(2S,3S,6S)-6-Methoxy-2-methyl-3,6-dihydro-2H-pyran-3-ol | 63902-58-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2S,3S,6S)-6-Methoxy-2-methyl-3,6-dihydro-2H-pyran-3-ol
• CAS: 63902-58-9
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: BPAHQTJCFQUBHC-ACZMJKKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S,6S)-6-Methoxy-2-methyl-3,6-dihydro-2H-pyran-3-ol 在 三乙基硅烷 、 四(三苯基膦)钯 、 正丁基锂 、 四氯化钛 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 diethyl 2-[(3S,6S)-6-methyl-3,6-dihydro-2H-pyran-3-yl]propanedioate
  参考文献：
  名称：

  Regioselectivity in the Palladium-Catalyzed Addition of Carbon Nucleophiles to Dihydropyran Derivatives

  摘要：

  The regioselectivity of Pd-catalyzed malonate or sulfonylacetate addition to dihydropyran derivatives is highly dependent upon the substitution pattern of the dihydropyran nucleus and is governed by electronic, rather than steric factors. In certain instances, subtle steric features also play a role in controlling regioselectivity by altering the conformation of the intermediate eta(3)-allyl Pd-complex.

  DOI：

  10.1021/jo961973d
• 作为产物：
  描述：

  6-hydroxy-2-methyl-2H-pyran-3(6H)-one 在 sodium tetrahydroborate 、 cerium(III) chloride 、 silver(l) oxide 作用下， 生成 (2S,3S,6S)-6-Methoxy-2-methyl-3,6-dihydro-2H-pyran-3-ol
  参考文献：
  名称：

  Regioselectivity in the Palladium-Catalyzed Addition of Carbon Nucleophiles to Dihydropyran Derivatives

  摘要：

  The regioselectivity of Pd-catalyzed malonate or sulfonylacetate addition to dihydropyran derivatives is highly dependent upon the substitution pattern of the dihydropyran nucleus and is governed by electronic, rather than steric factors. In certain instances, subtle steric features also play a role in controlling regioselectivity by altering the conformation of the intermediate eta(3)-allyl Pd-complex.

  DOI：

  10.1021/jo961973d

文献信息

• Catalyst-Controlled Stereoselective <i>O</i>-Glycosylation: Pd(0) vs Pd(II)
  作者：Hui Yao、Shasha Zhang、Wei-Lin Leng、Min-Li Leow、Shaohua Xiang、Jingxi He、Hongze Liao、Kim Le Mai Hoang、Xue-Wei Liu

  DOI：10.1021/acscatal.7b01630

  日期：2017.8.4

  Stereoselective construction of various O-glycosidic bonds was first achieved by different palladium sources using 3,4-O-carbonate galactal as the donor to reach yields up to 95% under mild conditions. With Pd(II) catalyst coordination of this glycal donor from the β-face directed by carbonate group, hard nucleophiles (aliphatic alcohols) gave β-glycosides and α-glycosides were obtained from soft nucleophiles

  各种O-糖苷键的立体选择性构建首先是通过使用3,4- O-碳酸半乳糖作为供体，通过不同的钯源实现的，在温和的条件下，收率可达95％。用Pd（II）催化剂从由碳酸酯基团定向的β面配位该糖基供体，硬的亲核试剂（脂族醇）得到β-糖苷，而α-糖苷则从软的亲核试剂（苯酚）制得。相比之下，由于空间效应，Pd（0）催化剂从β面上配位给体，硬受体和软受体都只能通过氢键介导的糖苷配基生成β-糖苷。
• Szechner; Achmatowicz; Badowska-Roslonek, Polish Journal of Chemistry, 1999, vol. 73, # 7, p. 1133 - 1141
  作者：Szechner、Achmatowicz、Badowska-Roslonek

  DOI：——

  日期：——