3,5-di-O-benzyl-2-deoxy-1,4-dithio-L-threo-pentofuranoside | 136737-52-5

• 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: 3,5-di-O-benzyl-2-deoxy-1,4-dithio-L-threo-pentofuranoside
• 英文别名: benzyl 3,6-di-O-benzyl-2-deoxy-1,5-dithio-L-threo-pentofuranoside；benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-α-threo-L-threo-pentofuranoside；benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-L-threo-pentafuranoside；(2S,3S)-5-benzylsulfanyl-3-phenylmethoxy-2-(phenylmethoxymethyl)thiolane
• CAS: 136737-52-5
• 化学式: C₂₆H₂₈O₂S₂
• 分子量: 436.639
• InChiKey: AJOOJPRYRSQRLM-NPGWBMRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  69.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-di-O-benzyl-2-deoxy-1,4-dithio-L-threo-pentofuranoside 在 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 三溴化硼 、 silver carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 生成 5-bromo-1-(2-deoxy-4-thio-α-L-threo-pentofuranosyl)uracil
  参考文献：
  名称：

  2'-Deoxy-4'-thio-L-threo-pentofuranosylpyrimidine 和-purine 核苷的合成和结构解析

  摘要：

  苄基 3,5-di-O-benzyl-2-deoxy-1,4-dithio-L-threo-pentofuranoside (13) 用作糖基供体，用于合成 4'-thio-L-threo-pentofuranosyluracil 衍生物 23 －29。相应的胞苷类似物 33 由 13 通过三唑基衍生物 31 制备。腺嘌呤和次黄嘌呤不与 13 反应。因此，13 转化为 1-O-乙酸酯 15，它是嘌呤碱基的足够反应性供体，产生4'-硫代-L-苏式-戊呋喃基嘌呤 36 和 37。在大多数情况下，可以获得脱保护的核苷类似物的纯端基异构体，其中三个适用于 X 射线结构分析。

  DOI：

  10.1002/1099-0690(200103)2001:6<1077::aid-ejoc1077>3.0.co;2-0
• 作为产物：
  描述：

  2-deoxy-D-ribose 在 吡啶 、 盐酸 、 四丁基碘化铵 、 sodium hydride 、 barium carbonate 、 sodium iodide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 120.5h， 生成 3,5-di-O-benzyl-2-deoxy-1,4-dithio-L-threo-pentofuranoside
  参考文献：
  名称：

  An improved synthesis of benzyl 3,5-di- O -benzyl-2-deoxy-1,4-dithio- d - erythro -pentofuranoside, an intermediate in the synthesis of 4′-thionucleosides

  摘要：

  DOI：

  10.1016/0008-6215(92)84165-o

文献信息

• The application of phenylmethanethiol and benzenethiol derivatives as odorless organosulfur reagents in the synthesis of thiosugars and thioglycosides
  作者：Jun-ya Hasegawa、Masahiro Hamada、Tetsuo Miyamoto、Kiyoharu Nishide、Tetsuya Kajimoto、Jun-ichi Uenishi、Manabu Node

  DOI：10.1016/j.carres.2005.07.011

  日期：2005.10

  p-octyloxyphenylmethanethiol and p-dodecylbenzenethiol were prepared as new odorless organosulfur reagents. Thiosugars and thioglycosides were synthesized using these reagents without encountering any malodorous procedures.

  制备了对位辛氧基苯甲硫醇和对十二烷基苯硫醇作为新的无味有机硫试剂。使用这些试剂合成了硫代糖精和硫糖苷，没有遇到任何恶臭的过程。
• The Synthesis and Biological Activity of Certain 4'-Thionucleosides
  作者：John Secrist、William Parker、Kamal Tiwari、Lea Messini、Sue Shaddix、Lucy Rose、L. Lee Bennett、John Montgomery

  DOI：10.1080/15257779508012449

  日期：1995.5.1

  Abstract Results are presented on the synthesis and biological activity of several types of 4′-thionucleosides as potential anticancer agents. Detailed studies on the mechanism of action of 4′-thiothymidine are also presented.

  摘要介绍了几种类型的4'-硫代核苷作为潜在抗癌剂的合成和生物学活性。还介绍了有关4'-硫代胸苷的作用机理的详细研究。
• Synthesis of 4-thiofuranoid 1,2-glycals and their application to stereoselective synthesis of 4′-thionucleosides
  作者：J.Allen Miller、Ashley W Pugh、G.Mustafa Ullah

  DOI：10.1016/s0040-4039(00)00366-x

  日期：2000.4

  Convenient one-pot procedures using iodine monochloride have been developed for the preparation of two 4-thio-1,2-glycals from readily available starting materials and for their beta-anomer selective conversion into 2'-iodo-4'-thionucleosides. Conditions for the reductive de-iodination of these iodonucleosides have been established and hence routes to a range of 2'-deoxy-4'-thionucleosides become feasible. (C) 2000 Elsevier Science Ltd. All rights reserved.
• The Synthesis and Biological Activity of 1-(2-Deoxy-4-Thio-α;-L-Threo-Pentofuranosyl)Thymine
  作者：Kamal N. Tiwari、John A. Montgomery、John A. Secrist

  DOI：10.1080/07328319308018554

  日期：1993.9

  The procedure of Huang and Hui (Nucleosides & Nucleotides 1993, 12, 139-147) was found to give benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-alpha-L-threo-pentofuranoside (6) rather than the claimed D-erythro isomer. This sugar was converted to an anomeric mixture of the thymine nucleosides. The mixture was separated and the alpha-anomer (alpha-10) was found to be cytotoxic, whereas the beta-anomer (beta-10) was inactive.
• Synthesis and Structural Elucidation of 2′-Deoxy-4′-thio-L-threo-pentofuranosylpyrimidine and -purine Nucleosides
  作者：Jörn Wirsching、Jürgen Voss、Gunadi Adiwidjaja、Anja Giesler、Jürgen Kopf

  DOI：10.1002/1099-0690(200103)2001:6<1077::aid-ejoc1077>3.0.co;2-0

  日期：2001.3

  (13) was used as glycosyl donor for the synthesis of 4′-thio-L-threo-pentofuranosyluracil derivatives 23−29. The corresponding cytidine analogue 33 was prepared from 13 via the triazolo derivative 31. Adenine and hypoxanthine did not react with 13. Therefore, 13 was transformed into the 1-O-acetate 15, which was a sufficiently reactive donor for the purine bases, yielding 4′-thio-L-threo-pentofuranosylpurines

  苄基 3,5-di-O-benzyl-2-deoxy-1,4-dithio-L-threo-pentofuranoside (13) 用作糖基供体，用于合成 4'-thio-L-threo-pentofuranosyluracil 衍生物 23 －29。相应的胞苷类似物 33 由 13 通过三唑基衍生物 31 制备。腺嘌呤和次黄嘌呤不与 13 反应。因此，13 转化为 1-O-乙酸酯 15，它是嘌呤碱基的足够反应性供体，产生4'-硫代-L-苏式-戊呋喃基嘌呤 36 和 37。在大多数情况下，可以获得脱保护的核苷类似物的纯端基异构体，其中三个适用于 X 射线结构分析。