methyl 2,3,4-tri-O-methyl-α-D-xylopyranoside | 7381-06-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-methyl-α-D-xylopyranoside
• 英文别名: (2S,3R,4S,5R)-2,3,4,5-tetramethoxyoxane
• CAS: 7381-06-8
• 化学式: C₉H₁₈O₅
• 分子量: 206.239
• InChiKey: OQFUMNZJTHPYPI-XAVMHZPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-methyl-β-D-xylopyranoside 、 methyl 2,3,4-tri-O-methyl-α-D-xylopyranoside 生成 (2R,3S,4R)-2,3,4,5-Tetramethoxy-5-phenylsulfanyl-pentan-1-ol
  参考文献：
  名称：

  GUINDON, Y.;ANDERSON, P. C., TETRAHEDRON LETT., 28,(1987) N 22, 2485-2488

  摘要：

  DOI：
• 作为产物：
  描述：

  甲基-Alpha-D-吡喃木糖 、 碘甲烷 在 甲醇 、 silver(l) oxide 作用下， 生成 methyl 2,3,4-tri-O-methyl-α-D-xylopyranoside
  参考文献：
  名称：

  Carruthers; Hirst, Journal of the Chemical Society, 1922, vol. 121, p. 2299,2305

  摘要：

  DOI：

文献信息

• Enantioselective Total Synthesis of (-)-Clavosolide A and B
  作者：Jung-Beom Son、Si-Nae Kim、Na-Yeong Kim、Min-Ho Hwang、Won-Sun Lee、Duck-Hyung Lee

  DOI：10.5012/bkcs.2010.31.03.653

  日期：2010.3.20

  Enantioselective total synthesis of (-)-clavosolide A and B was reported in full including the synthesis of proposed structure of (-)-clavosoldie A (1), revised structure of (-)-clavosoldie A (5), and revised structure of (-)-clavosoldie B (6). The relative and absolute stereochemistries of the natural products were confirmed unambiguously by comparing the optical rotation values and $^1H$ and $^13}C$ NMR spectra of them.

  完全报道了(-)-clavosolide A和B的对映选择性全合成，包括所提出的(-)-clavosolide A (1)结构的合成、修订后的(-)-clavosolide A (5)结构的合成以及修订后的(-)-clavosolide B (6)结构的合成。通过比较其旋光值和$^1H$及$^13}C$核磁共振谱，明确证实了这些天然产物的相对和绝对立体化学。
• New toxic metabolites from a mushroom, Hebeloma vinosophyllum. II. Isolation and structures of hebevinosides VI, VII, VIII, IX, X, and XI.
  作者：HARUHIRO FUJIMOTO、HIDEMI HAGIWARA、KUMIKO SUZUKI、MIKIO YAMAZAKI

  DOI：10.1248/cpb.35.2254

  日期：——

  Four new triterpene glycosides, hebevinosides VI, VII, VIII, and IX, whose common aglycone is 3β, 7β, 16β-trihydroxycucurbita-5, 24-diene (hydroxyhebevinogenin), have been isolated from the acetone extract of a poisonous mushroom, Hebeloma vinosophyllum, and deduced to have the structures of 3β, 7β, 16β-trihydroxycucurbita-5, 24-diene-3-Ο-β-D-xylopyranoside-16-O-β-D-glucopyranoside, 3β, 7β, 16β-trihydroxycucurbita-5, 24-diene-3-Ο-β-D-xylopyranoside-16-Ο- (4, 6-di-Ο-acetyl) -β-D-glucopyranoside, 3β, 7β, 16β-trihydroxycucurbita-5, 24-diene-3-Ο- (4-Ο-acetyl) -β-D-xylopyranoside-16-Ο- (4, 6-di-Ο-acetyl) -β-D-glucopyranoside, and 3β, 7β, 16β-trihydroxycucurbita-3-Ο-β-D-xylopyranoside, respectively. Two new glycosides, hebevinosides X and XI, whose common aglycone is 3β, 16, β-dihydroxy-7β-methoxycucurbita-5, 24-diene (methoxyhebevinogenin), have also been isolated from the aqueous methanolic extract of the mushroom in addition to hebevinosides I, II, III, IV, and V previously reported, and deduced to be 3β, 16β-dihydroxy-7β-methoxycucurbita-5, 24-diene-3-Ο-β-D-xylopyranoside-16-Ο-β-D-glucopyranoside and 3β, 16β-dihydroxy-7β-methoxycucurbita-5, 24-diene-3-Ο-β-D-xylopyranoside-16-Ο- (4, 6-di-Ο-acetyl) -β-D-glucopyranoside, respectively. Among these eleven hebevinosides, I, IV, V, X, and XI, whose common aglycone is methoxyhebevinogenin, have been proved to be artifacts formed from the genuine metabolites III, IX, II, VI, and VII, whose common aglycone is hydroxyhebevinogenin, during extraction of the mushroom with aqueous methanol, respectively, and VIII, whose aglycone is hydroxyhebevinogenin, has also been proved to be a genuine metabolite of this mushroom. The relationship between the structure and toxicity of hebevinosides was also investigated.

  四种新三萜苷，hebevinosides VI、VII、VIII 和 IX，其共同的甾体核心为 3β, 7β, 16β-三羟基南瓜烯-5, 24-二烯（羟基hebevinogenin），已从一种有毒蘑菇 Hebeloma vinosophyllum 的丙酮提取物中分离出来，推测其结构为 3β, 7β, 16β-三羟基南瓜烯-5, 24-二烯-3-Ο-β-D-木糖吡喃糖苷-16-O-β-D-葡萄糖吡喃糖苷、3β, 7β, 16β-三羟基南瓜烯-5, 24-二烯-3-Ο-β-D-木糖吡喃糖苷-16-O-(4, 6-二-O-乙酰)-β-D-葡萄糖吡喃糖苷、3β, 7β, 16β-三羟基南瓜烯-5, 24-二烯-3-Ο-(4-O-乙酰)-β-D-木糖吡喃糖苷-16-O-(4, 6-二-O-乙酰)-β-D-葡萄糖吡喃糖苷，以及 3β, 7β, 16β-三羟基南瓜烯-3-Ο-β-D-木糖吡喃糖苷，各自为。另有两种新苷类，hebevinosides X 和 XI，其共同的甾体核心为 3β, 16β-二羟基-7β-甲氧基南瓜烯-5, 24-二烯（甲氧基hebevinogenin），也已从该蘑菇的水甲醇提取物中分离出来，此外还有之前报道的 hebevinosides I、II、III、IV 和 V，推测分别为 3β, 16β-二羟基-7β-甲氧基南瓜烯-5, 24-二烯-3-Ο-β-D-木糖吡喃糖苷-16-O-β-D-葡萄糖吡喃糖苷和 3β, 16β-二羟基-7β-甲氧基南瓜烯-5, 24-二烯-3-Ο-β-D-木糖吡喃糖苷-16-O-(4, 6-二-O-乙酰)-β-D-葡萄糖吡喃糖苷。在这十一种 hebevinosides 中，I、IV、V、X 和 XI，其共同甾体核心为甲氧基hebevinogenin，已被证明是从真正代谢物 III、IX、II、VI 和 VII（其共同甾体核心为羟基hebevinogenin）在用水甲醇提取该蘑菇的过程中形成的人工代谢物，而 VIII（其甾体核心为羟基hebevinogenin）也已被证明是真正的代谢物。还研究了 hebevinosides 的结构与毒性之间的关系。
• A xylosylglucoside of xanthoxylin from sapium sebiferum root bark
  作者：Isao Kouno、Toshihiro Saishoji、Midori Sugiyama、Nobusuke Kawano

  DOI：10.1016/s0031-9422(00)86992-7

  日期：1983.1

  Abstract Besides four known compounds, a new xylosylglucoside of xanthoxylin was isolated from the root bark of Chinese tallow tree, Sapium sebiferum and identified as 2-acetyl-3,5-dimethoxyphenyl- O -β- D -xylopyranosyl-(1-6)-β- D -glucopyranoside.

  摘要 除四种已知化合物外，从中国牛油树Sapium sebiferum 的根皮中分离出一种新的xanthoxylin 木糖苷，鉴定为2-乙酰-3,5-二甲氧基苯基-O-β-D-吡喃木糖基-(1-6) -β-D-吡喃葡萄糖苷。
• Steroidal glycosides of Tribulus terrestris Linn
  作者：Shashi B. Mahato、Niranjan P. Sahu、Amar N. Ganguly、Kazumoto Miyahara、Toshio Kawasaki

  DOI：10.1039/p19810002405

  日期：——

  Besides β-sitosterol-β-D-glucoside and dioscin, two new steroidal glycosides, neohecogenin glucoside and tribulosin, isolated from the aerial part of Tribulus terrestris Linn. were respectively shown to be neohecogenin-3-O-β-D-glucopyranoside (2) and neotigogenin-3-O-β-D-xylopyranosyl(1→2)-[β-D-xylopyranosyl(1→3)]-β-D-glucopyranosyl(1→4)-[α-L-rhamnopyranosyl(1→2)]-β-D-galactopyranoside (7).

  除了β谷甾醇-β- d葡糖苷和薯蓣皂甙，两个新的甾体糖苷，neohecogenin葡糖苷和tribulosin，从地上部分分离蒺藜属。分别示出为neohecogenin -3- ö -β- d吡喃葡萄糖苷（2）和neotigogenin -3- ö -β- d -xylopyranosyl（1→2） - [β- d -xylopyranosyl（1→3）] - β- D-吡喃葡萄糖基（1→4）-[α- L-鼠李糖吡喃糖基（1→2）]-β- D-吡喃半乳糖苷（7）。
• Stereoelectronic effects in the ring cleavage of methyl glycopyranosides using dimethylboron bromide
  作者：Yvan Guindon、Paul C. Anderson

  DOI：10.1016/s0040-4039(00)95447-9

  日期：1987.1

  Treatment of methyl D-glycopyranosides with dimethylboron bromide followed by a nucleophile gives acyclic products resulting from selective cleavage of the ring carbon-oxygen bond. The results are rationalized based on stereoelectronic considerations.

  用二甲基溴化硼和亲核试剂处理甲基D-糖吡喃糖苷后，由于环碳-氧键的选择性切割而产生无环产物。根据立体电子因素对结果进行合理化。