3,6-di-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose | 302917-21-1

• 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: 3,6-di-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose
• 英文别名: (1R)-1-[(3aR,5R,6R,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-phenylmethoxyethanol
• CAS: 302917-21-1
• 化学式: C₂₃H₂₈O₆
• 分子量: 400.472
• InChiKey: OSJRWERYMCTNBR-ZGJYDULXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,6-di-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose 在 甲醇 、 sodium methylate 、 氰化汞 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of the Nucleoside Moiety of Liposidomycins: Elucidation of the Pharmacophore of this Family of MraY Inhibitors

  摘要：

  Tunicamycins (TCMs) and liposidomycins (LPMs) are naturally occurring inhibitors of the bacterial translocase (MraY). Based on structure-activity relationship (SAR) studies, a molecular model has been proposed for their inhibitory mechanism. This study points out the importance of the nucleoside moiety of liposidomycins in the inhibition of MraY. A simplified molecule (I) based on the liposidomycin core structure has been synthesised and tested on MraY. The compound displayed a moderate inhibitory activity (IC50-50 mu M). The validation of the molecular model was then performed by synthesising higher homologues of I, containing an additional stereocentre in the 5' position (XIV and XV). In agreement with the prediction, only the (S) isomer XV showed significant activity against MraY (IC50=5 mu M). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00349-8
• 作为产物：
  描述：

  (3aR,5R,6R,6aR)-6-Benzyloxy-5-((R)-1,2-bis-benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole 在 chromium dichloride 、 lithium 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 11.0h， 以81%的产率得到3,6-di-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose
  参考文献：
  名称：

  单糖的区域选择性脱氧苄基化

  摘要：

  聚ø -benzylated糖正在使用的CrCl区域选择性脱苄基2在潮湿的EtOAc /的LiI。提出了一种预测性的三点协调模型。

  DOI：

  10.1016/s0040-4039(01)02306-1

文献信息

• Stereoselectivity in deoxygenation of 5-hydroxy-5-phosphinyl-hexofuranoses (α-hydroxyphosphonates)
  作者：Tadashi Hanaya、Ken-ichi Sugiyama、Heizan Kawamoto、Hiroshi Yamamoto

  DOI：10.1016/s0008-6215(03)00235-0

  日期：2003.7

  The addition of dimethyl phosphonate to six different hexofuranos-5-uloses in the presence of DBU, followed by esterification with methoxalyl chloride and then radical reduction, afforded 5-deoxy-5-dimethoxyphosphinyl-D- and L-hexofuranoses. The stereoselectivity of the deoxygenation and possible transition-state models are discussed. (C) 2003 Elsevier Ltd. All rights reserved.
• Regioselective de-O-benzylation of monosaccharides
  作者：J.R. Falck、D.K. Barma、Sylesh K. Venkataraman、Rachid Baati、Charles Mioskowski

  DOI：10.1016/s0040-4039(01)02306-1

  日期：2002.2

  Poly-O-benzylated sugars are regioselectively debenzylated using CrCl2/LiI in moist EtOAc. A predictive, three-point coordination model is proposed.

  聚ø -benzylated糖正在使用的CrCl区域选择性脱苄基2在潮湿的EtOAc /的LiI。提出了一种预测性的三点协调模型。
• Synthesis of the Nucleoside Moiety of Liposidomycins: Elucidation of the Pharmacophore of this Family of MraY Inhibitors
  作者：C. Dini、P. Collette、N. Drochon、J.C. Guillot、G. Lemoine、P. Mauvais、J. Aszodi

  DOI：10.1016/s0960-894x(00)00349-8

  日期：2000.8

  Tunicamycins (TCMs) and liposidomycins (LPMs) are naturally occurring inhibitors of the bacterial translocase (MraY). Based on structure-activity relationship (SAR) studies, a molecular model has been proposed for their inhibitory mechanism. This study points out the importance of the nucleoside moiety of liposidomycins in the inhibition of MraY. A simplified molecule (I) based on the liposidomycin core structure has been synthesised and tested on MraY. The compound displayed a moderate inhibitory activity (IC50-50 mu M). The validation of the molecular model was then performed by synthesising higher homologues of I, containing an additional stereocentre in the 5' position (XIV and XV). In agreement with the prediction, only the (S) isomer XV showed significant activity against MraY (IC50=5 mu M). (C) 2000 Elsevier Science Ltd. All rights reserved.