O³,O⁴,O⁶-trimethyl-D-glucose | 13554-85-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O³,O⁴,O⁶-trimethyl-D-glucose
• 英文别名: (3R,4R,5R,6R)-4,5-dimethoxy-6-(methoxymethyl)oxane-2,3-diol
• CAS: 13554-85-3；14184-50-0；35775-27-0；35775-28-1；38184-02-0；52194-59-9；52194-60-2
• 化学式: C₉H₁₈O₆
• 分子量: 222.238
• InChiKey: VUWWFVHGDQPFMX-VARJHODCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 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：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  O³,O⁴,O⁶-trimethyl-D-glucose 、 六乙基亚磷酸胺 反应 1.0h， 生成 3,4,6-tri-O-methyl-β-D-glucopyranose 1,2-cyclo(diethylphosphoramidite) 、 3,4,6-tri-O-methyl-β-D-glucopyranose 1,2-cyclo(diethylphosphoramidite) 、 3,4,6-tri-O-methyl-α-D-glucopyranose 1,2-cyclo(diethylphosphoramidite) 、 3,4,6-tri-O-methyl-α-D-glucopyranose 1,2-cyclo(diethylphosphoramidite)
  参考文献：
  名称：

  Nifant'ev, E. E.; Rumyantsev, S. A.; Sisneros, Ks., Journal of general chemistry of the USSR, 1983, vol. 53, # 11, p. 2362 - 2374

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4,6-tri-O-methyl-1,2-O-ethylidene-α-D-glucopyranose 在 溶剂黄146 作用下， 反应 10.0h， 以76%的产率得到O³,O⁴,O⁶-trimethyl-D-glucose
  参考文献：
  名称：

  Nifant'ev, E. E.; Rumyantsev, S. A.; Sisneros, Ks., Journal of general chemistry of the USSR, 1983, vol. 53, # 11, p. 2362 - 2374

  摘要：

  DOI：

文献信息

• HYDROXY FATTY ACID GLYCOSIDES OF SOPHOROSE FROM TORULOPSIS MAGNOLIAE
  作者：P. A. J. Gorin、J. F. T. Spencer、A. P. Tulloch

  DOI：10.1139/v61-104

  日期：1961.4.1

  The oil formed during fermentation by a strain of Torulopsismagnoliae consisted mainly of partly acetylated 2-O-β-D-glucopyranosyl-D-glucopyranose units attached β-glycosidically to 17-L-hydroxyoctadecanoic and 17-L-hydroxy-9-octadecenoic acids.

  在Torulopsis magnoliae菌株发酵过程中形成的油主要由部分乙酰化的2-O-β-D-葡萄糖吡喃基-D-葡萄糖吡喃糖单元组成，以β-糖苷键连接到17-L-羟基十八烷酸和17-L-羟基-9-十八烯酸上。
• An isoflavone diglycoside from the seeds of Dolichos biflorus
  作者：J. Mitra、A. Das、T. Joshi

  DOI：10.1016/0031-9422(83)85069-9

  日期：1983.1

  Abstract -5-Hydroxy-7,3′,4′-trimethoxy-8-methylisoflavone 5-neohesperidoside has been identified from the seeds of Dolichos biflorus.

  摘要 -5-羟基-7,3',4'-三甲氧基-8-甲基异黄酮5-新橙皮苷已从双花桃种子中鉴定出来。
• Saponins of juk-siho and roots of Bupleurum longeradiatum Turcz.
  作者：HIROKO KIMATA、RYOJI KASAI、OSAMU TANAKA

  DOI：10.1248/cpb.30.4373

  日期：——

  In connection with our studies on the chemical evaluation of commercial Bupleuri Radix, isolation and identification of saponins of Juk-Siho (a Korean Bupleuri Radix) and roots of Bupleurum longeradiatum, the source plant of this crude drug, were carried out. From Juk-Siho, five saponins 1-5 were isolated. The saponins 1-3 were identified as saikosaponins-a (1), -c (2) and -d (3), respectively, all of which have already been isolated from roots of Bupleurum falcatum. The structures of the new saponins, named chikusaikosides-I (4) and -II (5), were estabished as 3-O-β-xylopyranosyl (1→2)-β-glucopyranosyl-(1→3)-β-fucopyranoside of saikogenin F (6) and 3-O-β-glucopyranosyl (1→6)-(α-rhamnopyranosyl (1→4)-β-glucopyranoside of 6, respectively. From roots of B. longeradiatum, saponins 1-4 were isolated and identified. During the course of the structure study of 4 by 13C-nuclear magnetic resonance (13C-NMR), an anomalous glycosylation shift for the 1, 2-linked glycoside was encountered.

  结合我们对商用柴胡的化学评估研究，我们对 Juk-Siho（一种韩国柴胡）和柴胡根（这种粗制药物的来源植物）的皂苷进行了分离和鉴定。从 Juk-Siho 中分离出五种皂苷 1-5。经鉴定，这些皂苷 1-3 分别为 saikosaponins-a (1)、-c (2) 和 -d (3)，所有这些皂苷都已从 Bupleurum falcatum 的根中分离出来。新皂甙的结构被确定为 3-O-β-xylopyranosyl-(1→2)-β-glucopyranosyl-(1→3)-β-fucopyranoside of saikogenin F (6) 和 3-O-β-glucopyranosyl (1→6)-(α-rhamnopyranosyl (1→4)-β-glucopyranoside of 6。从 B. longeradiatum 的根中分离并鉴定出了皂苷 1-4。在通过 13C 核磁共振（13C-NMR）对 4 的结构进行研究的过程中，发现 1，2-连接苷的糖基化转变异常。
• Two flavonoid glycosides from the bark of Prosopis juliflora
  作者：Ranjana Vajpeyi Nee' Shukla、Krishna Misra

  DOI：10.1016/0031-9422(81)85122-9

  日期：1981.1

  Abstract Two new glycosides, kaempferol 4′-methyl ether 3- O -β- d -galactopyranoside and retusin 7- O -neohesperidoside, have been characterized from the stem bark of Prosopis juliflora .

  摘要 山柰酚4′-甲基醚3-O-β-d-吡喃半乳糖苷和维甲素7-O-新橙皮苷两种新苷已从七叶树的茎皮中得到表征。
• New triterpenoid glycosides from the leaves of Bupleurum rotundifolium L.
  作者：YOSHIMASA KOBAYASHI、TADAHIRO TAKEDA、YUKIO OGIHARA

  DOI：10.1248/cpb.29.2222

  日期：——

  Two new triglycosides of oleanane-type triterpenes, rotundioside E (3) and F (1), isolated from the leaves of Bupleurum rotundifolium L. were identified as 16α, 28-dihydroxyoleana-11, 13 (18)-dien-3β-yl α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-fucopyranoside (3) and 13β, 28-epoxy-16α-hydroxyoleana-11-en-3β-yl α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-fucopyranoside (1), respectively, on the basis of chemical and spectroscopic evidence.

  从Bupleurum rotundifolium L.叶片中分离出的两种新的齐墩果烷型三萜类化合物--罗汉果苷E (3)和F (1)，被鉴定为16α, 28-二羟基油菜-11, 13 (18)-dien-3β-yl α-L→2）-β-吡喃葡萄糖基被鉴定为 16α，28-二羟基油菜-11，13 (18)-二烯-3β-基 α-L-鼠李糖基-(1→2)-β-D-吡喃葡萄糖基-(1→2)-β-D-吡喃葡萄糖苷 (3) 和 13β、28-epoxy-16α-hydroxyoleana-11-en-3β-yl α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-fucopyranoside (1)。