2,3,4-tri-O-methyl-D-xylose | 1130-67-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-methyl-D-xylose
• 英文别名: (3R,4S,5R)-3,4,5-trimethoxytetrahydro-2H-pyran-2-ol；2,3,4-tri-O-methyl-D-xylopyranoside；2,3,4-tri-O-methyl-D-xylopyranose；2,3,4-tri-O-methyl-L-xylopyranose；2,3,4-tri-O-methyl xylose；2,3,4-tri-O-methyl-xylose；2,3,4-tri-O-methylxylopyranose；(3R,4S,5R)-3,4,5-trimethoxyoxan-2-ol
• CAS: 1130-67-2；7434-17-5；14187-52-1；16742-41-9；27963-91-3；54192-87-9；60325-15-7；60687-08-3；90364-49-1
• 化学式: C₈H₁₆O₅
• 分子量: 192.212
• InChiKey: AIVDIFJVLZSYIK-MOMMNUENSA-N

物化性质

• 沸点：
  272.0±40.0 °C(predicted)
• 密度：
  1.14±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.62
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-methyl-D-xylose 在 溴 作用下， 以 水 为溶剂， 反应 10.0h， 以80 mg的产率得到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：

  [(2R,3R,4S,5R,6R)-4-[(2S,3R,4R,5S,6S)-4,5-dimethoxy-6-methyl-3-[(2S,3R,4S,5R)-3,4,5-trimethoxyoxan-2-yl]oxyoxan-2-yl]oxy-6-[2-(3,4-dimethoxyphenyl)ethoxy]-5-methoxy-2-(methoxymethyl)oxan-3-yl] (E)-3-(3,4-dimethoxyphenyl)prop-2-enoate 生成 2,3,4-tri-O-methyl-D-xylose
  参考文献：
  名称：

  CALIS, I.;BASARAN, A. A.;SARACOGLU, I.;STICHER, O.;RUEDI, P., PHYTOCHEMISTRY, 29,(1990) N, C. 1253-1257

  摘要：

  DOI：

文献信息

• Steroid saponins and sapogenins ofAllium. XVII. The structure of karatavioside C
  作者：Yu. S. Vollerner、M. B. Gorovits、T. T. Gorovits、N. K. Abubakirov

  DOI：10.1007/bf00567288

  日期：——

  A new furostanol glycoside — karatavioside C (I) has been isolated from a methanolic extract of the inflorescences ofAllium karataviense Rgl. (family Liliaceae). By the complete acid hydrolysis, enzymatic hydrolysis, methylation, and reduction of compound (I), and also by the reduction of yuccagenin (II), the structure of the glycoside (I) has been established as 25(R)-furost-5-ene-2α, 3β, 22α, 26-tetrao]

  一种新的呋喃甾醇糖苷 — karatavioside C (I) 已从 Allium karataviense Rgl 的花序的甲醇提取物中分离出来。（百合科）。通过化合物(I)的完全酸水解、酶水解、甲基化和还原，以及通过丝兰素(II)的还原，糖苷(I)的结构已确定为25(R)-furost-5 -ene-2α, 3β, 22α, 26-tetrao] 26-0-β-D-吡喃葡萄糖苷 3-0-[0-β-D-吡喃葡萄糖苷-(1→2)][0-β-D-吡喃木糖苷-(1→3)]-0-β-D-吡喃葡萄糖基-(1→4)-β-D-吡喃半乳糖苷。
• 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。
• Total Synthesis of Clavosolide A via Asymmetric Alcohol‐Mediated Carbonyl Allylation: Beyond Protecting Groups or Chiral Auxiliaries in Polyketide Construction
  作者：James M. Cabrera、Michael J. Krische

  DOI：10.1002/anie.201906259

  日期：2019.7.29

  The 20‐membered marine macrodiolide clavosolide A is prepared in 7 steps (LLS) in the absence of protecting groups or chiral auxiliaries via enantioselective alcohol‐mediated carbonyl addition. In 9 prior total syntheses, 11–34 steps (LLS) were required.

  20 元海洋大二内酯 clavosolide A 在没有保护基团或手性助剂的情况下，通过对映选择性醇介导的羰基加成，经过 7 个步骤 (LLS) 制备。在之前的 9 次全合成中，需要 11-34 个步骤 (LLS)。
• 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。
• Total Synthesis of the Marine Natural Product (−)-Clavosolide A. A Showcase for the Petasis−Ferrier Union/Rearrangement Tactic
  作者：Amos B. Smith、Vladimir Simov

  DOI：10.1021/ol0611752

  日期：2006.7.1

  see text] The total synthesis of the marine diolide (-)-clavosolide A has been achieved in 17 steps (longest linear sequence) from commercially available crotonaldehyde exploiting the Petasis-Ferrier union/rearrangement tactic to construct the requisite aglycon monomer. A one-pot esterification/lactonization employing the Yamaguchi protocol, followed by bis-glycosidation, furnished (-)-clavosolide A

  [结构：见正文]利用Petasis-Ferrier结合/重排策略构建必要的糖苷配基单体，从市售巴豆醛以17个步骤（最长的线性序列）完成了海洋乙交酯（-）-clavosolide A的总合成。使用Yamaguchi方案进行一锅酯化/内酯化，然后进行双糖苷化，提供（-）-clavosolideA。