(2R,3S,4S)-6-Methoxy-2-methyl-tetrahydro-pyran-3,4-diol | 198011-31-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S)-6-Methoxy-2-methyl-tetrahydro-pyran-3,4-diol
• 英文别名: (2R,3S,4S)-6-methoxy-2-methyloxane-3,4-diol
• CAS: 198011-31-3
• 化学式: C₇H₁₄O₄
• 分子量: 162.186
• InChiKey: QNKOVWCOVLYPKR-RDCZQUQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  11
• 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：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-萘酚 、 (2R,3S,4S)-6-Methoxy-2-methyl-tetrahydro-pyran-3,4-diol 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以91%的产率得到(2R,3S,4S,6R)-6-(2-Hydroxy-naphthalen-1-yl)-2-methyl-tetrahydro-pyran-3,4-diol
  参考文献：
  名称：

  Aryl and Allyl C-Glycosidation Methods Using Unprotected Sugars

  摘要：

  Practical and highly stereoselective aryl and allyl C-glycosidation methods using unprotected sugars as glycosyl donors have been developed. Aryl C-glycosidations of several unprotected 2-deoxy sugars with phenol and naphthol derivatives by the combined use of trimethylsilyl trifluoromethanesulfonate (TMSOTf)-AgClO4 or TMSOTf exclusively gave the corresponding unprotected o-hydroxyaryl beta-C-glycosides which appear in many biologically attractive aryl C-glycoside antibiotics as the key subunit. On the other hand, allyl C-glycosidations of several unprotected glycals with allyltrimethylsilane by TMSOTf afforded the corresponding unprotected and 2,3-unsaturated allyl alpha-C-glycosides in high yields which are versatile synthetic intermediates for the syntheses of optically active natural products.

  DOI：

  10.1021/jo972146v
• 作为产物：
  描述：

  Corchorusoside A 在 盐酸 、 甲醇 作用下， 生成 甲基-Alpha-D-吡喃葡糖苷 、 bipindogenin 、 (2R,3S,4S)-6-Methoxy-2-methyl-tetrahydro-pyran-3,4-diol
  参考文献：
  名称：

  Corchorusosides A, B, C, D, and E, New Cardiotonic Oligoglycosides from the Seed of Corchorus olitorius L. (Moroheiya)

  摘要：

  The methanolic extract of the seeds of Corchorus olitorius L. (Moroheiya) was found to show inhibitory effect against Na+-K+-ATPase and positive inotropic activity in the guinea pig isolated atria. Through bioassay-guided separation from the methanolic extract, new cardenolide oligoglycosides called corchorusosides A, B, C, D, and E were isolated together with six known cardenolide oligoglycosides. The structures of new corchorusosides were determined on the basis of chemical and physicochemical evidence. All cardenolide oligoglycosides from the seeds showed potent inhibitory activity against Na+,K+-ATPase, which was equivalent to those of digitoxin and ouabain. The methanolic extract, glycoside fraction, and principal glycoside showed potent acute toxicity by intraperitoneal administration, whereas they showed little acute toxicity by oral administration. Furthermore, by means of HPLC quantitative analysis of the cardiotonic oligoglycosides, it was found that the glycosides mainly distributed in the seeds, while the edible parts such as fresh young leaves and stems contained only trace amount.

  DOI：

  10.3987/com-98-8146

文献信息

• Environmentally benign aryl C-glycosidations of unprotected sugars using montmorillonite K-10 as a solid acid
  作者：Kazunobu Toshima、Yasunobu Ushiki、Goh Matsuo、Shuichi Matsumura

  DOI：10.1016/s0040-4039(97)01724-3

  日期：1997.10

  Highly practical aryl C-glycosidations of unprotected 1-OMe and 1-OH sugars with phenol and naphthol derivatives were effectively realized using montmorillonite K-10 as an environmentally compatible solid acid in CHCl3 or H2O. (C) 1997 Elsevier Science Ltd.
• Aryl and Allyl <i>C</i>-Glycosidation Methods Using Unprotected Sugars
  作者：Kazunobu Toshima、Goh Matsuo、Toru Ishizuka、Yasunobu Ushiki、Masaya Nakata、Shuichi Matsumura

  DOI：10.1021/jo972146v

  日期：1998.4.1

  Practical and highly stereoselective aryl and allyl C-glycosidation methods using unprotected sugars as glycosyl donors have been developed. Aryl C-glycosidations of several unprotected 2-deoxy sugars with phenol and naphthol derivatives by the combined use of trimethylsilyl trifluoromethanesulfonate (TMSOTf)-AgClO4 or TMSOTf exclusively gave the corresponding unprotected o-hydroxyaryl beta-C-glycosides which appear in many biologically attractive aryl C-glycoside antibiotics as the key subunit. On the other hand, allyl C-glycosidations of several unprotected glycals with allyltrimethylsilane by TMSOTf afforded the corresponding unprotected and 2,3-unsaturated allyl alpha-C-glycosides in high yields which are versatile synthetic intermediates for the syntheses of optically active natural products.
• Corchorusosides A, B, C, D, and E, New Cardiotonic Oligoglycosides from the Seed of Corchorus olitorius L. (Moroheiya)
  作者：Masayuki Yoshikawa、Toshiyuki Murakami、Hiromi Shimada、Nobuyuki Fukada、Hisashi Matsuda、Yutaka Sashida、Johji Yamahara

  DOI：10.3987/com-98-8146

  日期：——

  The methanolic extract of the seeds of Corchorus olitorius L. (Moroheiya) was found to show inhibitory effect against Na+-K+-ATPase and positive inotropic activity in the guinea pig isolated atria. Through bioassay-guided separation from the methanolic extract, new cardenolide oligoglycosides called corchorusosides A, B, C, D, and E were isolated together with six known cardenolide oligoglycosides. The structures of new corchorusosides were determined on the basis of chemical and physicochemical evidence. All cardenolide oligoglycosides from the seeds showed potent inhibitory activity against Na+,K+-ATPase, which was equivalent to those of digitoxin and ouabain. The methanolic extract, glycoside fraction, and principal glycoside showed potent acute toxicity by intraperitoneal administration, whereas they showed little acute toxicity by oral administration. Furthermore, by means of HPLC quantitative analysis of the cardiotonic oligoglycosides, it was found that the glycosides mainly distributed in the seeds, while the edible parts such as fresh young leaves and stems contained only trace amount.