviour in the warren reaction
  作者：Daniel Charon、Ladislas Szabó

  DOI：10.1016/s0008-6215(00)82902-x

  日期：1974.6
• GIULIANO, ROBERT M.;BUZBY, JOHN H.;MARCOPULOS, NICHOLAS;SPRINGER, JAMES P+, J. ORG. CHEM., 55,(1990) N1, C. 3555-3562
  作者：GIULIANO, ROBERT M.、BUZBY, JOHN H.、MARCOPULOS, NICHOLAS、SPRINGER, JAMES P+

  DOI：——

  日期：——