methyl 2,3,4-tri-O-methyl-α-L-rhamnopyranoside | 35939-73-2

• 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-L-rhamnopyranoside
• 英文别名: methyl 2,3,4-tri-O-methylrhamnopyranoside；(2R,3R,4R,5S,6S)-2,3,4,5-tetramethoxy-6-methyloxane
• CAS: 35939-73-2
• 化学式: C₁₀H₂₀O₅
• 分子量: 220.266
• InChiKey: FHJGOJSYFDDBAA-SRQGCSHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  15
• 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-α-L-rhamnopyranoside 、 溶剂黄146 、 硫酸 生成 (3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-ol
  参考文献：
  名称：

  ROHR, JURGEN;ZEECK, AXEL, J. ANTIBIOTICS, 43,(1990) N, C. 1169-1178

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl-(O²-methyl-3,4-anhydro-6-deoxy-α-L-talopyranoside) 在 盐酸 、 甲醇 、 silver(l) oxide 作用下， 生成 methyl 2,3,4-tri-O-methyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  由甲基3：4-和2：3-脱水-6-脱氧-α-L-taloside的环氧化物的碱和还原性裂变产生的产物及其甲基化衍生物

  摘要：

  DOI：

  10.1039/jr9540002443

文献信息

• Regioselective methylation of methyl glycopyranosides with diazomethane in the presence of transition-metal chlorides and of boric acid
  作者：Evgeny V. Evtushenko

  DOI：10.1016/s0008-6215(99)00044-0

  日期：1999.3

  Abstract Partial methylation of the methyl pyranosides of a number of pentoses, hexoses, 6-deoxyhexoses, methyl uronates and their methyl ethers with diazomethane in the presence of transition-metal chlorides and boric acid was studied. It was found for methyl glycosides of pentoses and 6-deoxyhexoses that tin(II), antimony(III), and titanium(IV) chlorides as well as boric acid promoted substitution

  摘要研究了在过渡金属氯化物和硼酸存在下，许多戊糖，己糖，6-脱氧己糖，尿酸甲酯及其甲基醚的甲基吡喃糖苷与重氮甲烷的部分甲基化。发现戊糖和6-脱氧己糖的甲基糖苷中锡（II），锑（III）和钛（IV）氯化物以及硼酸主要促进OH-3的取代，但被铈（III）和锌的取代（II）观察到盐主要取代了OH-2。在所有情况下，甲基β-1-鼠李糖吡喃糖苷的甲基化表现出较高的OH-2反应性。在氯化锡（II），锑（III）和铈（III）的存在下，己糖甲基糖苷的甲基化反应主要产生了3-甲基醚。不参与进一步络合的3-甲基醚 积聚高达50-80％的反应混合物（95％至100％的单甲醚馏分）。建议用于许多糖的方便的甲基醚的合成。
• Steroid saponins and sapogenins of underground parts of Trillium kamtschaticum Pall. IV. Additional oligoglycosides of 18-norspirostane derivatives and other steroidal constituents.
  作者：NAOMICHI FUKUDA、NARIKO IMAMURA、EIKO SAITO、TOSIHIRO NOHARA、TOSHIO KAWASAKI

  DOI：10.1248/cpb.29.325

  日期：——

  Three oligoglycosides of 18-norspirostane derivatives, Ty-2, Ty-3, and Ty-4, along with two steroidal compounds, Tm and Tj, were isolated from the underground parts of Trillium kamtschaticum PALL. These five compounds and two other compounds, Th and Tz acetate, which had been obtained previously but remained unidentified, were characterized as follows. Ty-2, mp 235-240°(dec.), [α]D-110° : deapio-trillenoside A (II) (named trillenoside B). Ty-3, mp 182-185°(dec.), [α]D-98.7° : 3, 21-di-O-acetyl-24-epitrillenogenin 1-O-(2', 3', 4'-tri-O-acetyl-α-L-rha·pyr)-(1-2)-α-L-ara·pyranoside (IV) (epitrillenoside C-PA). Ty-4, mp 226-230°(dec.), [α]D-105°; 21-deoxytrillenoside A (VII) (deoxytrillenoside A). Tm, mp 326-329°(dec.), [α]D-99.4° : 24β-hydroxypennogenin (V). Tj, mp 205-212°(dec.), [α]D-66.5° : prototype compound (VIII) of pennogenin 3-O-β-chacotrioside. Th, mp 194-200°(dec.), [α]D-90° : prototype compound (IX) of pennogenin 3-O-α-L-rha·pyr-β-chacotrioside. Tz acetate : crude ecdysterone triacetate (X). This is the first report of the natural occurrence of these compounds, except for IX and X ; the occurrence of IV is particularly interesting. VIII and IX had been expected to coexist with the corresponding pennogenin glycosides.

  从延龄草地下部分分离得到3个18-去甲螺旋甾烷衍生物三糖甙Ty-2、Ty-3和Ty-4及2个甾体化合物Tm和Tj。以前得到的但是未被鉴定的2个甾体化合物Th和Tz乙酸酯也可被鉴定。其鉴定结果如下:Ty-2,熔点235-240°(分解),[α]_D-110°:异延龄草皂甙A (Ⅱ) (延龄草皂甙B)。Ty-3,熔点182-185°(分解),[α]_D-98.7°:3,21-二-O-乙酰基-24-表延龄皂甙元1-O-(2′, 3′, 4′-三-O-乙酰基-α-L-吡喃鼠李糖)-(1→2)-α-L-吡喃阿拉伯糖甙 (Ⅳ) (表延龄草皂甙C-PA)。Ty-4,熔点226-230°(分解),[α]_D-105°:21-去氧延龄草皂甙A (Ⅶ) (去氧延龄草皂甙A)。Tm,熔点326-329°(分解),[α]_D-99.4°:24β-羟基蚱蜢甾酮 (Ⅴ)。Tj,熔点205-212°(分解),[α]_D-66.5°:蚱蜢甾酮3-O-β-查可三糖甙原型化合物 (Ⅷ)。Th,熔点194-200°(分解),[α]_D-90°:蚱蜢甾酮3-O-α-L-吡喃鼠李糖-β-查可三糖甙原型化合物 (Ⅸ)。Tz乙酸酯:乙基蜕皮甾酮三乙酸酯粗品 (Ⅹ)。除了化合物Ⅸ、Ⅹ以外,其它化合物在自然界中的发现尚属首次。特别是化合物Ⅳ的出现引起了人们极大的兴趣。在此之前人们曾预测在相应的蚱蜢甾酮糖甙中共存Ⅷ和Ⅸ型化合物。
• Structure characterization of haemostatic diosgenin glycosides from paris polyphylia
  作者：James C.N. Ma、F.W. Lau

  DOI：10.1016/s0031-9422(00)81066-3

  日期：1985.1

  Abstract From Paris polyphylla var. chinensis Hare (Liliaceae), four diosgenin glycosides with haemostatic effects were isolated. The structure of the major component was elucidated by chemical and spectroscopic methods as 3-[α- L -rhamnopyranosyl(1 Rha → 2 Glu )]-[α- L -arabinofuranosyl(1 Ara → 4 Glu )]-β D -glucopyranosyl}-25( R )-spirost-5-en-3β-ol. This saponin was found to be identical to three

  摘要来自巴黎多叶变种。中华野兔（百合科），分离出四种具有止血作用的薯蓣皂苷。主要成分的结构通过化学和光谱方法阐明为 3-[α- L -rhamnopyranosyl(1 Rha → 2 Glu )]-[α- L -arabinofuranosyl(1 Ara → 4 Glu )]-β D -吡喃葡萄糖基}-25(R)-spirost-5-en-3β-ol。发现该皂苷与先前报道的三种最初被指定为其他结构的化合物相同，即来自多叶的主要成分、云南白药的主要细胞毒性成分，以及来自生长在喜马拉雅地区的多叶的多叶素 D .
• Studies on the constituents of the root of Polygala tenuifolia Willdenow. II. On the structures of onjisaponins A, B and E.
  作者：SEIICHI SAKUMA、JUNZO SHOJI

  DOI：10.1248/cpb.30.810

  日期：——

  The structures of three triterpenoidal saponins, onjisaponins A (1), B (2) and E (3), were determined on the basis of spectral and chemical evidence as presenegenin-(3)-β-D-glucopyranosido-(28)-2-O-[β-D-apio-D-furanosyl (1→3)] [β-D-galactopyranosyl (1→4)-β-D-xylopyranosyl (1→4)]-α-L-rhamnopyranosyl}-3-O-(α-L-rhamnopyranosyl)-4-O-(4'-methoxy-cinnamoyl)-β-D-fucopyranoside, presenegenin-(3)-β-D-glucopyranosido-(28)-2-O-[β-D-galactopyranosyl (1→4)-β-D-xylopyranosyl (1→4)-α-L-rhamnopyranosyl]-3-O-(α-L-rhamnopyranosyl)-4-O-(4'-methoxycinnamoyl)-β-D-fucopyranoside (=senegin III) and presenegenin- (3)-O-β-D-glucopyranosido-(28)-2-O-[β-D-galactopyranosyl (1→4)-β-D-xylopyranosyl (1→4)-α-L-rhamnopyranosyl]-4-O-(3', 4', 5'-trimethoxycinnamoyl)-β-D-fucopyranoside, respectively. The 13C nuclear magnetic resonance spectra of onjisaponins A, B, E and their derivatives were investigated and each carbon signal was assigned as shown in Table I.

  三种三萜皂苷的结构，即翁鸡皂苷A（1）、B（2）和E（3），是基于光谱和化学证据确定的，其结构分别为：presenegenin-(3)-β-D-glucopyranosido-(28)-2-O-[β-D-apio-D-furanosyl (1→3)] [β-D-galactopyranosyl (1→4)-β-D-xylopyranosyl (1→4)]-α-L-rhamnopyranosyl}-3-O-(α-L-rhamnopyranosyl)-4-O-(4'-methoxy-cinnamoyl)-β-D-fucopyranoside，presenegenin-(3)-β-D-glucopyranosido-(28)-2-O-[β-D-galactopyranosyl (1→4)-β-D-xylopyranosyl (1→4)-α-L-rhamnopyranosyl]-3-O-(α-L-rhamnopyranosyl)-4-O-(4'-methoxycinnamoyl)-β-D-fucopyranoside（=senegin III）和presenegenin-(3)-O-β-D-glucopyranosido-(28)-2-O-[β-D-galactopyranosyl (1→4)-β-D-xylopyranosyl (1→4)-α-L-rhamnopyranosyl]-4-O-(3', 4', 5'-trimethoxycinnamoyl)-β-D-fucopyranoside。对翁鸡皂苷A、B、E及其衍生物的13C核磁共振光谱进行了研究，并对每个碳信号进行了如表I所示的赋值。
• Triterpene and steroidal glycosides of the genus Melilotus and their genins. VI. Melilotoside A2 and adzukisaponin V from the roots of M. tauricus
  作者：G. V. Khodakov

  DOI：10.1007/s10600-013-0455-x

  日期：2013.1

  Two triterpene glycosides of the oleanane series, melilotoside A2 and previously known adzukisaponin V, were isolated from the roots of Melilotus tauricus (L.) Pall. (Fabaceae). The structures of the glycosides were proved based on chemical transformations. Melilotoside A2 had the structure soyasapogenol B 3-O-β-D-glucouronopyranoside; adzukisaponin V, soyasapogenol B 3-O-[α-L-rhamnopyranosyl-(1-2)-β-Dglucopyranosyl-(1-2)-β-D-glucuronopyranoside].

  从 Melilotus tauricus (L.) Pall.（豆科植物）的根中分离出了两种齐墩果烷系列的三萜苷，即 Melilotoside A2 和以前已知的 adzukisaponin V。(豆科）根中分离出来。这些苷的结构是通过化学转化得到证实的。Melilotoside A2 的结构为 soyasapogenol B 3-O-β-D-glucouronopyranoside; adzukisaponin V, soyasapogenol B 3-O-[α-L-rhamnopyranosyl-(1-2)-β-Dglucopyranosyl-(1-2)-β-D-glucuronopyranoside].