1,6-diacetyl-3,4-di-(acetoxymethyl)-2,5-O-methylene-D-mannitol | 5463-69-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,6-diacetyl-3,4-di-(acetoxymethyl)-2,5-O-methylene-D-mannitol
• 英文别名: O³,O⁴-bis-acetoxymethyl-O¹,O⁶-diacetyl-O²,O⁵-methanediyl-D-mannitol；O³,O⁴-Bis-acetoxymethyl-O¹,O⁶-diacetyl-O²,O⁵-methandiyl-D-mannit；1,6-Di-O-acetyl-3,4-bis-O-(acetoxymethyl)-2,5-O-methylene-D-mannitol；[(4R,5R,6R,7R)-5,6-bis(acetyloxymethoxy)-7-(acetyloxymethyl)-1,3-dioxepan-4-yl]methyl acetate
• CAS: 5463-69-4；18311-52-9；69257-55-2
• 化学式: C₁₇H₂₆O₁₂
• 分子量: 422.386
• InChiKey: MAZKRBGBNOYUSO-QBPKDAKJSA-N

物化性质

• 沸点：
  502.2±50.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  29
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1,6-diacetyl-3,4-di-(acetoxymethyl)-2,5-O-methylene-D-mannitol 在 吡啶 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 1,6-dipivaloyl-2,5-O-methylene-D-mannitol
  参考文献：
  名称：

  Synthesis of 1-O-alkyl-sn-glycerols and fluorescently labeled analogs from as precursor

  摘要：

  A new approach employing 2,5-O-methylene-D-Mannitol as precursor for the synthesis of naturally occurring and fluorescently labeled alkyl glycerols is described. From 2,5-O-methylene-D-mannitol, which was prepared according to the method of Ness et al. [1], 2,2-O-methylene-bis-(3-O-trityl)-sn-glycerol, the central product, was synthesized to an enantiomerically pure molecule in four steps. 1-O-hexadecyl-sn-glycerol was prepared by condensation of hexadecyl methanesulfonate with the central product and by subsequent detritylation and cleavage of the methylene bridge. From the alkyl glycerol the different lipid classes can be synthesized by well known strategies. To form fluorescently labeled analogs of alkyl glycerols the fluorescence marker 7-chloro-4-nitrobenzo-2-oxa-1,3-diazole (NBD-Cl) was linked with the omega-amino group of 1-O-(12-aminododecyl)-sn-glycerol. Therefore the central product was condensed with 12-N-t-BOC-aminododecyl methanesulfonate. The methylene bridge. the trityl groups and the BOC protection group were cleaved with boron trifluoride/methanol in one step. 1-O-(12-NBD-aminododecyl)-sn-glycerol is useful as a biochemical substrate to build up fluorescently labeled neutral lipids and phospholipids.

  DOI：

  10.1016/0009-3084(93)90036-3
• 作为产物：
  描述：

  乙酸酐 、 1,3:2,5:4,6-三-o-亚甲基-D-甘露糖醇 在 硫酸 、 溶剂黄146 作用下， 反应 0.25h， 以81%的产率得到1,6-diacetyl-3,4-di-(acetoxymethyl)-2,5-O-methylene-D-mannitol
  参考文献：
  名称：

  Synthesis of 1-O-alkyl-sn-glycerols and fluorescently labeled analogs from as precursor

  摘要：

  A new approach employing 2,5-O-methylene-D-Mannitol as precursor for the synthesis of naturally occurring and fluorescently labeled alkyl glycerols is described. From 2,5-O-methylene-D-mannitol, which was prepared according to the method of Ness et al. [1], 2,2-O-methylene-bis-(3-O-trityl)-sn-glycerol, the central product, was synthesized to an enantiomerically pure molecule in four steps. 1-O-hexadecyl-sn-glycerol was prepared by condensation of hexadecyl methanesulfonate with the central product and by subsequent detritylation and cleavage of the methylene bridge. From the alkyl glycerol the different lipid classes can be synthesized by well known strategies. To form fluorescently labeled analogs of alkyl glycerols the fluorescence marker 7-chloro-4-nitrobenzo-2-oxa-1,3-diazole (NBD-Cl) was linked with the omega-amino group of 1-O-(12-aminododecyl)-sn-glycerol. Therefore the central product was condensed with 12-N-t-BOC-aminododecyl methanesulfonate. The methylene bridge. the trityl groups and the BOC protection group were cleaved with boron trifluoride/methanol in one step. 1-O-(12-NBD-aminododecyl)-sn-glycerol is useful as a biochemical substrate to build up fluorescently labeled neutral lipids and phospholipids.

  DOI：

  10.1016/0009-3084(93)90036-3

文献信息

• Ness; Hann; Hudson, Journal of the American Chemical Society, 1943, vol. 65, p. 2218
  作者：Ness、Hann、Hudson

  DOI：——

  日期：——
• US4777293A
  申请人：——

  公开号：US4777293A

  公开（公告）日：1988-10-11