(2R,3R,4R)-1,3,4-Tris-benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-pentan-2-ol | 190968-26-4

• 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,3R,4R)-1,3,4-Tris-benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-pentan-2-ol
• CAS: 190968-26-4
• 化学式: C₄₂H₄₈O₅Si
• 分子量: 660.926
• InChiKey: DTGADKIPDZFUCW-MHEUVVKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.31
• 重原子数：
  48.0
• 可旋转键数：
  17.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R)-1,3,4-Tris-benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-pentan-2-ol 在 钯 、 pyridinium chlorochromate 作用下， 以 甲醇 、 甲酸 、 二氯甲烷 为溶剂， 生成 4-[(1S,2R)-3-(tert-Butyl-diphenyl-silanyloxy)-1,2-dihydroxy-propyl]-4-hydroxy-dihydro-furan-2-one
  参考文献：
  名称：

  A Short and Efficient Synthetic Process to Enantiomerically Pure (+)-Syributin 1

  摘要：

  For the synthesis of (+)-syributin 1 produced by bacteria which expresses the avrD gene, a simple and practical synthetic route is described in a short number of steps and high overall yield featuring the elaboration of D-arabinofuranose derivative.

  DOI：

  10.3987/com-97-7939
• 作为产物：
  描述：

  2,3,5-tri-O-benzyl-β-D-arabinofuranose 在 咪唑 、 sodium tetrahydroborate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,3R,4R)-1,3,4-Tris-benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-pentan-2-ol
  参考文献：
  名称：

  A Short and Efficient Synthetic Process to Enantiomerically Pure (+)-Syributin 1

  摘要：

  For the synthesis of (+)-syributin 1 produced by bacteria which expresses the avrD gene, a simple and practical synthetic route is described in a short number of steps and high overall yield featuring the elaboration of D-arabinofuranose derivative.

  DOI：

  10.3987/com-97-7939

文献信息

• Anomeric sugar boronic acid analogues as potential agents for boron neutron capture therapy
  作者：Daniela Imperio、Erika Del Grosso、Silvia Fallarini、Grazia Lombardi、Luigi Panza

  DOI：10.3762/bjoc.15.135

  日期：——

  of accelerators as neutron source, the access to new suitable agents for boron neutron capture therapy (BNCT) became a major need. Among many others, sugar boronic acids have recently attracted attention as boron carriers. Herein we report the synthesis and preliminary biological studies of two new sugar analogues containing a boronic acid at the anomeric position. The analogues were obtained by hydroboration

  在发展加速器作为中子源之后，获得用于硼中子俘获疗法（BNCT）的新的合适药物成为了主要需求。除其他外，糖硼酸作为硼载体最近引起了人们的注意。本文中，我们报道了在异头位置含有硼酸的两种新糖类似物的合成和初步生物学研究。通过适当的开链末端烯烃的氢硼化获得类似物，将其用水淬灭后，自发得到具有半缩醛样结构的环状硼酸。
• Synthesis of 2′,3″,4″-trisphosphate-containing analogs of adenophostin A
  作者：Nicole C.R. van Straten、Gijsbert A. van der Marel、Jacques H. van Boom

  DOI：10.1016/s0040-4020(97)00308-6

  日期：1997.5

  Adenophostin A analog 4 was prepared via trimethylsilyl trifluoromethanesulfonate (TMSOTf)-assisted glycosylation of (S)-6-N-diphenylacetyl-9-(2-tert-butyldiphenylsilyloxy-1-hydroxyprop-3-yl)-adenine (11) with trichloroacetimidate donor 12 to give dimer 13. Protective group manipulations on 13 followed by phosphitylation with N,N-diisopropyl-bis-[2-(methylsulfonyl)ethyl] phosphoramidite (17) and in situ oxidation gave, after deprotection, (25)-9-1-(alpha-D-glucopyranosyloxy 3,4-bisphosphate)-2-monophosphate-prop-3-yl}-adenine (4) Condensation of phosphoryloxymethyladenosine 25 with D-arabinitol derivative 21 under the agency of TMSOTf afforded methylene acetal 26. Protective group manipulations (--> 32), phosphorylation, and deprotection yielded 3'-O-(D-arabinitol-4-O-methylene 2,3-bisphosphate)-adenosine 2'-monophosphate (5), a methylene acetal-containing analog of adenophostin A. (C) 1997 Elsevier Science Ltd.