3'-deoxy-3'-thio-5'-O-(tert-butyldimethylsilyl)thymidine | 221012-47-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 3'-deoxy-3'-thio-5'-O-(tert-butyldimethylsilyl)thymidine
• 英文别名: TBDPS(-5)2-deoxy-D-eryPenf3SH(b)-thymin-1-yl；1-[(2R,4S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-sulfanyloxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 221012-47-1
• 化学式: C₂₆H₃₂N₂O₄SSi
• 分子量: 496.703
• InChiKey: MNTHTVQBIDTZHG-XPWALMASSA-N

物化性质

• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  68.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3'-deoxy-3'-thio-5'-O-(tert-butyldimethylsilyl)thymidine 在 四丁基氟化铵 、 氨 、 四氯化锡 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 126.0h， 生成 1-(3-S-β-D-ribofuranosyl-2,3-dideoxy-3-thio-β-D-ribofuranosyl)-thymine
  参考文献：
  名称：

  Incorporation of a S-glycosidic linkage into a glyconucleoside changes the conformational preference of both furanose sugars

  摘要：

  A glyconucleoside containing a thioglycoside linkage, namely 1-(3-S-beta-D-ribofuranosyl-2,3-dideoxy-3-thio-beta-D-ribofuranosyl)-thymine, has been prepared through condensation of a suitably protected derivative of 3'-thiothymidine with an activated ribose sugar. NMR has been used to study the conformation of the S-disaccharide and the unmodified O-disaccharide. A full pseudorotational analysis showed that for the S-disaccharide, the ribose and deoxy ribose sugars have a preference for the south and north pucker, respectively; which is the reverse of what is seen for the O-disaccharide. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.11.007
• 作为产物：
  描述：

  5'-O-tert-butyldiphenylsilylthymidine 在 sodium hydroxide 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 3'-deoxy-3'-thio-5'-O-(tert-butyldimethylsilyl)thymidine
  参考文献：
  名称：

  Incorporation of a S-glycosidic linkage into a glyconucleoside changes the conformational preference of both furanose sugars

  摘要：

  A glyconucleoside containing a thioglycoside linkage, namely 1-(3-S-beta-D-ribofuranosyl-2,3-dideoxy-3-thio-beta-D-ribofuranosyl)-thymine, has been prepared through condensation of a suitably protected derivative of 3'-thiothymidine with an activated ribose sugar. NMR has been used to study the conformation of the S-disaccharide and the unmodified O-disaccharide. A full pseudorotational analysis showed that for the S-disaccharide, the ribose and deoxy ribose sugars have a preference for the south and north pucker, respectively; which is the reverse of what is seen for the O-disaccharide. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.11.007

文献信息

• A novel thiol protecting group: A 2-thioquinoline sulfide as a masked sulfhydryl moiety
  作者：Jiancun Zhang、Mark D. Matteucci

  DOI：10.1016/s0040-4039(98)02694-x

  日期：1999.2

  2-Thioquinoline sulfide was developed as a masked sulfhydryl entity. It is introduced through facile S(N)2 displacement reactions and is stable to a variety of reaction conditions including acids, bases and nucleophiles. It is readily unmasked using the mild treatment of sodium cyanoborohydride in acetic acid. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Incorporation of a S-glycosidic linkage into a glyconucleoside changes the conformational preference of both furanose sugars
  作者：Joanne Buckingham、John A. Brazier、Julie Fisher、Richard Cosstick

  DOI：10.1016/j.carres.2006.11.007

  日期：2007.1

  A glyconucleoside containing a thioglycoside linkage, namely 1-(3-S-beta-D-ribofuranosyl-2,3-dideoxy-3-thio-beta-D-ribofuranosyl)-thymine, has been prepared through condensation of a suitably protected derivative of 3'-thiothymidine with an activated ribose sugar. NMR has been used to study the conformation of the S-disaccharide and the unmodified O-disaccharide. A full pseudorotational analysis showed that for the S-disaccharide, the ribose and deoxy ribose sugars have a preference for the south and north pucker, respectively; which is the reverse of what is seen for the O-disaccharide. (c) 2006 Elsevier Ltd. All rights reserved.