2-脱氧-alpha-d-核糖1-磷酸二(环己基胺)

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-脱氧-alpha-d-核糖1-磷酸二(环己基胺)
• 英文名称: bis(cyclohexylamine) 2-deoxy-α-D-ribosyl-1-phosphate
• 英文别名: α-D-2′-deoxyribofuranose-1-O-phosphate bis(cyclohexylammonium) salt；O¹-phosphono-α-D-erythro-2-deoxy-pentofuranose; compound with cyclohexylamine；O¹-Phosphono-α-D-erythro-2-desoxy-pentofuranose; Verbindung mit Cyclohexylamin；2-deoxy-α-D-ribose 1-phosphate bis(cyclohexylamine) salt；2'-deoxyribose 1-phosphate di(monocyclohexylammonium) salt；cyclohexanamine;[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl] dihydrogen phosphate
• 化学式: C₅H₁₁O₇P*2C₆H₁₃N
• 分子量: 412.464
• InChiKey: PJYWCLQUAQQXBV-KYWOWLQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.16
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  142.47
• 氢给体数：
  5.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-脱氧-alpha-d-核糖1-磷酸二(环己基胺) 在 Dowex-50 Na+ 作用下， 以 水 为溶剂， 反应 0.5h， 以96%的产率得到α-D-2′-deoxyribofuranose-1-O-phosphate disodium salt
  参考文献：
  名称：

  酶法合成2-脱氧核糖1-磷酸和核糖1磷酸及随后的核苷制备

  摘要：

  我们提供了一种从7-Me-Guo和7-Me-dGuo制备Rib-p和dRib-p的新型酶促方法。在存在PNP的情况下，7-Me-Guo和7-Me-dGuo的几乎不可逆的磷酸分解可确保起始核苷定量转化为异构纯α-Rib-p和α-dRib-p。分离和纯化后，Rib-p和dRib-p的收率为74–96％。

  DOI：

  10.1002/ejoc.201901454
• 作为产物：
  描述：

  bis(cyclohexylamine) 3',5'-O-bis(4-chlorobenzoyl)-2-deoxy-α-D-ribosyl-1-phosphate 在 环己胺 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以85%的产率得到2-脱氧-alpha-d-核糖1-磷酸二(环己基胺)
  参考文献：
  名称：

  First Stereoselective Synthesis of 2-Deoxy-α-d-ribosyl-1-phosphate:  Novel Application of Crystallization-Induced Asymmetric Transformation

  摘要：

  A first stereoselective synthesis of bis(cyclohexylamine) 2-deoxy-alpha-D-ribosyl-1-phosphate has been achieved. The synthesis features a key crystallization-induced asymmetric transformation (AT) to generate a desired alpha-anomer in 99% yield at a 98.8:1.2 ratio of alpha/beta.

  DOI：

  10.1021/jo025793h

文献信息

• Method for producing a pyrimidine nucleoside compound and a new pyrimidine nucleoside compound
  申请人：Araki Tadashi

  公开号：US20050074857A1

  公开（公告）日：2005-04-07

  A method for producing a pyrimidine nucleoside compound includes reacting a sugar phosphate and pyrimidine base derivative using an enzyme having cytosine nucleoside phosphorylase activity, the pyrimidine base derivative being represented by general formula (I): (wherein R1 represents an amino group that may be replaced with an acyl group having an alkyl group of 1 to 3 carbon atoms or an alkyl group of 1 to 3 carbon atoms, an alkyl group of 1 to 3 carbon atoms, or a thiol group; R2 represents an amino group, a thiol group, a hydroxyl group, or a hydrogen atom; R3 represents an alkyl group of 1 to 3 carbon atoms that may be replaced with a hydroxyl group, an amino group, or a hydrogen atom; R4 represents a hydroxyl group or a hydrogen atom; when R1 is an amino group, when R2 is a hydroxyl group, and when R4 is a hydrogen atom; R3 is neither an alkyl group of 1 to 3 carbon atoms nor a hydrogen atom).

  生产嘧啶核苷化合物的方法包括使用具有胞嘧啶核苷化酶活性的酶，通过反应糖磷酸和嘧啶碱基衍生物来实现，其中嘧啶碱基衍生物由通用式(I)表示：（其中R1代表一个氨基，可以被具有1至3个碳原子的烷基或1至3个碳原子的烷基，1至3个碳原子的烷基或硫醇基替代；R2代表一个氨基，硫醇基，羟基或氢原子；R3代表1至3个碳原子的烷基，可以被羟基，氨基或氢原子替代；R4代表羟基或氢原子；当R1是氨基时，当R2是羟基时，当R4是氢原子时；R3既不是1至3个碳原子的烷基也不是氢原子）。
• Enzymatic Synthesis of 2-Deoxyribose 1-Phosphate and Ribose 1 Phosphate and Subsequent Preparation of Nucleosides
  作者：Irina V. Kulikova、Mikhail S. Drenichev、Pavel N. Solyev、Cyril S. Alexeev、Sergey N. Mikhailov

  DOI：10.1002/ejoc.201901454

  日期：2019.11.10

  Rib‐p and dRib‐p starting from 7‐Me‐Guo and 7‐Me‐dGuo. Practically irreversible phosphorolysis of 7‐Me‐Guo and 7‐Me‐dGuo in the presence of PNP ensures the quantitative transformation of starting nucleosides to anomerically pure α‐Rib‐p and α‐dRib‐p. Rib‐p and dRib‐p are obtained with 74–96 % yields after isolation and purification.

  我们提供了一种从7-Me-Guo和7-Me-dGuo制备Rib-p和dRib-p的新型酶促方法。在存在PNP的情况下，7-Me-Guo和7-Me-dGuo的几乎不可逆的磷酸分解可确保起始核苷定量转化为异构纯α-Rib-p和α-dRib-p。分离和纯化后，Rib-p和dRib-p的收率为74–96％。
• First Stereoselective Synthesis of 2-Deoxy-α-<scp>d</scp>-ribosyl-1-phosphate:  Novel Application of Crystallization-Induced Asymmetric Transformation
  作者：Hironori Komatsu、Hirokazu Awano

  DOI：10.1021/jo025793h

  日期：2002.7.1

  A first stereoselective synthesis of bis(cyclohexylamine) 2-deoxy-alpha-D-ribosyl-1-phosphate has been achieved. The synthesis features a key crystallization-induced asymmetric transformation (AT) to generate a desired alpha-anomer in 99% yield at a 98.8:1.2 ratio of alpha/beta.