3-O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-1,2-O-isopropylidene-L-glycerol | 65751-66-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-1,2-O-isopropylidene-L-glycerol
• 英文别名: [(2R,3R,4S,5R,6S)-6-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]-3,4,5-tris(phenylmethoxy)oxan-2-yl]methanol
• CAS: 65751-66-8
• 化学式: C₃₃H₄₀O₈
• 分子量: 564.676
• InChiKey: YFMCLWQSHOSELM-UYIKLHEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  84.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-1,2-O-isopropylidene-L-glycerol 在 四氮唑 、 silver(II) bis(pyridine-2,6-dicarboxylate) 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 {2-[((S)-2-Azido-3-{(2-cyano-ethoxy)-[(2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-tetrahydro-pyran-2-ylmethoxy]-phosphoryloxy}-propoxy)-(2-cyano-ethoxy)-phosphoryloxy]-ethyl}-trimethyl-ammonium
  参考文献：
  名称：

  Synthesis and absolute configuration of a novel aminoglycoglycerolipid, species-specific major immunodeterminant of Mycoplasma fermentans

  摘要：

  In order to determine the absolute configuration of a novel aminoglycoglycerolipid isolated from Mycoplasma fermentans, the possible two diastereomers were stereoselectively synthesized by using (S)- and (R)-glycidols as the key building block. Their H-1-H-1-cosy spectra compared with those of the natural product allowed us to determine the absolute configuration of the glycolipid. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00191-4
• 作为产物：
  描述：

  丙酮 、 [(2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-((R)-1-oxiranylmethoxy)-tetrahydro-pyran-2-yl]-methanol 在 sodium methylate 、 cesium acetate 、 对甲苯磺酸 作用下， 生成 3-O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-1,2-O-isopropylidene-L-glycerol
  参考文献：
  名称：

  Synthesis and absolute configuration of a novel aminoglycoglycerolipid, species-specific major immunodeterminant of Mycoplasma fermentans

  摘要：

  In order to determine the absolute configuration of a novel aminoglycoglycerolipid isolated from Mycoplasma fermentans, the possible two diastereomers were stereoselectively synthesized by using (S)- and (R)-glycidols as the key building block. Their H-1-H-1-cosy spectra compared with those of the natural product allowed us to determine the absolute configuration of the glycolipid. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00191-4

文献信息

• Synthesis of 3-O-(6-deoxy-6-sulpho-α-<scp>D</scp>-glucopyranosyl)-1,2-di-O-hexadecanoyl-<scp>L</scp>-glycerol, ‘sulphoquinovosyl diglyceride’
  作者：Roy Gigg、Anna A. E. Penglis、Robert Conant

  DOI：10.1039/p19800002490

  日期：——
• Synthesis and absolute configuration of a novel aminoglycoglycerolipid, species-specific major immunodeterminant of Mycoplasma fermentans
  作者：Yoshihiro Nishida、Yusuke Takamori、Hiroshi Ohrui、Ineo Ishizuka、Kazuhiro Matsuda、Kazukiyo Kobayashi

  DOI：10.1016/s0040-4039(99)00191-4

  日期：1999.3

  In order to determine the absolute configuration of a novel aminoglycoglycerolipid isolated from Mycoplasma fermentans, the possible two diastereomers were stereoselectively synthesized by using (S)- and (R)-glycidols as the key building block. Their H-1-H-1-cosy spectra compared with those of the natural product allowed us to determine the absolute configuration of the glycolipid. (C) 1999 Elsevier Science Ltd. All rights reserved.