allyl O²,O³;O⁴,O⁶-bis-isopropylidene-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: allyl O²,O³;O⁴,O⁶-bis-isopropylidene-α-D-glucopyranoside
• 英文别名: (1R,2S,6R,7S,9R)-4,4,12,12-tetramethyl-7-prop-2-enoxy-3,5,8,11,13-pentaoxatricyclo[7.4.0.02,6]tridecane
• 化学式: C₁₅H₂₄O₆
• 分子量: 300.352
• InChiKey: OLFDWHBLAAGZGF-LBELIVKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  烯丙基-alpha-D-吡喃葡萄糖苷	1-O-allyl-α-D-glucopyranoside	7464-56-4	C9H16O6	220.222

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	allyl O3-tert-butyl-O4,O6-isopropylidene-α-D-glucopyranoside	219927-59-0	C16H28O6	316.395

反应信息

• 作为反应物：
  描述：

  甲基碘化镁 、 allyl O²,O³;O⁴,O⁶-bis-isopropylidene-α-D-glucopyranoside 以 乙醚 、 苯 为溶剂， 反应 1.5h， 以86%的产率得到allyl O³-tert-butyl-O⁴,O⁶-isopropylidene-α-D-glucopyranoside
  参考文献：
  名称：

  高度保护甘露糖胺的合成与反应

  摘要：

  高度保护的甘露糖胺衍生物由在C 2 位具有游离羟基的保护葡萄糖衍生物合成。研究了受保护的甘露糖胺衍生物的铟介导的烯丙基化。

  DOI：

  10.1002/jccs.200100151
• 作为产物：
  描述：

  allyl-α-D-gulopyranoside 生成 allyl O²,O³;O⁴,O⁶-bis-isopropylidene-α-D-glucopyranoside
  参考文献：
  名称：

  BARILI, PIER LUIGI;CATELANI, GIORGIO;COLONNA, FABRIZIA;MARRA, ALBERTO;CER+, CARBOHYDR. RES., 177,(1988) 29-41

  摘要：

  DOI：

文献信息

• Chelation-Assisted Regioselective C−O Bond Cleavage Reactions of Acetals by Grignard Reagents. A General Procedure for the Regioselective Synthesis of Protected Polyols Having One Free Hydroxy Group
  作者：Wen-Lung Cheng、Yeng-Jeng Shaw、Sue-Min Yeh、Puthuparampil P. Kanakamma、Yu-Huey Chen、Chuo Chen、Jia-Cheng Shieu、Shaang-Jyh Yiin、Gene-Hsiang Lee、Yu Wang、Tien-Yau Luh

  DOI：10.1021/jo981579a

  日期：1999.1.1

  Acetals containing a neighboring heteroatom react with the Grignard reagent in aromatic hydrocarbon solvents regioselectively. The auxiliary moiety can be hydroxy, alkoxy, or amino but not sulfur. Chelation plays a key role in directing the regioselectivity of this ring opening reaction. The reactions of acetonide derivatives of monosaccharides under these conditions afford the corresponding products having only one free hydroxy group at the specific position. Fully protected mannosamine derivative is prepared in good yield. The stereochemistry of the carbon center where auxiliary group is attached can be either syn or anti to the acetal oxygen moiety where cleavage of the C-O bond occurs. However, difference in reactivity has been found in the reaction of tris-acetonide of sorbitol with MeMgI. Regioselective ring opening of the acetal group at the anomeric carbon generates a hemiacetal which underwent further nucleophilic addition to furnish the corresponding alcohol stereoselectively.
• BARILI, PIER LUIGI;CATELANI, GIORGIO;COLONNA, FABRIZIA;MARRA, ALBERTO;CER+, CARBOHYDR. RES., 177,(1988) 29-41
  作者：BARILI, PIER LUIGI、CATELANI, GIORGIO、COLONNA, FABRIZIA、MARRA, ALBERTO、CER+

  DOI：——

  日期：——
• Synthesis and Reactions of Highly Protected Mannosamines
  作者：Jia-Cheng Smeu、Yeng-Jeng Shaw、Tien-Yau Luh

  DOI：10.1002/jccs.200100151

  日期：2001.12

  Highly protected mannosamine derivatives are synthesized from protected glucose derivatives having a free hydroxy group at C 2 position. Indium-mediated allylation of protected mannosamine derivatives is investigated.

  高度保护的甘露糖胺衍生物由在C 2 位具有游离羟基的保护葡萄糖衍生物合成。研究了受保护的甘露糖胺衍生物的铟介导的烯丙基化。