[(2R,3S,5R)-3-(4-chlorobenzoyl)oxy-5-phosphonooxyoxolan-2-yl]methyl 4-chlorobenzoate | 354823-29-3

• 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: [(2R,3S,5R)-3-(4-chlorobenzoyl)oxy-5-phosphonooxyoxolan-2-yl]methyl 4-chlorobenzoate
• CAS: 354823-29-3
• 化学式: C₁₉H₁₇Cl₂O₉P
• 分子量: 491.218
• InChiKey: KZPIWIBVBURNIV-GVDBMIGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R)-3-(4-chlorobenzoyl)oxy-5-phosphonooxyoxolan-2-yl]methyl 4-chlorobenzoate 在 purine nucleoside phosphorylase 作用下， 生成 2'-脱氧鸟苷
  参考文献：
  名称：

  LARGE-SCALE MANUFACTURING OF ALL FOUR 2′-DEOXYNUCLEOSIDES VIA NOVEL STRATEGIES INCLUDING A CHEMO-ENZYMATIC PROCESS

  摘要：

  A chemical synthesis of 2-deoxyribose-1-phosphate 2 and its enzymatic conversion into purine 2'-deoxynucleosides (dNus) are shown. Besides the chemoenzymatic process for purine dNus, a modified process for practical dC preparation is also established. Consequently, a series of practical manufacturing processes of all four dNus have been realized via novel strategies.

  DOI：

  10.1081/ncn-100002539
• 作为产物：
  描述：

  1-氯-2-脱氧-3,5-二-O-对氯苯甲酰基-D-核糖 在 磷酸 作用下， 生成 [(2R,3S,5R)-3-(4-chlorobenzoyl)oxy-5-phosphonooxyoxolan-2-yl]methyl 4-chlorobenzoate
  参考文献：
  名称：

  LARGE-SCALE MANUFACTURING OF ALL FOUR 2′-DEOXYNUCLEOSIDES VIA NOVEL STRATEGIES INCLUDING A CHEMO-ENZYMATIC PROCESS

  摘要：

  A chemical synthesis of 2-deoxyribose-1-phosphate 2 and its enzymatic conversion into purine 2'-deoxynucleosides (dNus) are shown. Besides the chemoenzymatic process for purine dNus, a modified process for practical dC preparation is also established. Consequently, a series of practical manufacturing processes of all four dNus have been realized via novel strategies.

  DOI：

  10.1081/ncn-100002539

文献信息

• Process for selectively producing 1-phosphorylated sugar derivative anomer and process for producing nucleoside
  申请人：——

  公开号：US20020193314A1

  公开（公告）日：2002-12-19

  A desired isomer is selectively prepared by phosphorolyzing and isomerizing an anomer mixture of a 1-phosphorylated saccharide derivative while crystallizing one of the isomers to displace the equilibrium. Furthermore, using the action of a nucleoside phosphorylase, a nucleoside is prepared from the 1-phosphorylated saccharide derivative obtained and a base with improved stereoselectivity and a higher yield. This process is an anomer-selective process for preparing a 1-phosphorylated saccharide derivative and a nucleoside.

  通过磷酸解和异构化1-磷酸化糖衍生物的环式异构体混合物，有选择性地制备所需的异构体，同时通过结晶其中一种异构体以移动平衡。此外，利用核苷酸磷酸化酶的作用，从获得的1-磷酸化糖衍生物和一种改善立体选择性和更高产率的碱基中制备核苷酸。该过程是用于制备1-磷酸化糖衍生物和核苷酸的环式选择性过程。
• Selective process for producing an anomer of a 1-phosphorylated saccharide derivative and process for producing a nucleoside
  申请人：Komatsu Hironori

  公开号：US20060094869A1

  公开（公告）日：2006-05-04

  A desired isomer is selectively prepared by phosphorolyzing and isomerizing an anomer mixture of a 1-phosphorylated saccharide derivative while crystallizing one of the isomers to displace the equilibrium. Furthermore, using the action of a nucleoside phosphorylase, a nucleoside is prepared from the 1-phosphorylated saccharide derivative obtained and a base with improved stereoselectivity and a higher yield. This process is an anomer-selective process for preparing a 1-phosphorylated saccharide derivative and a nucleoside.

  通过磷酸解和异构化1-磷酸化糖衍生物的异构体混合物，有选择性地制备所需的异构体，并结晶其中一种异构体以移动平衡。此外，利用核苷酸磷酸化酶的作用，从所得的1-磷酸化糖衍生物和碱基中制备核苷，具有改善的立体选择性和更高的产量。该过程是一种选择性异构过程，用于制备1-磷酸化糖衍生物和核苷。
• PROCESS FOR SELECTIVELY PRODUCING 1-PHOSPHORYLATED SUGAR DERIVATIVE ANOMER AND PROCESS FOR PRODUCING NUCLEOSIDE
  申请人：Mitsui Chemicals, Inc.

  公开号：EP1178051A2

  公开（公告）日：2002-02-06

  A desired isomer is selectively prepared by phosphorolyzing and isomerizing an anomer mixture of a 1-phosphorylated saccharide derivative while crystallizing one of the isomers to displace the equilibrium. Furthermore, using the action of a nucleoside phosphorylase, a nucleoside is prepared from the 1-phosphorylated saccharide derivative obtained and a base with improved stereoselectivity and a higher yield. This process is an anomer-selective process for preparing a 1-phosphorylated saccharide derivative and a nucleoside.

  通过对 1-磷酸化糖衍生物的异构体混合物进行磷酸化和异构化，选择性地制备所需的异构体，同时使其中一种异构体结晶以取代平衡。此外，在核苷磷酸化酶的作用下，还可以用获得的 1-磷酸化糖衍生物和碱制备核苷，立体选择性更高，产率也更高。该工艺是制备 1-磷酸化糖衍生物和核苷的同分异构体选择性工艺。
• US7038039B2
  申请人：——

  公开号：US7038039B2

  公开（公告）日：2006-05-02
• LARGE-SCALE MANUFACTURING OF ALL FOUR 2′-DEOXYNUCLEOSIDES VIA NOVEL STRATEGIES INCLUDING A CHEMO-ENZYMATIC PROCESS
  作者：Hironori Komatsu、Hirokazu Awano、Hiroharu Tanikawa、Kiyoshi Itou、Ichirou Ikeda

  DOI：10.1081/ncn-100002539

  日期：2001.3.31

  A chemical synthesis of 2-deoxyribose-1-phosphate 2 and its enzymatic conversion into purine 2'-deoxynucleosides (dNus) are shown. Besides the chemoenzymatic process for purine dNus, a modified process for practical dC preparation is also established. Consequently, a series of practical manufacturing processes of all four dNus have been realized via novel strategies.