p-chlorophenyl 3,5-di-O-tert-butyldimethylsilyl-2-deoxy-2-fluoro-1-thio-β-D-arabinofuranoside | 916987-56-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-chlorophenyl 3,5-di-O-tert-butyldimethylsilyl-2-deoxy-2-fluoro-1-thio-β-D-arabinofuranoside
• CAS: 916987-56-9
• 化学式: C₂₃H₄₀ClFO₃SSi₂
• 分子量: 507.257
• InChiKey: DOPMNYYRUSXEDV-MHTWAQMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.91
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  p-chlorophenyl 3,5-di-O-tert-butyldimethylsilyl-2-deoxy-2-fluoro-1-thio-β-D-arabinofuranoside 在 MS 4 Angstroem 、 溴 作用下， 以 四氯化碳 为溶剂， 反应 1.5h， 生成 (2R,3S,4R,5R)-2-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-fluoro-tetrahydro-furan
  参考文献：
  名称：

  Synthesis of 2-deoxy-2-fluoro analogs of polyprenyl β-d-arabinofuranosyl phosphates

  摘要：

  Described is the synthesis of polyprenyl 2-deoxy-2-fluoro-beta-D-arabinofuranosyl phosphate derivatives, including an analog of decaprenyl P-D-arabinofuranosyl phosphate, the donor species used by the arabinosyltransferases involved in mycobacterial cell-wall biosynthesis. The targets were synthesized via a route involving the synthesis of a protected beta-D-arabinofuranosyl phosphate derivative, its coupling with a polyprenyl trichloroacetimidate, and then deprotection of the resulting product. The use of arabinofuranosyl phosphates with the monosaccharide hydroxyl groups protected as either silyl ethers or benzoate esters was explored. Although the coupling yields between the phosphate and polyprenyl trichloroacetimidates were comparable with either type of protecting group, access to the benzoyl-protected derivative was more efficient and therefore gave the products in higher overall yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.08.020
• 作为产物：
  描述：

  2-脱氧-1-溴-2-氟-3,5-二苯甲酰基-alpha-D-阿拉伯呋喃糖 在 咪唑 、 甲醇 、 氢氧化钾 、 四丁基溴化铵 、 sodium methylate 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.0h， 生成 p-chlorophenyl 3,5-di-O-tert-butyldimethylsilyl-2-deoxy-2-fluoro-1-thio-β-D-arabinofuranoside
  参考文献：
  名称：

  Synthesis of 2-deoxy-2-fluoro analogs of polyprenyl β-d-arabinofuranosyl phosphates

  摘要：

  Described is the synthesis of polyprenyl 2-deoxy-2-fluoro-beta-D-arabinofuranosyl phosphate derivatives, including an analog of decaprenyl P-D-arabinofuranosyl phosphate, the donor species used by the arabinosyltransferases involved in mycobacterial cell-wall biosynthesis. The targets were synthesized via a route involving the synthesis of a protected beta-D-arabinofuranosyl phosphate derivative, its coupling with a polyprenyl trichloroacetimidate, and then deprotection of the resulting product. The use of arabinofuranosyl phosphates with the monosaccharide hydroxyl groups protected as either silyl ethers or benzoate esters was explored. Although the coupling yields between the phosphate and polyprenyl trichloroacetimidates were comparable with either type of protecting group, access to the benzoyl-protected derivative was more efficient and therefore gave the products in higher overall yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.08.020