methyl 3,4-di-O-methyl-L-arabinopyranoside | 95783-94-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4-di-O-methyl-L-arabinopyranoside
• 英文别名: methyl 3,4-di-O-methyl-arabinopyranoside；methyl 2,4-di-O-methylarabinopyranoside；methyl 3,4-di-O-methylarabinopyranoside；(3R,4R,5S)-2,4,5-trimethoxyoxan-3-ol
• CAS: 95783-94-1
• 化学式: C₈H₁₆O₅
• 分子量: 192.212
• InChiKey: VXOPRCAXQLGBIS-SZVWITLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (3R,4S,5S,6R)-2-[(3R,4S,5S,6R)-2-[(2S,3R,4S,5R)-6-[(3R,4S,5S)-4,5-dihydroxy-2-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-16-yl]oxyoxan-3-yl]oxy-4,5-dihydroxy-2-methyloxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-3-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol 生成 methyl 3,4-di-O-methyl-L-arabinopyranoside
  参考文献：
  名称：

  KINTYA, P. K.;DEGTYAREVA, L. P., XIMIYA PRIROD. SOED.,(1989) N, S. 139-140

  摘要：

  DOI：

文献信息

• Saponin and sapogenol. XXXVIII. Structure of soyasaponin A2, a bisdesmoside of soyasapogenol A, from soybean, the seeds of Glycine max Merrill.
  作者：ISAO KITAGAWA、MASAYUKI SAITO、TOSHIO TANIYAMA、MASAYUKI YOSHIKAWA

  DOI：10.1248/cpb.33.598

  日期：——

  Two new bisdesmosides of soyasapogenol A (1), named soyasaponin A1 and soyasaponin A2 (7), were isolated from soybean, the seeds of Glycine max MERRILL, together with the known soyasaponins I (4), II (5), and III (6). By employing a photochemical degradation method, which is a selective cleavage method for the glucuronide linkage in oligoglycosides, and on the bases of spectral analyses and chemical reactions, the structure of soyasaponin A2 was elucidated as 3-O-[β-D-galactopyranosyl (1→2)-β-D-glucuronopyranosyl]-22-O-[β-D-glucopyranosyl (1→3)-α-L-arabinopyranosyl] soyasapogenol A (7).

  从大豆（Glycine max MERRILL的种子）中分离出两种新的大豆皂醇A（1）的双糖苷，命名为大豆皂苷A1和大豆皂苷A2（7），以及已知的大豆皂苷I（4）、II（5）和III（6）。通过采用光化学降解方法，这是一种针对寡糖苷中葡萄糖醛酸键的选择性断裂方法，并基于光谱分析和化学反应，确定了大豆皂苷A2的结构为3-O-[β-D-半乳糖吡喃糖基（1→2）-β-D-葡萄糖醛酸吡喃糖基]-22-O-[β-D-葡萄糖吡喃糖基（1→3）-α-L-阿拉伯糖吡喃糖基]大豆皂醇A（7）。
• The structure of prosapogenin obtained from the saponin of Gleditsia japonica
  作者：Takao Konoshima、Hiroyuki Fukushima、Hideo Inui、Keiko Sato、Tokunosuke Sawada

  DOI：10.1016/0031-9422(81)85233-8

  日期：1981.1

  Abstract Prosapogenin was obtained by alkaline hydrolysis of Gleditsia saponin GS-C (echinoeystic acid 3, 28-O-bisdesmoside), a new triterpenoid saponin isolated from Gleditsia japoinica. Prosapogenin was shown on the basis of chemical and physicochemical data to be echinocystic acid 3-O-β- d -xylopyranosyl-(1–2)-α- l -arabinopyranosyl-(1–6)-β- d -glucopyranoside.

  摘要 Prosapogenin 是通过皂苷 GS-C（棘皮酸 3, 28-O-bisdesmoside）碱水解获得的，该皂苷是从皂角中分离得到的一种新的三萜皂苷。根据化学和物理化学数据显示，前皂苷元是棘囊酸 3-O-β-d-吡喃木糖基-(1-2)-α-l-阿拉伯吡喃糖基-(1-6)-β-d-吡喃葡萄糖苷。
• 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。
• Studies on the constituents of Clematis species. IV. On the saponins of the root of Clematis chinensis Osbeck. IV.
  作者：HARUHISA KIZU、TSUYOSHI TOMIMORI

  DOI：10.1248/cpb.30.859

  日期：——

  Four triterpenoid prosapogenins named CP7a, CP8a, CP9a and CP10a have been isolated from the alkaline hydrolysate of the crude saponin obtained from the root of Clematis chinensis OSBECK. On the basis of chemical and physicochemical evidence, they were characterized as follows : CP7a (I), oleanolic acid 3-O-β-D-glucopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside ; CP8a (VI), hederagenin 3-O-β-D-glucopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside ; CP9a (XI), oleanolic acid 3-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside ; CP10a (XIII), hederagenin 3-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→4)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside.

  从以威灵仙根部的粗皂苷经过碱性水解后的水解产物中，分离得到了4个三萜皂苷元，分别命名为CP7a、CP8a、CP9a和CP10a。基于化学和物理化学证据，它们被鉴定如下：CP7a（I）为齐墩果酸3-O-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃木糖基-(1→3)-α-L-吡喃鼠李糖基-(1→2)-α-L-吡喃阿拉伯糖苷；CP8a（VI）为常春藤苷元3-O-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃木糖基-(1→3)-α-L-吡喃鼠李糖基-(1→2)-α-L-吡喃阿拉伯糖苷；CP9a（XI）为齐墩果酸3-O-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃木糖基-(1→3)-α-L-吡喃鼠李糖基-(1→2)-α-L-吡喃阿拉伯糖苷；CP10a（XIII）为常春藤苷元3-O-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃木糖基-(1→3)-α-L-吡喃鼠李糖基-(1→2)-α-L-吡喃阿拉伯糖苷。
• Studies on the constituents of Leguminous plants. VII. The structure of triterpenoid saponins from fruits of Gymnocladus chinensis Baillon.
  作者：TAKAO KONOSHIMA、TOKUNOSUKE SAWADA、TAKEATSU KIMURA

  DOI：10.1248/cpb.32.4833

  日期：——

  Three triterpenoid saponins, gymnocladus saponins A (12), B (18) and C (20), were isolated from the fruits of Gymnocladus chinensis BAILLON (Leguminosae). On the basis of chemical and physicochemical evidence, these saponins were characterized as 2β, 23-dihydroxy-3-O-[α-L-arabinopyranosyl (1→6)-β-D-glucopyranosyl] acacic acid 28, 21-lactone (12), 2β, 23-dihydroxy-3-O-[β-D-glucopyranosyl (1→2)-β-D-glucopyranosyl] acacic acid 28, 21-lactone (18) and 2β, 23-dihydroxy-3-O-[β-D-xylopyranosyl (1→2)-α-L-arabinopyranosyl (1→6)-β-D-glucopyranosyl] acacic acid 28, 21-lactone (20).

  从中华金雀花（Gymnocladus chinensis BAILLON，豆科）果实中分离出三种三萜皂苷，分别是金雀花皂苷A (12)、B (18)和C (20)。根据化学和物理化学的证据，这些皂苷被表征为：2β, 23-二羟基-3-O-[α-L-阿拉伯糖吡喃糖（1→6）-β-D-葡萄糖吡喃糖] 酸性28, 21-内酯 (12)；2β, 23-二羟基-3-O-[β-D-葡萄糖吡喃糖（1→2）-β-D-葡萄糖吡喃糖] 酸性28, 21-内酯 (18)；和2β, 23-二羟基-3-O-[β-D-木糖吡喃糖（1→2）-α-L-阿拉伯糖吡喃糖（1→6）-β-D-葡萄糖吡喃糖] 酸性28, 21-内酯 (20)。