6-bromo-2,3-di-O-benzyl-L-ascorbic acid | 104040-10-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 6-bromo-2,3-di-O-benzyl-L-ascorbic acid
• 英文别名: 6-bromo-2,3-O,O-dibenzyl-L-ascorbic acid；(2R)-2-[(1R)-2-bromo-1-hydroxyethyl]-3,4-bis(phenylmethoxy)-2H-furan-5-one
• CAS: 104040-10-0
• 化学式: C₂₀H₁₉BrO₅
• 分子量: 419.272
• InChiKey: CRTITLAAUQOSIL-DLBZAZTESA-N

物化性质

• 沸点：
  675.5±55.0 °C(predicted)
• 密度：
  1.48±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-bromo-2,3-di-O-benzyl-L-ascorbic acid 在 sodium carbonate 作用下， 生成 2,3-di-O-benzyl-4-(5,6)-epoxy-L-ascorbic acid
  参考文献：
  名称：

  一些l-抗坏血酸衍生物的晶体结构、圆二色光谱和绝对构型

  摘要：

  摘要 通过 X 射线晶体学研究了具有 4-(5,6-环氧)- (4) 和 6-O-甲苯磺酰基- (8) 官能团的 l-抗坏血酸的手性 2,3-O,O-二苄基醚和圆二色性 (CD) 光谱。2,3-O,O-二苄基-5,6-异亚丙基-1-抗坏血酸(6) 和8 的立体结构通过X 射线晶体结构分析确定。4 和 8 的 CD 光谱与其合成前体 (2-3、5-7) 和 l-抗坏血酸 (1) 本身的 CD 光谱的比较，以及 6 和 8 的晶体结构允许推断4的绝对构型。因此，4中的手性原子C-4和C-5具有R和S构型，这与1的构型一致。

  DOI：

  10.1016/j.molstruc.2003.09.019
• 作为产物：
  描述：

  维生素 C 在 氢溴酸 、 potassium carbonate 作用下， 以 溶剂黄146 为溶剂， 生成 6-bromo-2,3-di-O-benzyl-L-ascorbic acid
  参考文献：
  名称：

  一些l-抗坏血酸衍生物的晶体结构、圆二色光谱和绝对构型

  摘要：

  摘要 通过 X 射线晶体学研究了具有 4-(5,6-环氧)- (4) 和 6-O-甲苯磺酰基- (8) 官能团的 l-抗坏血酸的手性 2,3-O,O-二苄基醚和圆二色性 (CD) 光谱。2,3-O,O-二苄基-5,6-异亚丙基-1-抗坏血酸(6) 和8 的立体结构通过X 射线晶体结构分析确定。4 和 8 的 CD 光谱与其合成前体 (2-3、5-7) 和 l-抗坏血酸 (1) 本身的 CD 光谱的比较，以及 6 和 8 的晶体结构允许推断4的绝对构型。因此，4中的手性原子C-4和C-5具有R和S构型，这与1的构型一致。

  DOI：

  10.1016/j.molstruc.2003.09.019

文献信息

• Design, synthesis and in vitro evaluation on HRPE cells of ascorbic and 6-bromoascorbic acid conjugates with neuroactive molecules
  作者：Stefano Manfredini、Silvia Vertuani、Barbara Pavan、Federica Vitali、Martina Scaglianti、Fabrizio Bortolotti、Carla Biondi、Angelo Scatturin、Puttur Prasad、Alessandro Dalpiaz

  DOI：10.1016/j.bmc.2004.07.043

  日期：2004.10

  Preliminary investigations allowed us to anticipate that conjugation of nipecotic acid with L-ascorbate (AA) gave a prodrug endowed with anticonvulsant activity in mice. In view of these results, and in order to get deepen insight into the molecular aspects at the base of the transport mechanism, a second generation of compounds, based on 6-bromo-6-deoxy-L-ascorbic acid (BrAA) as the carrier molecule was designed and synthesized. Effects of the chirality of the transported drug was also investigated on R- and S-nipecotic acid. Interaction and uptake modalities were evaluated in our in vitro model based on human retinal pigment epithelium cells (HRPE), which expresses the membrane L-ascorbic acid (AA) SVCT2 transporters. A remarkable increase on SVCT2 affinity was found going from AA to BrAA conjugates, that is, 11 (K-i = 1187 +/- 78 muM) versus 19 (K-i = 193 +/- 14 muM) and 12 (K-i = 39.8 +/- 3.2 muM) versus 20, (K-i = 7.4 +/- 0.8 muM). Taken together, these data are in agreement with our initial hypothesis on the possibility to achieve better affinities by conjugation with AA analogs, and also consent to hypothesize the presence of accessory interactions that may improve transporters recognition. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis and Antitumor Activities of Novel Pyrimidine Derivatives of 2,3-<i>O</i>,<i>O</i>-Dibenzyl-6-deoxy-<scp>l</scp>-ascorbic Acid and 4,5-Didehydro-5,6- dideoxy-<scp>l</scp>-ascorbic Acid
  作者：Silvana Raić-Malić、Draženka Svedružić、Tatjana Gazivoda、Andreja Marunović、Antonija Hergold-Brundić、Ante Nagl、Jan Balzarini、Erik De Clercq、Mladen Mintas

  DOI：10.1021/jm0009540

  日期：2000.12.1

  The new pyrimidine derivatives of 2,3-O,O-dibenzyl-6-deoxy-L-ascorbic acid (8-10) were synthesized by condensation of uracil and its 5-fluoro- and 5-trifluoromethyl-substituted derivatives with 4-(5,6-epoxypropyl)-2,3-O,O-dibenzyl-L-ascorbic acid (7), while pyrimidine derivatives of 4,5-didehydro-5,6-dideoxy-L-ascorbic acid (14-17) with free C-2' and C-3' hydroxy groups in the lactone ring were obtained by debenzylation of 11-13 with boron trichloride. Z-Configuration of the C4'=C5' double bond and position of the benzyl group in the lactone ring of 14 were deduced from their H-1 and C-13 NMR spectra and connectivities in COSY, ROESY, and HMBC spectra. The exact stereostructure of 13 was confirmed by its X-ray crystal structure analysis. Of all the compounds in the series, compound 16 containing a 5-fluoro-substituted uracil ring showed the most significant antitumor activities against murine leukemia L1210/0 (IC50 = 1.4 mug/mL), murine mammary carcinoma FM3A/0 (IC50 = 0.78 mug/mL), and, to a lesser extent, human T-lymphocyte cells Molt4/C8 (IC50 = 31.8 mug/mL) and CEM/0 cell lines (IC50 = 20.9 mug/mL).
• Crystal structures, circular dichroism spectra and absolute configurations of some l-ascorbic acid derivatives
  作者：Karlo Wittine、Tatjana Gazivoda、Marko Markuš、Draginja Mrvoš-Sermek、Antonija Hergold-Brundić、Mario Cetina、Dinko Žiher、Vesna Gabelica、Mladen Mintas、Silvana Raić-Malić

  DOI：10.1016/j.molstruc.2003.09.019

  日期：2004.1

  synthetic precursors (2–3, 5–7) and l -ascorbic acid (1) itself, as well as crystal structures of 6 and 8 permitted to deduce the absolute configuration of 4. Thus, the chiral atoms C-4 and C-5 in 4 have R and S configurations, which is consistent with the configuration of 1.

  摘要 通过 X 射线晶体学研究了具有 4-(5,6-环氧)- (4) 和 6-O-甲苯磺酰基- (8) 官能团的 l-抗坏血酸的手性 2,3-O,O-二苄基醚和圆二色性 (CD) 光谱。2,3-O,O-二苄基-5,6-异亚丙基-1-抗坏血酸(6) 和8 的立体结构通过X 射线晶体结构分析确定。4 和 8 的 CD 光谱与其合成前体 (2-3、5-7) 和 l-抗坏血酸 (1) 本身的 CD 光谱的比较，以及 6 和 8 的晶体结构允许推断4的绝对构型。因此，4中的手性原子C-4和C-5具有R和S构型，这与1的构型一致。