1,2-O-isopropylidene-3-O-methoxyethoxymethyl-rac-glycerol | 115406-37-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-isopropylidene-3-O-methoxyethoxymethyl-rac-glycerol
• 英文别名: (4RS)-2,2-dimethyl-4-(2-methoxyethoxy)methoxymethyl-1,3-dioxolane；4-(2-methoxyethoxymethoxymethyl)-2,2-dimethyl-1,3-dioxolane
• CAS: 115406-37-6
• 化学式: C₁₀H₂₀O₅
• 分子量: 220.266
• InChiKey: SNZTZALANCVODF-UHFFFAOYSA-N

物化性质

• 沸点：
  265.6±30.0 °C(predicted)
• 密度：
  1.022±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  1,2-O-isopropylidene-3-O-methoxyethoxymethyl-rac-glycerol 在 对甲苯磺酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以91%的产率得到1-O-methoxyethoxymethyl-rac-glycerol
  参考文献：
  名称：

  新型的含二硫的大环二酰基甘油的合成

  摘要：

  合成了新的在酰基侧链之间包含分子内二硫键的二酰基甘油（2-4）。由于二硫键单元位置的不同，本方法允许合成大小变化的大环。

  DOI：

  10.1016/0040-4039(96)01181-1
• 作为产物：
  描述：

  2-甲氧基乙氧基甲基氯 、 丙酮缩甘油 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以80%的产率得到1,2-O-isopropylidene-3-O-methoxyethoxymethyl-rac-glycerol
  参考文献：
  名称：

  新型的含二硫的大环二酰基甘油的合成

  摘要：

  合成了新的在酰基侧链之间包含分子内二硫键的二酰基甘油（2-4）。由于二硫键单元位置的不同，本方法允许合成大小变化的大环。

  DOI：

  10.1016/0040-4039(96)01181-1

文献信息

• Isothiazolyl substituted glycerol derivatives containing phosphate groups
  申请人：Sankyo Company, Limited

  公开号：US05068340A1

  公开（公告）日：1991-11-26

  Glycerol derivatives having at least one heterocyclic group on the 1 or 2 position are PAF antagonists which may be used to treat asthma, inflammation and shock.

  在1或2位置上至少具有一个杂环基团的甘油衍生物是PAF拮抗剂，可用于治疗哮喘、炎症和休克。
• Glycerol derivatives, their preparation and their therapeutic use
  申请人：Sankyo Company Limited

  公开号：EP0238202A2

  公开（公告）日：1987-09-23

  Glycerol derivatives having at least one heterocyclic group on the 3 or 2 position and a group of formula -Y-D-Q on the 1 position (in which Y represents oxygen, sulphur, -NR3-, -X-CO-R'-, -R4-CO-X-, -NR'-CO-, -CO-NR3-or -X-P-(O) (OH)-O-, where -NR3-is optionally protected imino, R4 represents a direct bond or -NR3; and X represents oxygen or sulphur; D represents optionally substituted C1-C14 alkylene; and Q represents a nitrogen-containing heterocyclic group or an amino group either of which is optionally quatemized) are PAF antagonists which may be used to treat asthma, inflammation and shock. They may be prepared by reacting a glycerol derivative having an active group at the 1-position with an appropriate compound to introduce the desired group.

  甘油衍生物在 3 或 2 位上至少有一个杂环基团，在 1 位上有一个式-Y-D-Q 的基团（其中 Y 代表氧、硫、-NR3-、-X-CO-R'-、-R4-CO-X-、-NR'-CO-、-CO-NR3-或 -X-P-(O)(OH)-O-，其中 -NR3- 是可选的受保护亚氨基，R4 代表直接键或 -NR3；X 代表氧或硫；D 代表任选取代的 C1-C14 亚烷基；Q 代表含氮杂环基团或氨基，二者任选其一被藜麦化）是 PAF 拮抗剂，可用于治疗哮喘、炎症和休克。制备方法是将 1 位具有活性基团的甘油衍生物与适当的化合物反应，引入所需的基团。
• Synthesis of Macrocyclic Diacyl/Dialkyl Glycerols Containing Disulfide Tether and Studies of Their Effects upon Incorporation in DPPC Membranes. Implications in the Design of Phospholipase A₂ Modulators
  作者：Santanu Bhattacharya、Sangita Ghosh、Kalpathy R. K. Easwaran

  DOI：10.1021/jo980866b

  日期：1998.12.1

  A general method for the preparation of novel disulfide-tethered macrocyclic diacylglycerols (DAGs) has been described. Overall synthesis involved stepwise protection, acylation, and deprotection to yield the bis(omega-bromoacyl) glycerols. In the crucial macrocyclization step, a unique reagent, benzyltriethylammonium tetrathiomolybdate (BTAT), has been used to convert individual bis(omega-bromoacyl) glycerols to their respective macrocyclic disulfides. DAG 6, which had ether linkages between hydrocarbon chains and the glycerol backbone, was also synthesized from an appropriate precursor using a similar protocol. One of the DAGs (DAG 5) had a carbon-carbon tether instead of a disulfide one and was synthesized using modified Glaser coupling. Preparation of alpha-disulfide-tethered DAG (DAG 4) required an alternative method, as treatment of the bisbromo precursor with BTAT gave a mixture of several compounds from which separation of the target molecule was cumbersome. To avoid this problem, the bisbromide was converted to its corresponding dithiocyanate, which on further treatment with BTAT yielded the desired DAG (DAG 4) in good yield. Upon treatment with the reducing agent dithiothreitol (DTT), the DAGs that contain a disulfide tether could be quantitatively converted to their "open-chain" thiol analogues. These macrocyclic DAGs and their reduced "open-chain" analogues have been incorporated in DPPC vesicles to study their effect on model membranes. Upon incorporation of DAG 1 in DPPC vesicles, formation of new isotropic phases was observed by P-31 NMR, These isotropic phases disappeared completely on opening the macrocyclic ring by a reducing agent. The thermotropic properties of DPPC bilayers having DAGs (1-6) incorporated at various concentrations were studied by differential scanning calorimetry. Incorporation of DAGs in general reduced the cooperativity unit (CU) of the vesicles. Similar experiments with reduced "open-chain" DAGs incorporated in a DPPC bilayer indicated a recovery of CU with respect to their macrocyclic "disulfide" counterparts. The effect of inclusion of these DAGs on the activity of phospholipase A(2) (PLA(2)) was studied in vitro. Incorporation of DAC 1 in DPPC membranes potentiated both bee venom and cobra venom PLA(2) activities.
• Synthesis of 1-O-(8-[18F]fluorooctanoyl)-2-O-palmitoyl-rac-glycerol for imaging intracellular signal transduction
  作者：Shozo Furumoto、Ren Iwata、Tatsuo Ido

  DOI：10.1002/1099-1344(20001030)43:12<1159::aid-jlcr402>3.0.co;2-z

  日期：2000.10.30

  An improved approach to the synthesis of 1-O-(8-[F-18]fluorooctanoyl)-2-O-palmitoyl-rac-glycerol (rac-1,2-[F-18]FDAG) has been developed. We designed and synthesized two new types of precursors for the radiosynthesis and investigated their general utility. Each precursor was smoothly radiofluorinated (5 min) and the protecting soup at the 3-O-position was rapidly removed (1 min). The resulting rac-1,2-[F-18]FDAG was obtained in overall radiochemical yields of 20-30% (EOB) within 70 min including final preparative HPLC separation.
• Furumoto; Nagata; Iwata, Journal of labelled compounds and radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S644-S645
  作者：Furumoto、Nagata、Iwata、Ido

  DOI：——

  日期：——