D-digitalose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-digitalose
• 英文别名: digitalose；Thevetose；(3R,4S,5S,6R)-4-methoxy-6-methyloxane-2,3,5-triol
• 化学式: C₇H₁₄O₅
• 分子量: 178.185
• InChiKey: OEKPKBBXXDGXNB-MSPRSRQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  D-digitalose 、 乙硫醇 以71%的产率得到O³-methyl-D-fucose-diethyldithioacetal
  参考文献：
  名称：

  A Convenient Synthesis of a Cardiac Sugar: “D-Digitalose”

  摘要：

  D-Digitalose (6-deoxy-3-O-methyl-D-galactose), a biologically important sugar that is found in some cardiac glycosides, was synthesized from D-galactose via 3-O-methyl-1,2,5-O-orthodichloroacetyl-alpha-D-galactofuranose.

  DOI：

  10.1080/07328303.2011.624285
• 作为产物：
  描述：

  1,2-O-[(S)-2,2,2-trichloroethane-1,1-diyl]-α-D-galactofuranose 在 吡啶 、 lithium aluminium tetrahydride 、 potassium tert-butylate 、 水 、 对甲苯磺酸 、 barium(II) oxide 作用下， 以 甲醇 、 乙醚 、 乙醇 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 170.0h， 生成 D-digitalose
  参考文献：
  名称：

  A Convenient Synthesis of a Cardiac Sugar: “D-Digitalose”

  摘要：

  D-Digitalose (6-deoxy-3-O-methyl-D-galactose), a biologically important sugar that is found in some cardiac glycosides, was synthesized from D-galactose via 3-O-methyl-1,2,5-O-orthodichloroacetyl-alpha-D-galactofuranose.

  DOI：

  10.1080/07328303.2011.624285

文献信息

• Teikaside A, a pregnane glycoside of Trachelospermum asiaticum.
  作者：FUMIKO ABE、TATSUO YAMAUCHI

  DOI：10.1248/cpb.29.416

  日期：——

  Teikaside A, one of the pregnane glycosides of Trachelospermum asiaticum (Apocynaceae), was isolated and its structure was determined to be 3-O-(β-D-digitalosyl)-20-O-(β-D-glucosyl-β-D-sarmentosyl)-3β, 17α, 20α-trihydroxy-5α-pregn-6-ene. In view of the structural similarity to the glycosides in Bei-Wujiapi, which are known to induce the potentiation of the nerve growth factor, similar physiological activity is expected in teikaside A.

  Teikaside A是亚洲爪哇藤（夹竹桃科）中的孕甾醇糖苷之一，经过分离并确定其结构为3-O-(β-D-地高辛糖基)-20-O-(β-D-葡萄糖基-β-D-梭子糖基)-3β, 17α, 20α-三羟基-5α-孕-6-烯。考虑到其与已知能够诱导神经生长因子增强的北乌药糖苷的结构相似，预计Teikaside A也具有类似的生理活性。
• Affinosides S-I-S-VIII, cardenolide glycosides with a usual glycosidic linkage, from Anodendron affine (Anodendron. IV).
  作者：FUMIKO ABE、TATSUO YAMAUCHI

  DOI：10.1248/cpb.31.1199

  日期：——

  Affinosides S-I-S-VIII were isolated from the caules and leaves of Anodendron affine DRUCE, and identified as glycosides of affinogenin C, D-I, and D-II, each having a single glycosidic linkage with D-digitalose, 6-deoxy-D-gulose, 4, 6-dideoxy-D-gulose, or D-glucose.

  从 Anodendron affine DRUCE 的茎和叶中分离出 Affinosides S-I-S-VIII，并鉴定为 Affinogenin C、D-I 和 D-II 的糖苷，各自与 D-数字糖、6-脱氧-D-古洛糖、6-脱氧-D-古洛糖、 4, 6-二脱氧-D-古洛糖，或D-葡萄糖。
• New pregnane glycosides from Caralluma hexagona Lavranos and their in vitro α-glucosidase and pancreatic lipase inhibitory effects
  作者：Akram A. Shalabi、Ali M. El Halawany、Mouchira A. Choucry、Fatma S. El-Sakhawy、Hiroyuki Morita、Dae-Won Ki、Essam Abdel-Sattar

  DOI：10.1016/j.phytol.2020.01.015

  日期：2020.4

  Three new pregnane glycosides in addition to four known compounds were isolated from the methylene chloride fraction of Caralluma hexagona Lavranos using bioassay-guided fractionation. The new compounds were identified as 12,20-di-O-benzoyl-3β,8β,12β,14β,20-pentahydroxy-(20R)-pregn-5-ene-3-O-β-d-glucopyranosyl-(1→4)-β-d-digitaloside (1), 3β,8β,14β,20-tetrahydroxy (20R)-pregn-5-ene-3-O-β-d-glucopyr

  使用生物测定指导的分馏方法，从六倍体Carallumahexaa Lavranos的二氯甲烷馏分中分离出三种新的孕烷糖苷。新的化合物，分别为12,20二ø -苯甲酰基-3 β，8 β，12 β，14 β，20-pentahydroxy-（20 - [R ）-孕-5-烯-3- ø - β - d -glucopyranosyl-（1→4） - β - d -digitaloside （1）， 3 β，8 β，14 β，20四羟基（20 - [R ）-孕-5-烯-3- ö- β - d -glucopyranosyl-（1→4） - ø - β - d -digitaloside -20- ø - β - d吡喃葡萄糖苷（2），3 β，8个β，14 β，20-四羟基（20 - [R） -孕-5-烯-3- ø - β - d -glucopyranosyl-（1→6） - ø - β - d -
• Perisesaccharides A–E, New Oligosaccharides from the Root Barks of<i>Periploca sepium</i>
  作者：Lei Wang、Zhi-Qi Yin、Ying Wang、Xiao-Qi Zhang、Yao-Lan Li、Wen-Cai Ye

  DOI：10.1055/s-0029-1240842

  日期：2010.6

  Five new oligosaccharides, named perisesaccharides A–E (1–5), were isolated from the root barks of Periploca sepium. Their structures were elucidated by NMR and HRESIMS data. The absolute configurations of these compounds were determined by a combination of X‐ray diffraction analysis, modified Mosher's method, circular dichroism spectroscopy, and acid hydrolysis. The boat conformation of oleandronic acid δ-lactone was reported for the first time.

  从 Periploca sepium 的根皮中分离出了五种新的寡糖，命名为 Perisesaccharides A-E（1-5）。核磁共振和 HRESIMS 数据阐明了它们的结构。这些化合物的绝对构型是通过 X 射线衍射分析、改进的莫舍尔法、圆二色光谱法和酸水解法测定的。首次报道了齐墩果酸δ-内酯的舟形构象。
• Cardiac glycosides from the seeds ofDigitalis ciliata
  作者：Ts. P. Sulakvelidze、É. P. Kemertelidze

  DOI：10.1007/bf00579173

  日期：1985.7