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methyl 2,3,4-tri-O-methyl-β-D-xylopyranoside | 2876-85-9

中文名称
——
中文别名
——
英文名称
methyl 2,3,4-tri-O-methyl-β-D-xylopyranoside
英文别名
Methyl 2,3,4-tri-O-methylxylopyranoside;(2R,3R,4S,5R)-2,3,4,5-tetramethoxyoxane
methyl 2,3,4-tri-O-methyl-β-D-xylopyranoside化学式
CAS
2876-85-9
化学式
C9H18O5
mdl
——
分子量
206.239
InChiKey
OQFUMNZJTHPYPI-BZNPZCIMSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

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

安全信息

  • 海关编码:
    2932999099

SDS

SDS:fb35e238df4ea9c2dc2e95d7e4de3704
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上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
    —— Methyl 4-O-methyl-β-D-xylopyranoside 58918-59-5 C7H14O5 178.185
    —— Methyl 2-O-methyl-β-D-xylopyranoside 7381-12-6 C7H14O5 178.185
    甲基-β-D-吡喃木糖苷 methyl-β-D-xylopyranoside 612-05-5 C6H12O5 164.158
    D-吡喃木糖 D-Xylose 10257-31-5 C5H10O5 150.131
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量
    —— 2,3,4-tri-O-methyl-D-xylose 1130-67-2 C8H16O5 192.212

反应信息

  • 作为反应物:
    描述:
    methyl 2,3,4-tri-O-methyl-β-D-xylopyranoside盐酸 作用下, 以 为溶剂, 反应 10.0h, 生成 2,3,4-tri-O-methyl-D-xylono-1,5-lactone
    参考文献:
    名称:
    柯林斯的心木中的新木脂素
    摘要:
    据报道,从Cleistanthus collinus的心材中分离并鉴定了五种新化合物和九种已知化合物。这些新化合物是wodeshiol 16,3,4- dihydrotaiwaninÇ 20,和三个新的苷24,25和26山荷叶素的和taiwanin E中的1 H和13这些化合物的C NMR谱也报道。
    DOI:
    10.1016/s0040-4020(01)98893-3
  • 作为产物:
    描述:
    (1S,2S,4S,5'S,6R,7S,8R,9S,12S,13R,16S)-16-[(2R,3R,4S,5R,6R)-5-methoxy-6-(methoxymethyl)-3-[(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyloxan-2-yl]oxy-4-[(2S,3R,4S,5R)-3,4,5-trimethoxyoxan-2-yl]oxyoxan-2-yl]oxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane] 生成 methyl 2,3,4-tri-O-methyl-β-D-xylopyranoside
    参考文献:
    名称:
    YU, BO-YANG;HIRAI, YASUAKI;SHOJI, JUNZO;XU, GUO-JUN, CHEM. AND PHARM. BULL., 38,(1990) N, C. 1931-1935
    摘要:
    DOI:
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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。
  • 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$$^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。
  • Helianthoside from <i>Heliaster</i> <i>helianthus</i>, an asterosaponin with a C3′-sulphated pyranose
    作者:M. Jesus Vazquez、Emilio Quinoa、Ricardo Riguera、Aurelio San Martin
    DOI:10.1139/v93-151
    日期:1993.8.1

    A new asterosaponin, named helianthoside (1), has been isolated from the butanolic extract of the starfish Heliaster helianthus and its structure established on the basis of extensive spectroscopic experiments and chemical correlations. Helianthoside is the first asterosaponin with a C3′-sulphated xylopyranose. The absolute stereochemistry at C24 was determined by the Trost–Mosher method.

    从海星Heliaster helianthus的丁醇提取物中分离出一种新的asterosaponin,命名为helianthoside(1),并通过广泛的光谱实验和化学相关性确定了其结构。Helianthoside是第一种带有C3'-硫酸化木糖苷的asterosaponin。通过Trost-Mosher方法确定了C24的绝对立体化学。
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