methyl 2,3,4-tri-O-benzyl-α-D-xylopyranoside | 20787-14-8

• 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-benzyl-α-D-xylopyranoside
• 英文别名: (2S,3R,4S,5R)-2-methoxy-3,4,5-tris(phenylmethoxy)oxane
• CAS: 20787-14-8
• 化学式: C₂₇H₃₀O₅
• 分子量: 434.532
• InChiKey: CVWJHEJDZRHTCM-RAVGUYNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  32.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzyl-α-D-xylopyranoside 在 咪唑 、 硫酸 、 碳酸氢钠 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 52.58h， 生成 (2R,3S,4R,5R)-5-[(N-benzyl-N-(benzyloxycarbonyl))amino]-2,3,4-tris(benzyloxy)-hept-6-en-1-ol
  参考文献：
  名称：

  由甲基α-d-吡喃吡喃糖苷合成正烷烷生物碱calystine B2。

  摘要：

  描述了形成中央环庚酮中间体的新合成途径，该中间体导致降冰片烷生物碱calystegine B2。该方法直接在闭环复分解步骤中安装所需的酮官能团。由市售的甲基α-d-吡喃吡喃糖苷经10个步骤制备目标化合物。

  DOI：

  10.1016/j.carres.2018.12.002
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-β-D-xylopyranoside 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 2,3,4-tri-O-benzyl-α-D-xylopyranoside
  参考文献：
  名称：

  四氯化钛快速异构化聚-O-苄基-β-D-吡喃葡萄糖苷的研究

  摘要：

  四氯化钛在 25 °C 的二氯甲烷中快速异构化甲基 2,3,4,6-四-O-苄基-β-D-吡喃葡萄糖苷。描述了 C-5 上的苄氧基甲基和糖苷的环氧协同促进反应的证据。该试剂将几种二糖衍生物的糖苷间键异构化。

  DOI：

  10.1246/bcsj.55.1092

文献信息

• Mild Deprotection of Benzyl Ether Protective Groups with Ozone
  作者：Pierre Angibeaud、Jacques Defaye、Andrée Gadelle、Jean-Pierre Utille

  DOI：10.1055/s-1985-31447

  日期：——

  Benzyl ether protective groups are oxidatively removed by ozone under relatively mild conditions. Reaction products are benzoic ester, benzoic acid, and the corresponding alcohol. Subsequent deacylation with sodium methoxide affords a convenient debenzylation technique which has been applied to various O-benzyl protected carbohydrates 1 to afford the deprotected species 2. Glycosides and acetals are unaffected by the treatment.

  苄醚保护基在相对温和的条件下可通过臭氧进行氧化性去除。反应产物为苯甲酸酯、苯甲酸和相应的醇。随后用甲醇钠进行脱酰反应，提供了一种便捷的去苄基化技术，该技术已应用于各种O-苄基保护的碳水化合物1，得到去保护的物种2。糖苷和缩醛不受此处理影响。
• The Direct Synthesis of Methyl 2,4-Di-<i>O</i>-benzyl-α-D-xylopyranoside by the Regiospecific Benzylation of Methyl α-D-Xylopyranoside
  作者：Naohiko Morishima、Shinkiti Koto、Chiharu Kusuhara、Shonosuke Zen

  DOI：10.1246/bcsj.55.631

  日期：1982.2

  The regiospecific benzylation of methyl α-D-xylopyranoside with benzyl chloride and sodium hydride produces methyl 2,4-di-O-benzyl-α-D-xylopyranoside in a 70% yield, together with the by-products, methyl 2,3- and 3,4-di-O-benzyl-α-D-xylopyranosides. The structure of the 2,4-di-O-benzyl derivative was confirmed through the alternative synthesis of the 2,3- and 3,4-di-O-benzyl derivatives via the O-isopropylidene

  甲基 α-D-吡喃木糖苷与苄基氯和氢化钠的区域特异性苄基化以 70% 的产率产生甲基 2,4-二-O-苄基-α-D-吡喃木糖苷，以及副产物甲基 2,3 - 和 3,4-二-O-苄基-α-D-吡喃木糖苷。通过甲基α的O-异亚丙基和O-环己叉衍生物交替合成2,3-和3,4-二-O-苄基衍生物，证实了2,4-二-O-苄基衍生物的结构-D-吡喃木糖苷。
• Novel <scp>d</scp>-Xylose Derivatives Stimulate Muscle Glucose Uptake by Activating AMP-Activated Protein Kinase α
  作者：Arie Gruzman、Ofer Shamni、Moriya Ben Yakir、Daphna Sandovski、Anna Elgart、Evgenia Alpert、Guy Cohen、Amnon Hoffman、Yehoshua Katzhendler、Erol Cerasi、Shlomo Sasson

  DOI：10.1021/jm8008713

  日期：2008.12.25

  Type 2 diabetes mellitus has reached epidemic proportions; therefore, the search for novel antihyperglycemic drugs is intense. We have discovered that D-Xylose increases the rate of glucose transport in a non-insulin-dependent manner in rat and human myotubes in vitro. Due to the unfavorable pharmacokinetic properties Of D-Xylose we aimed at synthesizing active derivatives with improved parameters. Quantitative structure-activity relationship analysis identified critical hydroxyl groups in D-xylose. These data were used to synthesize various hydrophobic derivatives Of D-Xylose of which compound 19 the was most potent compound in stimulating the rate of hexose transport by increasing the abundance of glucose transporter-4 in the plasma membrane of myotubes. This effect resulted from the activation of AMP-activated protein kinase without recruiting the insulin transduction mechanism. These results show that lipophilic D-Xylose derivatives may serve as prototype molecules for the development of novel anti hyperglycemic drugs for the treatment of diabetes.
• Analysis of UDP-<scp>d</scp>-Apiose/UDP-<scp>d</scp>-Xylose Synthase-Catalyzed Conversion of UDP-<scp>d</scp>-Apiose Phosphonate to UDP-<scp>d</scp>-Xylose Phosphonate: Implications for a Retroaldol–Aldol Mechanism
  作者：Sei-hyun Choi、Steven O. Mansoorabadi、Yung-nan Liu、Tun-Cheng Chien、Hung-wen Liu

  DOI：10.1021/ja305322x

  日期：2012.8.29

  UDP-D-apiose/UDP-D-xylose synthase (AXS) catalyzes the conversion of UDP-D-glucuronic acid to UDP-D-apiose and UDP-D-xylose. An acetyl-protected phosphonate analogue of UDP-D-apiose was synthesized and used in an in situ HPLC assay to demonstrate for the first time the ability of AXS to interconvert the two reaction products. Density functional theory calculations provided insight into the energetics of this process and the apparent inability of AXS to catalyze the conversion of UDP-D-xylose to UDP-D-apiose. The data suggest that this observation is unlikely to be due to an unfavorable equilibrium but rather results from substrate inhibition by the most stable chair conformation of UDP-D-xylose. The detection of xylose cyclic phosphonate as the turnover product reveals significant new details about the AXS-catalyzed reaction and supports the proposed retroaldol-aldol mechanism of catalysis.
• NIFANIEV, NIKOLAY E.;BACKINOWSKY, LEON V.;KOCHETKOV, NIKOLAY K., CARBOHYDR. RES., 191,(1989) N, C. 13-19
  作者：NIFANIEV, NIKOLAY E.、BACKINOWSKY, LEON V.、KOCHETKOV, NIKOLAY K.

  DOI：——

  日期：——