1-O-cetyl-2,4:5,6-di-O-isopropylidene-1-C-phenyl-D-glycero-D-ido-hexitol | 141882-83-9

• 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: 1-O-cetyl-2,4:5,6-di-O-isopropylidene-1-C-phenyl-D-glycero-D-ido-hexitol
• 英文别名: 1-O-Acetyl-2,4:5,6-di-O-isopropylidene-1-C-phenyl-D-glycero-D-ido-hexitol；[(R)-[(4R,5R,6S)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-hydroxy-2,2-dimethyl-1,3-dioxan-4-yl]-phenylmethyl] acetate
• CAS: 141882-83-9
• 化学式: C₂₀H₂₈O₇
• 分子量: 380.438
• InChiKey: IJPDVEZRRCCNQT-CWQOZTLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-O-cetyl-2,4:5,6-di-O-isopropylidene-1-C-phenyl-D-glycero-D-ido-hexitol 在 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 2,4-O-isopropylidene-1-C-phenyl-D-glycero-D-ido-hexitol
  参考文献：
  名称：

  （ - ） - goniofufurone和（ - ） - 8-立体控制合成外延-goniofufurone

  摘要：

  天然goniofufurone的绝对构型和8-外延-goniofufurone被示出为2和4由它们的对映异构体的无歧义的合成分别1和3从D-甘油基-D-庚-heptono-γ内酯7涉及的分子内迈克尔反应如关键步骤。容易从d-甘油-d - gugu-庚酮-γ-内酯得到的二醇6已通过六个顺序反应（乙酰化，水解，脱乙酰基，乙二醇裂解，Wittig反应和水解）转化为γ-内酯5进行了分子内迈克尔反应生成（-）-goniofufurone 1。同样，单乙酸酯12的反应产生（-）-8-表位-呋喃酮呋喃酮3。

  DOI：

  10.1016/s0040-4020(01)89441-2
• 作为产物：
  描述：

  2,4:5,6-Di-O-isopropylidene-D-glucose 、 乙酸酐 、 phenylmagnesium bromide 在 吡啶 、 4-二甲氨基吡啶 作用下， 生成 1,3-di-O-acetyl-2,4:5,6-di-O-isopropylidene-1-C-phenyl-D-glycero-D-gulo-hexitol 、 1-O-cetyl-2,4:5,6-di-O-isopropylidene-1-C-phenyl-D-glycero-D-ido-hexitol
  参考文献：
  名称：

  Stereoselective syntheses of 2,4:5,6-di-O-isopropylidene-1 -C-phenyl-D-glycero-D-ido-hexitol and 2,4:5,6-di-O-isopropylidene-1 -C-phenyl-D-glycero-D-gulo-hexitol fromD-glycero-D-gulo-heptono-γ-lactone. X-Ray structure of 1 -O-acetyl-2,4:5,6-di-O-isopropylidene-1-C-phenyl-D-glycero-D-ido-hexitol

  摘要：

  D-glycero-D-gulo-Heptonolactone has been converted by three consecutive reactions (acetonation, reduction and glycol cleavage reaction) into 2,4:5,6-di-O-isopropylidene-D-glucose which with phenylmagnesium bromide gave preponderantly 2,4:5,6-di-O-isopropylidene-1-C-phenyl-D-glycero-D-ido-hexitol 5. 2,4:5,6-Di-O-isopropylidene-1-C-phenyl-D-glycero-D-gulo-hexitol 6 has been obtained from 5 via an oxidation-reduction sequence. The structure of 5 has been confirmed by X-ray crystallographic analysis of its 1-O-acetyl-derivative 12.

  DOI：

  10.1039/p19920000887

文献信息

• Stereoselective syntheses of (–)-goniotriol and (–)-8-acetylgoniotriol from<scp>D</scp>-glycero-<scp>D</scp>-gulo-heptono-γ-lactone
  作者：Tony K. M. Shing、Zhao-Hui Zhou、Thomas C. W. Mak

  DOI：10.1039/p19920001907

  日期：——

  cero-D-gulo-hexitol 11 has been transformed via a sequence involving selective hydrolysis, deacetylation, glycol cleavage oxidation, and Wittig reaction into (Z)-methyl 4,6-O-isopropylidene-7-C-phenyl-L-gluco-hept-2-enonate 14 which with DBU provided (Z)-5,7-O-isopropylidene-8-C-phenyl-L-gluco-hept-3-enono-δ-lactone 16 from which (–)-goniotriol 1 and (–)-8-acetylgoniotriol 2 can be obtained readily

  1- ø -乙酰基2,4：5,6-二- ö异亚丙基-1- Ç苯基d -甘油基- d - IDO -hexitol 6通过三个连续的反应已被转换（选择性deacetonation，乙二醇氧化裂解（和Wittig反应）转化为（Z）-甲基7 - O-乙酰基-4,6 - O-异亚丙基-7 - C-苯基-D-基-庚基-2-enote 9，它与碱性甲醇一起生成2-脱氧- 4,6- O-异亚丙基-3- O-甲基-7- C-苯基-D-甘油基-大号- IDO -heptono-δ内酯10。X射线晶体学分析证实了10的结构。1,3-二- ø -乙酰基2,4：5,6-二- ö异亚丙基-1- Ç苯基d -甘油基- d -庚-hexitol 11已经转变经由涉及选择性水解的序列，脱乙酰化，乙二醇裂解氧化，Wittig反应成（ż） -甲基4,6- Ô异亚丙基-7- ç苯基大号-葡糖-用DBU提供的（h）-庚2-烯酸酯14（Z）-5