O²,O³-dibenzyl-O⁵,O⁶-isopropyliden-L-ascorbic acid | 122046-90-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O²,O³-dibenzyl-O⁵,O⁶-isopropyliden-L-ascorbic acid
• 英文别名: 2,3-di-O-benzyl-5,6-O-isopropylidene-D-isoascorbic acid；(2R)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-bis(phenylmethoxy)-2H-furan-5-one
• CAS: 122046-90-6
• 化学式: C₂₃H₂₄O₆
• 分子量: 396.44
• InChiKey: PBXJCPIRBBYFQV-RTBURBONSA-N

物化性质

• 沸点：
  624.8±55.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(2S)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-bis(phenylmethoxy)-2H-furan-5-one	185683-67-4	C23H24O6	396.44
  ——	(2R)-3,4-dibenzyloxy-2-[(1S)-1,2-dihydroxyethyl]-2H-furan-5-one	99663-32-8	C20H20O6	356.375

反应信息

• 作为反应物：
  描述：

  O²,O³-dibenzyl-O⁵,O⁶-isopropyliden-L-ascorbic acid 在 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 [4R-(R*,R*)]-α-Hydroxy-2,2-dimethyl-1,3-dioxolan-4-essigsaeure-(phenylmethyl)ester
  参考文献：
  名称：

  有机铝烷介导的抗坏血酸和异抗坏血酸衍生物的异构化

  摘要：

  当用三异丁基铝处理时，l-抗坏血酸2a和d-异抗坏血酸2b的衍生物部分发生差向异构化，生成l-异抗坏血酸ent - 2b，ent -10b或d-抗坏血酸ent - 2a ，ent -11a分别。保护基的完全除去是通过对亚甲基缩醛ent -10和ent- 11a进行氢解来实现的。该反应导致d抗坏血酸ENT -1a或1-异抗坏血酸ENT分别-1b。此外，四种丙酮化物2被臭氧分解，酯交换，最后催化氢化转化为苏糖醛和赤藓酸缩酮9。

  DOI：

  10.1016/0957-4166(96)00427-2
• 作为产物：
  描述：

  5,6-O-isopropylidene-D-isoascorbic acid 生成 O²,O³-dibenzyl-O⁵,O⁶-isopropyliden-L-ascorbic acid
  参考文献：
  名称：

  MATSUMURA, KOITI;SIMIDZU, JOSIAKI;SUGIXARA, JOSIXIRO

  摘要：

  DOI：

文献信息

• Saccharoascorbic acid esters, production and use thereof
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0295842A1

  公开（公告）日：1988-12-21

  A saccharoascorbic acid ester or a salt represented by the general formula of wherein R represents an organic residue of a molecular weight of 15-500, and OH has an S- or an R-configuration, and an electroconductive coating composition which contains such an ester or a salt thereof as an antioxidant together with an electroconductive metal powder.

  一种葡萄糖抗坏血酸酯或盐，其通式表示为其中R代表分子量为15-500的有机残基，OH具有S或R构型，并且一种电导涂层组合物，其含有此类酯或其盐作为抗氧化剂以及电导金属粉末。
• Design and efficient synthesis of novel ascorbyl conjugated peptide with high collagen biosynthesis stimulating effects
  作者：Ho-Il Choi、Heung-Jae Kim、Jong-Il Park、Eun-Ho Shin、Dong-Won Kim、Soung-Soo Kim

  DOI：10.1016/j.bmcl.2008.10.112

  日期：2009.4

  Collagen is critical for skin strength and elasticity, and its degradation leads to wrinkles that accompany aging. Based emphasis on the aesthetics, we tried to make a new compound that can highly stimulate collagen biosynthesis and synthesized ascorbyl conjugated peptide that is a complex form connected by succinoyl linker. We conducted several in vitro and in vivo experiments to identify if the compound has a potent activity, comparing to the ascorbic acid only for collagen biosynthesis. Our in vitro and in vivo result identified that ascorbyl conjugated peptide can stimulate collagen biosynthesis in human dermis and is assumably stable in the rat skin extracts. In conclusion, we strongly suggest that ascorbyl conjugated peptide can be used as a main ingredient for cosmetic products as well as wound healing agents. (C) 2008 Elsevier Ltd. All rights reserved.
• MATSUMURA, KOITI;SIMIDZU, JOSIAKI;SUGIXARA, JOSIXIRO
  作者：MATSUMURA, KOITI、SIMIDZU, JOSIAKI、SUGIXARA, JOSIXIRO

  DOI：——

  日期：——
• Synthesis, structural characterization and cytotoxic effect of 6-amino-6-deoxy-l-ascorbic acid derivatives
  作者：M Kralj、B Kojić-Prodić、Z Banić、M Grdiša、V Vela、B Šušković、K Pavelić

  DOI：10.1016/s0223-5234(96)80003-1

  日期：1996.1

  The synthesis, extended molecular modelling and cytotoxic effects of 6-amino-6-deoxy-L-ascorbic acid derivatives are described. For structure-function considerations, comparative conformational analysis was performed and X-ray structure analysis, molecular mechanics and molecular dynamics simulations were used in the search for the bioactive conformation(s). The cytotoxic effect of N,N-dimethyl-6-amino-6-deoxy-L-ascorbic acid on human tumour cell lines (Hep2, MiaPaCa2, HeLa) and on diploid human fibroblast (WI 38) was examined. The dimethylamino derivative of ascorbic acid expressed a stronger cytotoxic effect than ascorbic acid itself. This effect was cell-specific and dose dependent. The treatment of the cells with N,N-dimethyl-6-amino-6-deoxy-L-ascorbic acid probably resulted in apoptosis, evidenced by characteristic morphological changes and ladder DNA fragmentation. Apoptosis was not mediated by c-Myc or p53 proteins.
• Organoalane-mediated isomerization of ascorbic and isoascorbic acid derivatives
  作者：Josef Schachtner、Hans-Dietrich Stachel

  DOI：10.1016/0957-4166(96)00427-2

  日期：1996.11

  removal of the protecting groups is effected by hydrogenolysis of the benzylidene acetals ent-10 and ent-11a. This reaction leads to d-ascorbic acid ent-1a or l-isoascorbic acid ent-1b, respectively. Furthermore, the four acetonides 2 were converted by ozonolysis, transesterification and finally catalytic hydrogenation to the threonic and erythronic acid ketals 9.

  当用三异丁基铝处理时，l-抗坏血酸2a和d-异抗坏血酸2b的衍生物部分发生差向异构化，生成l-异抗坏血酸ent - 2b，ent -10b或d-抗坏血酸ent - 2a ，ent -11a分别。保护基的完全除去是通过对亚甲基缩醛ent -10和ent- 11a进行氢解来实现的。该反应导致d抗坏血酸ENT -1a或1-异抗坏血酸ENT分别-1b。此外，四种丙酮化物2被臭氧分解，酯交换，最后催化氢化转化为苏糖醛和赤藓酸缩酮9。