Methyl 3-Deoxy-3-fluoro-β-D-allopyranoside | 87585-98-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 3-Deoxy-3-fluoro-β-D-allopyranoside
• 英文别名: Methyl 3-deoxy-3-fluoro-beta-D-allopyranoside；(2R,3R,4R,5S,6R)-4-fluoro-2-(hydroxymethyl)-6-methoxyoxane-3,5-diol
• CAS: 87585-98-6
• 化学式: C₇H₁₃FO₅
• 分子量: 196.176
• InChiKey: CCAXOPTXMDCKMO-NYMZXIIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 3-Deoxy-3-fluoro-β-D-allopyranoside 在 OH- 作用下， 以 盐酸 、 水 为溶剂， 反应 8.0h， 以to afford the titled compound (2) (22.1 g) as a colorless syrup的产率得到3-deoxy-3-fluoro-D-allopyranose
  参考文献：
  名称：

  Processes for preparing 2'-deoxy-2'-fluorocoformycin and stereoisomers

  摘要：

  本发明通过经过多阶段的过程，通过3,5-二-O-苯甲酰基-2-脱氧-2-氟-.alpha.-和-.beta.-D-核糖溴化物合成了2'-脱氧-2'-氟可酶霉素和2'-脱氧-8-表-2'-氟可酶霉素。此外，根据本发明，从3,5-二-O-苯甲酰基-2-脱氧-2-氟-.alpha.-D-阿拉伯核糖溴化物开始，通过多阶段过程合成了2'-脱氧-2'-表-2'-氟可酶霉素和2'-脱氧-8,2'-双表-2'-氟可酶霉素。这四种2'-氟可酶霉素衍生物是新化合物，并且对腺苷脱氨酶具有高的酶抑制活性。特别是，这些新化合物是有用的物质，因为它们具有上述高酶抑制活性，对急性淋巴细胞白血病具有治疗作用。此外，还获得了多种中间体作为新化合物，这些中间体对于合成上述新的2'-氟可酶霉素衍生物是有用的。

  公开号：

  US05773607A1
• 作为产物：
  描述：

  Methyl 3-Deoxy-3-fluoro-6-O-trityl-β-D-allopyranoside 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 5.0h， 以43%的产率得到Methyl 3-Deoxy-3-fluoro-β-D-allopyranoside
  参考文献：
  名称：

  Fluorinated carbohydrates. 2. Selective fluorination of gluco- and mannopyranosides. Use of 2-D NMR for structural assignments

  摘要：

  DOI：

  10.1021/jo00172a054

文献信息

• Processes for preparing 2'-deoxy-2'-fluorocoformycin and stereoisomers
  申请人：Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai

  公开号：US05773607A1

  公开（公告）日：1998-06-30

  2'-Deoxy-2'-fluorocoformycin and 2'-deoxy-8-epi-2'-fluorocoformycin are synthesized in this invention through a multi-stage process via 3,5-di-O-benzoyl-2-deoxy-2-fluoro-.alpha.- and -.beta.-D-ribofuranosyl bromides. Further, according to this invention, 2'-deoxy-2'-epi-2'-fluorocoformycin and 2'-deoxy-8,2'-diepi-2'-fluorocoformycin are synthesized by a multi-stage process starting from 3,5-di-O-benzoyl-2-deoxy-2-fluoro-.alpha.-D-arabinofuranosyl bromide. These four 2'-fluoro derivatives of coformycin are novel compounds and have high enzyme-inhibitory activities against adenosine deaminase. In particular, these novel compounds are useful substances which exhibit therapeutic effects on acute lymphocytic leukemias due to their high enzyme-inhibitory activities above-mentioned. In addition, a variety of intermediates are obtained as novel compounds which are useful for the synthesis of the aforesaid novel 2'-fluoro derivatives of coformycin.

  本发明通过经过多阶段的过程，通过3,5-二-O-苯甲酰基-2-脱氧-2-氟-α-和-β-D-核糖溴代物合成了2'-脱氧-2'-氟可复霉素和2'-脱氧-8-表-2'-氟可复霉素。此外，根据本发明，通过从3,5-二-O-苯甲酰基-2-脱氧-2-氟-α-D-阿拉伯核糖溴代物开始的多阶段过程，合成了2'-脱氧-2'-表-2'-氟可复霉素和2'-脱氧-8,2'-二表-2'-氟可复霉素。这四种2'-氟可复霉素衍生物是新的化合物，并且对腺苷脱氨酶具有高的酶抑制活性。特别是，这些新化合物是有用的物质，由于其上述高酶抑制活性，对急性淋巴细胞白血病具有治疗效果。此外，还获得了多种中间体作为新的化合物，这些中间体对于合成上述新的2'-氟可复霉素衍生物是有用的。
• 2'-DEOXY-2'-FLUOROCOFORMYCIN AND STEREOISOMERS THEREOF
  申请人：ZAIDAN HOJIN BISEIBUTSU KAGAKU KENKYU KAI

  公开号：EP0643069A1

  公开（公告）日：1995-03-15

  2'-Deoxy-2'-fluorocoformycin and 2'-deoxy-8-epi-2'-fluorocoformycin have now been synthesized by a multistage reaction via 3,5-di-O-benzoyl-2-deoxy-2-fluoro-α- and -β-D-ribofuranosyl bromide. Also 2'-deoxy-2'-epi-2'-fluorocoformycin and 2'-deoxy-8,2'-diepi-2'-fluorocoformycin have been synthesized from 3,5-di-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranosyl bromide by a multistage reaction. These four 2'-fluorocoformycin derivatives are novel compounds and have a potent enzyme inhibiting activity against adenosine deaminase. In particular, they are useful for treating acute lymphocytic leukemia in virtue of the above activity. Other novel compounds also obtained include various intermediates useful for the synthesis of the above derivatives.

  2'-Deoxy-2'-fluorocoformycin 和 2'-deoxy-8-epi-2'-fluorocoformycin 现已通过 3,5-di-O-benzoyl-2-deoxy-2-fluoro-α- 和 -β-D-ribofuranosyl bromide 的多级反应合成。此外，3,5-二-O-苯甲酰基-2-脱氧-2-氟-α-D-阿拉伯呋喃糖基溴化物通过多级反应合成了 2'-deoxy-2'-epi-2'-fluorocoformycin 和 2'-deoxy-8,2'-diepi-2'-fluorocoformycin 。这四种 2'-氟甲酰霉素衍生物是新型化合物，对腺苷脱氨酶具有强效的酶抑制活性。由于具有上述活性，它们特别适用于治疗急性淋巴细胞白血病。此外，还获得了其他新型化合物，包括用于合成上述衍生物的各种中间体。
• A process for the preparation of 2'-deoxy-2'-halocoformycins or stereoisomers thereof
  申请人：ZAIDAN HOJIN BISEIBUTSU KAGAKU KENKYU KAI

  公开号：EP0794194B1

  公开（公告）日：2001-12-12
• Method for Optimizing Post-Translational Modifications on Recombinant Proteins
  申请人：LESZCYNIECKA Magdalena

  公开号：US20160340706A1

  公开（公告）日：2016-11-24

  A method for optimizing post-translational modifications of recombinant proteins expressed in living cells is described. More particularly, a method for modulation of host proteins in living cells that control PTMs on recombinant proteins is described that has particularly useful applications in developing manufacturing process changes or in biosimilar development. The goal of this modulation is to produce a recipe for production of a recombinant protein in the new process or in the biosimilar that will produce a targeted PTM profile in the resulting protein product. In the method one or more modulators are selected, as from a modulator library, which affect the activity of host proteins. These modulators are added to media during production such that the resulting product matches the PTMs of the reference product. The ideal set of modulators and their concentrations are identified through a unique iterative process and the combined modulators and their concentrations constitute a recipe for growth media for the production of said recombinant protein. The methodology to obtain such a recipe described herein may then be used in many applications, such as optimizing new batches of recombinant protein drugs, developing biosimilar or bio-better drugs.
• A METHOD FOR DEVELOPMENT OF RECOMBINANT PROTEINS WITH FINGERPRINT LIKE SIMILARITY TO THE REFERENCE PRODUCT
  申请人：STC Biologics, Inc.

  公开号：US20180180626A1

  公开（公告）日：2018-06-28

  The present invention relates to the methods of developing recombinant proteins with a fingerprint like similarity to the reference product or the originator. The method is particularly useful in the development of biosimilar products. This method can also be used to establish comparability during the manufacturing process change for the originator products. Hie methods described herein are used to obtain a recipe for the production of a biosimilar product or a recombinant protein using a process that may be different from the original but that yields a recombinant protein that has fingerprint level of similarity to the reference product. The methods described herein can also used to obtain a fingerprinting analysis package for a biosimilar that can be submitted to regulatory agency for abbreviated biosimilar approval. While currently available analytical methods can identify and quantitate specific modifications on a recombinant, protein, no methods currently exist to measure and determine the concentration of product variants in a complex: mixture. The analytical methods described herein provide for identification and quantitation of the modifications of the recombinant proteins and of product variants in a complex mixture by utilizing various in silico computational approaches to transform analytical data and derive product variant distribution.