(4S,5R)-4-hydroxymethyl-2,2-dimethyl-[1,3]dioxan-5-ol | 302578-99-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5R)-4-hydroxymethyl-2,2-dimethyl-[1,3]dioxan-5-ol
• 英文别名: 2,4-O-isopropylidene-D-erythritol；(2S,3R)-Butan-1,2,3,4-tetraol 2,4-isopropylidene acetal；(4S,5R)-4-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-5-ol
• CAS: 302578-99-0
• 化学式: C₇H₁₄O₄
• 分子量: 162.186
• InChiKey: ODWXYNAGEJVSQH-RITPCOANSA-N

物化性质

• 沸点：
  284.3±25.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5R)-4-hydroxymethyl-2,2-dimethyl-[1,3]dioxan-5-ol 在 ruthenium trichloride sodium periodate 、 氯化亚砜 、 三乙胺 作用下， 以 四氯化碳 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 13.67h， 生成
  参考文献：
  名称：

  Synthesis of salacinol

  摘要：

  Salacinol, a new type of alpha-glucosidase inhibitor discovered from the antidiabetic herb, was synthesized for the first time. Under the strategy that salacinol would be synthesized by the coupling reaction between 1,4-epithio-D-arabinitol and the cyclic sulfate of an erythritol derivative, the model coupling reactions between tetrahydrothiophene and versatile cyclic sulfate derivatives were undertaken. These experiments indicated that the 1,3-diol of the cyclic sulfate should be protected with the isopropylidene group, otherwise, even the benzylidene-protected cyclic sulfate decomposed during the reaction. Thus, the salacinol was synthesized using the cyclic sulfate of 1,3-O-isopypropylidene-D-erythritol. The resulting coupling product was deisopropylidenated to afford salacinol. A diastereomer of salacinol was also synthesized. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01129-1
• 作为产物：
  描述：

  4,6-O-isopropylidene-D-glucopyranose 在 sodium tetrahydroborate 、 sodium periodate 、 溴甲酚绿 、 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 反应 5.17h， 生成 (4S,5R)-4-hydroxymethyl-2,2-dimethyl-[1,3]dioxan-5-ol
  参考文献：
  名称：

  Synthesis of salacinol

  摘要：

  Salacinol, a new type of alpha-glucosidase inhibitor discovered from the antidiabetic herb, was synthesized for the first time. Under the strategy that salacinol would be synthesized by the coupling reaction between 1,4-epithio-D-arabinitol and the cyclic sulfate of an erythritol derivative, the model coupling reactions between tetrahydrothiophene and versatile cyclic sulfate derivatives were undertaken. These experiments indicated that the 1,3-diol of the cyclic sulfate should be protected with the isopropylidene group, otherwise, even the benzylidene-protected cyclic sulfate decomposed during the reaction. Thus, the salacinol was synthesized using the cyclic sulfate of 1,3-O-isopypropylidene-D-erythritol. The resulting coupling product was deisopropylidenated to afford salacinol. A diastereomer of salacinol was also synthesized. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01129-1

文献信息

• Intramolecular Radical CyclizationRing-Closing Metathesis Approach to Fused Polycyclic Ethers. Convergent Synthesis and Conformational Analysis of the (E)FGH Ring System of Ciguatoxin
  作者：Makoto Sasaki、Tetsuji Noguchi、Kazuo Tachibana

  DOI：10.1021/jo010974p

  日期：2002.5.1

  A convergent synthetic route to the (E)FGH ring system 4 of ciguatoxins, the causative toxins for ciguatera fish poisoning, has been developed. The synthesis features convergent coupling to form dioxane acetal, regioselective acetal cleavage by diethylaluminum phenylthiolate or diisobutylaluminum phenylselenolate followed by intramolecular radical cyclization to construct the oxepane ring G, and a

  已经开发出一种合成的合成路线，可通往雪茄鱼中毒的致病毒素-雪茄毒素的（E）FGH环系统4。该合成具有会聚偶联形成二恶烷缩醛，苯硫醇二乙基铝或苯硒酸二异丁酯铝的区域选择性缩醛裂解，随后分子内自由基环化以构建氧杂环丁烷环G和闭环易位反应以形成六氢氧肟酮环F的特征。四环模型系统4以两种构象（UP和DOWN构象）的5：1平衡混合物形式存在，其中UP占主导地位。这是第一个说明了对UP构象子比对DOWN构象子的偏好的例证，对天然雪茄毒素的偏好被发现。