(3R)-1,3-O-benzylidine-1,3,4-butanetriol | 566934-88-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (3R)-1,3-O-benzylidine-1,3,4-butanetriol
• 英文别名: 2,4-O-benzylidene-(R)-1,2,4-butanetriol；1,3-Dioxane-4-methanol, 2-phenyl-, (4R)-；[(4R)-2-phenyl-1,3-dioxan-4-yl]methanol
• CAS: 566934-88-1
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: OLFYATZNXPXIAY-NFJWQWPMSA-N

物化性质

• 沸点：
  330.3±27.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  (3R)-1,3-O-benzylidine-1,3,4-butanetriol 在 pyridine-SO3 complex 作用下， 生成 Trimethyl-[(Z)-2-((R)-2-phenyl-[1,3]dioxan-4-yl)-1-phenylsulfanyl-vinyl]-silane
  参考文献：
  名称：

  Synthetic studies toward marine toxic polyethers (4) synthesis of segment -A of okadaic acid via -selectivity by heteroconjugate addition

  摘要：

  DOI：

  10.1016/s0040-4039(00)98903-2
• 作为产物：
  描述：

  苯甲醛二甲缩醛 、 (R)-(+)-1,2,4-丁三醇 在 氢气 作用下， 生成 (3R)-1,3-O-benzylidine-1,3,4-butanetriol
  参考文献：
  名称：

  Synthetic studies toward marine toxic polyethers (4) synthesis of segment -A of okadaic acid via -selectivity by heteroconjugate addition

  摘要：

  DOI：

  10.1016/s0040-4039(00)98903-2

文献信息

• Neoglycoconjugates from synthetic tetra- and hexasaccharides that mimic the terminus of the O-PS of Vibrio cholerae O:1, serotype Inaba
  作者：Xingquan Ma、Rina Saksena、Anatoly Chernyak、Pavol Kováč

  DOI：10.1039/b211660j

  日期：2003.2.27

  nic acid side chain already attached have been prepared and used for the synthesis of the di-through to the hexasaccharide that mimic the upsteam terminus of the O-specific polysaccharide of Vibrio cholerae O:1, serotype Inaba. The target tetra- and the hexasaccharide, which were obtained in the form of 5-methoxycarbonylpentyl glycosides, were linked to BSA using squaric acid diester chemistry. The

  已经制备了具有已连接的N-3-脱氧-L-甘油-四氢电子酸侧链的糖基受体和糖基供体，并将其用于合成模仿O-的上游端的六糖的二通。霍乱弧菌O：1血清型Inaba的特定多糖。使用方酸二酯化学方法将以5-甲氧基羰基戊基糖苷形式获得的目标四糖和六糖与BSA连接。通过表面增强的激光解吸电离飞行时间质谱仪（SELDI-TOF MS）监测共轭反应。当达到所需的半抗原/ BSA摩尔比时，这可以控制合成寡糖的结合过程，并终止反应，产生具有预定碳水化合物/载体比的新糖缀合物。通过SELDI-TOF MS技术监测结合的能力，使得在一锅反应中从一个半抗原中制备出几种具有不同预定碳水化合物/载体比的新糖结合物成为可能。
• Synthesis and Antitumor Activity of Ether Glycerophospholipids Bearing a Carbamate Moiety at the sn-2 Position: Selective Sensitivity Against Prostate Cancer Cell Lines
  作者：Hoe-Sup Byun、Robert Bittman、Pranati Samadder、Gilbert Arthur

  DOI：10.1002/cmdc.201000060

  日期：——

  Analogues of 1‐O‐hexadecyl‐sn‐3‐glycerophosphonocholine (compounds 1–4) or sn‐3‐glycerophosphocholine (compound 5) bearing a carbamate or dicarbamate moiety at the sn‐2 position were synthesized and evaluated for their antiproliferative activity against cancer cells derived from a variety of tissues. Although all of the compounds are antiproliferative, surprisingly the carbamates (1 and 2) are more

  1-类似物ö -hexadecyl- SN -3- glycerophosphonocholine（化合物1 - 4）或SN -3-甘油（化合物5）的轴承在氨基甲酸酯或氨基甲酸酯部分SN -2位置被合成并评价了它们对抗增殖活性癌细胞来源于各种组织。尽管所有化合物均具有抗增殖作用，但令人惊讶的是，氨基甲酸酯（1和2）对激素非依赖性细胞株DU145和PC3的抵抗力要强于我们研究的其他癌细胞系。二氨基甲酸酯（3和4）。胆碱磷酸氨基甲酸酯类似物5是作为对前列腺癌细胞系作为相应phosphonocholine类似物有效1。由胱天蛋白酶激活和线粒体膜电位丧失评估，由2'-（三甲基铵）乙基4-十六烷基氧基-3（ R） -N-甲基氨基甲酰基-1-丁烷膦酸酯（氨基甲酸酯类似物2）诱导的细胞死亡似乎是由凋亡介导的。 。在鼠前列腺癌异种移植模型中评估2的体内活性。口服和静脉给药显示2对抑制Rag2M小鼠中PC3
• Synthesis of Glycerolipid Carbamates and Dicarbamates and Their Use as an Antitumor Compounds
  申请人：Bittman Robert

  公开号：US20090042811A1

  公开（公告）日：2009-02-12

  The syntheses and in vitro antitumor properties of carbamate-containing, dicarbamate-containing, and ureido-containing phospholipid compounds that have an ether linkage at the C-1 position of a glycerol backbone, a carbamate, dicarbamate, or ureido moiety at the C-2 position of the glycerol backbone, and a phosphocholine, phosphonocholine, or glycoside moiety at the C-3 position of the glycerol backbone are described. The synthesis and antiproliferative activity of ether lipids with a naphthol moiety at the C-1 position are also described. These compounds were shown to be potent inhibitors of cancer cell growth. These compounds are useful for killing cancer cells and treating cancer.

  本文描述了在甘油骨架的C-1位置具有醚键的氨基甲酸酯，双氨基甲酸酯和尿素含有物，C-2位置具有氨基甲酸酯，双氨基甲酸酯或尿素基团，并在C-3位置具有磷酸胆碱，磷酸胆碱或糖苷基团的磷脂化合物的合成和体外抗肿瘤性质。 本文还描述了在C-1位置具有萘酚基团的醚脂类化合物的合成和抗增殖活性。这些化合物被证明具有强大的抑制癌细胞生长的能力。这些化合物可用于杀死癌细胞和治疗癌症。
• NUCLEOSIDE ANALOGUES AND METHODS OF USE THEREOF
  申请人：LCB PHARMA INC.

  公开号：US20190322693A1

  公开（公告）日：2019-10-24

  Nucleoside analogues that can be used as anticancer or antiviral agents are presented. These compounds are nucleoside and/or nucleotide prodrugs. In particular, the subject matter relates to nucleoside analogues comprising a tetrahydrofuranyl, or tetrahydrothienyl moiety which: have a quaternary stereogenic all-carbon center at the 3′ position and bear a phosphoryl group at either one of, or both of positions C5′ and/or C3′; have a quaternary stereogenic all-carbon center at one of the 3′ position, 2′ position, or no quaternary stereogenic center at all, and bear a β-blocked lipoate derivative attached through an amide bond to the primary amine of the nucleobase; or have a quaternary stereogenic all-carbon center at the 2′ position and bear a phosphorylated prodrug at the C5′-position and a β-blocked lipoate derivative attached through an amide bond to the primary amine of the nucleobase.
• US8153615B2
  申请人：——

  公开号：US8153615B2

  公开（公告）日：2012-04-10