2S-benzyloxymethyl-4S acetoxy-1,3 dioxolane | 154459-77-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2S-benzyloxymethyl-4S acetoxy-1,3 dioxolane
• 英文别名: [(2S,4S)-2-(phenylmethoxymethyl)-1,3-dioxolan-4-yl] acetate
• CAS: 154459-77-5
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: WXFZXUOIQZWGEX-QWHCGFSZSA-N

物化性质

• 沸点：
  362.0±42.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2S-benzyloxymethyl-4R-acetoxy-1,3 dioxolane 、 2S-benzyloxymethyl-4S acetoxy-1,3 dioxolane 在 碘代三甲硅烷 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 2S-Benzyloxymethyl-4R-iodo-1,3-dioxolane 、 2S-benzyloxymethyl-4S-iodo-1,3 dioxolane
  参考文献：
  名称：

  Method and compositions for the synthesis of dioxolane nucleosides with

  摘要：

  本发明涉及制备含有1,3-二氧兰糖环的生物重要核苷类似物的方法和组合物。特别地，本发明涉及通过在约-10℃的温度下用式（II）的中间体对碱基进行糖基化来立体选择性地合成β（顺式）异构体的方法。其中，R1和L在此定义。

  公开号：

  US05922867A1
• 作为产物：
  描述：

  苄氧基乙醛二甲基乙缩醛 在 吡啶 、 ruthenium trichloride 、 sodium hypochlorite 、 苄基三乙基氯化铵 、 双氧水 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 2S-benzyloxymethyl-4S acetoxy-1,3 dioxolane
  参考文献：
  名称：

  Divergent asymmetric syntheses of dioxolane nucleoside analogues

  摘要：

  Oxidative degradation of benzyloxymethylacetals derived from D-mannitol or L-ascorbic acid provides dioxolane intermediate 6 and 7 useful in the synthesis of all the stereoisomers of dioxolane nucleoside analogues.

  DOI：

  10.1016/s0957-4166(00)80092-0

文献信息

• Methods of treating cancer using a combination of drugs
  申请人：Shire BioChem Inc.

  公开号：US20030027799A1

  公开（公告）日：2003-02-06

  The present invention provides a novel method for treating a patient with cancer comprising administering to the patient a therapeutically effective amount of cisplatin and a compound having the formula I: 1 wherein B is cytosine or 5-fluorocytosine and R is selected from the group comprising H, monophosphate, diphosphate, triphosphate, carbonyl substituted with a C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, and 2 wherein each Rc is independently selected from the group comprising H, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl and a hydroxy protecting group.

  本发明提供了一种治疗癌症患者的新方法，包括向患者施用治疗有效量的顺铂和具有以下式子I的化合物：1其中B为胞嘧啶或5-氟胞嘧啶，R选自包括H、单磷酸、二磷酸、三磷酸、羰基取代的C1-6烷基、C2-6烯基、C2-6炔基、C6-10芳基和2其中每个Rc独立地选自包括H、C1-6烷基、C2-6烯基、C2-6炔基和羟基保护基的群。
• Methods of treating leukemia
  申请人：BioChem Pharma Inc.

  公开号：US20020107225A1

  公开（公告）日：2002-08-08

  The present invention provides a novel method for treating leukemia and more particularly acute myelogenous leukemia (AML) in a host comprising administering to the host a therapeutically effective amount of a compound having the formula I: 1 wherein B is cytosine or 5-fluorocytosine and R is selected from the group comprising H, monophosphate, diphosphate, triphosphate, carbonyl substituted with a C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 6-10 aryl, and 2 wherein each Rc is independenty selected from the group comprising H, C 1-6 alkyl, C 2-6 alkynyl and an hydroxy protecting group; and wherein said compound is substantially in the form of the (−) enantiomer.

  本发明提供了一种治疗白血病，特别是急性髓性白血病（AML）的新方法，包括向宿主施加具有I式的化合物的治疗有效量：1其中B是胞嘧啶或5-氟胞嘧啶，R选自H，单磷酸，二磷酸，三磷酸，羰基被C1-6烷基，C2-6烯基，C2-6炔基，C6-10芳基和2取代，其中每个Rc独立地选自H，C1-6烷基，C2-6炔基和羟基保护基; 以及其中所述的化合物基本上是（-）对映体。
• [EN] STEREOSELECTIVE SYNTHESIS OF NUCLEOSIDE ANALOGUES<br/>[FR] SYNTHESE STEREOSELECTIVE D'ANALOGUES NUCLEOSIDIQUES
  申请人：IAF BIOCHEM INT

  公开号：WO2000047759A1

  公开（公告）日：2000-08-17

  The present invention provides a process for making stereochemically pure dioxolane nucleoside analogues. The process includes the use of hydrolytic enzymes for separating β and α anomers from an anomeric mixture represented by formula (A) or formula (B) wherein W is benzyl or benzoyl; R1 is selected from the group consisting of C1-6 alkyl and C6-15 aryl.

  本发明提供了一种制备立体化学纯的二氧兰嘧啶核苷类似物的方法。该方法包括使用水解酶从由式(A)或式(B)表示的异构混合物中分离β和α异构体，其中W为苯甲基或苯甲酰基；R1选自由C1-6烷基和C6-15芳基组成的群。
• Use of cytidine derivatives for the treatment of leukaemia
  申请人：Shire Canada Inc.

  公开号：EP2138179A1

  公开（公告）日：2009-12-30

  The present invention provides a novel method for treating leukemia and more particularly acute myelogenous leukemia (AML) in a host comprising administering to the host a therapeutically effective amount of a compound having formula (I): wherein B is cytosine or 5-fluorocytosine and R is selected from the group comprising H, monophosphate, diphosphate, triphosphate, carbonyl substituted with a C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C6-10 aryl, and (a) wherein each Rc is independently selected from the group comprising H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl and an hydroxy protecting group; and wherein said compound is substantially in the form of the (-) enantiomer.

  本发明提供了一种治疗宿主白血病，尤其是急性髓性白血病（AML）的新方法，该方法包括向宿主施用治疗有效量的式(I)化合物：其中 B 是胞嘧啶或 5-氟胞嘧啶，R 选自包括 H、单磷酸盐、二磷酸盐、三磷酸盐、被 C1-6 烷基、C2-6 烯基、C2-6 炔基、C6-10 芳基取代的羰基和 (a) 其中每个 Rc 独立地选自包括 H、C1-6 烷基、C2-6 烯基、C2-6 炔基和羟基保护基团的基团；并且其中所述化合物基本上为 (-) 对映异构体形式。
• Method and compositions for the synthesis of dioxolane nucleosides with beta-configuration
  申请人：BIOCHEM PHARMA INC.

  公开号：US20020058670A1

  公开（公告）日：2002-05-16

  The present invention relates to methods and compositions for preparing biologically important nucleoside analogues containing 1,3-dioxolane sugar rings. In particular, this invention relates to the stereoselective synthesis of the beta (cis) isomer by glycosylating the base with an intermediate of formula (II) below a temperature of about −10° C. 1 wherein R 1 and L are as defined herein.

  本发明涉及制备含有 1,3-二氧戊环糖的生物重要核苷类似物的方法和组合物。特别是，本发明涉及通过在约-10℃以下的温度下用式（II）中间体糖基化碱基，立体选择性合成β（顺式）异构体。 1 其中 R 1 和 L 如本文所定义。