methyl 2,3-di-O-methyl-β-D-glucopyranoside | 10227-29-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-methyl-β-D-glucopyranoside
• 英文别名: methyl 2,3-dimethyl-β-D-glucopyranoside；methyl 2,3-di-O-methyl-glucopyranoside；methyl-(O²,O³-dimethyl-β-D-glucopyranoside)；Methyl-(O²,O³-dimethyl-β-D-glucopyranosid)；Methyl-2,3-di-O-methyl-β-D-gluco-pyranosid；Methyl-2,3-di-O-methyl-β-D-glucopyranosid；(2R,3R,4S,5R,6R)-2-(hydroxymethyl)-4,5,6-trimethoxyoxan-3-ol
• CAS: 10227-29-9
• 化学式: C₉H₁₈O₆
• 分子量: 222.238
• InChiKey: NTTFSNRBMIOKLX-SYHAXYEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 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：

  methyl 2,3-di-O-methyl-β-D-glucopyranoside 生成 甲基 2,3-二-O-甲基-alpha-D-吡喃葡萄糖苷
  参考文献：
  名称：

  REUBEN, JACQUES, CARBOHYDR. RES., 184,(1988) C. 244-246

  摘要：

  DOI：
• 作为产物：
  描述：

  甲基 2,3-二-O-甲基-alpha-D-吡喃葡萄糖苷 生成 methyl 2,3-di-O-methyl-β-D-glucopyranoside
  参考文献：
  名称：

  REUBEN, JACQUES, CARBOHYDR. RES., 184,(1988) C. 244-246

  摘要：

  DOI：

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。
• New oligomeric proanthocyanidins from Alhagi pseudalhagi
  作者：D. F. Alimova、Z. A. Kuliev、S. Z. Nishanbaev、A. D. Vdovin、N. D. Abdullaev、S. F. Aripova

  DOI：10.1007/s10600-010-9615-4

  日期：2010.7

  Two new oligomeric proanthocyanidin glucosides were isolated from the aerial part and roots of Alhagi pseudalhagi. Their structures and relative configurations were elucidated as 7-O-β-D-Glc $$ \textp}}\xrightarrow6} $$ galloyl-(+)catechin-(4α-8)-(+)-catechin-(4α-8)-(–)-epigallocatechin and 7-O-β-D-Glc $$ \textp}}\xrightarrow6} $$ galloyl-(+)-catechin-[(4α-8)-(+)-catechin]3-(4α-8)-(–)-epigallocatechin-3-O-gallate.

  从草木樨状黄芪的地上部分和根部中分离出两种新的寡聚原花青素葡萄糖苷。它们的结构和相对构型被阐明为7-O-β-D-Glc $$ \textp}}\xrightarrow6} $$ 没食子酰基-(+)-儿茶素-(4α-8)-(+)-儿茶素-(4α-8)-(–)-表儿茶素和7-O-β-D-Glc $$ \textp}}\xrightarrow6} $$ 没食子酰基-(+)-儿茶素-[(4α-8)-(+)-儿茶素]3-(4α-8)-(–)-表儿茶素-3-O-没食子酸盐。
• Cleavage of 4,6-O-Benzylidene Acetal Using Sodium Hydrogen Sulfate Monohydrate
  作者：Masahiko Hayashi、Kyosuke Michigami、Manami Terauchi

  DOI：10.1055/s-0033-1338469

  日期：——

  using sodium hydrogen sulfate monohydrate under mild conditions. The use of protecting groups is an important protocol in carbohydrate synthesis. Among protecting groups, benzylidene acetals­ are generally more stable than other acetals; therefore, strong conditions are often required for deprotection. We report the deprotection of 4,6-O-benzylidene derivatives using sodium hydrogen sulfate monohydrate

  摘要 保护基的使用是碳水化合物合成中的重要方案。在保护基中，亚苄基乙缩醛通常比其他乙缩醛更稳定。因此，脱保护通常需要严格的条件。我们报道了在温和的条件下使用一水合硫酸氢钠对4,6- O-亚苄基衍生物的脱保护。 保护基的使用是碳水化合物合成中的重要方案。在保护基中，亚苄基乙缩醛通常比其他乙缩醛更稳定。因此，脱保护通常需要严格的条件。我们报道了在温和的条件下使用一水合硫酸氢钠对4,6- O-亚苄基衍生物的脱保护。
• Utilization of Sugars in Organic Synthesis. Part XXXIV. Thio-Sugars. IV. Synthesis of Carbohydrate 1,3-Glycol (Six-Membered) Thionocarbonates and Their Attempted O-S Rearrangement.
  作者：Yoshisuke TSUDA、Shinsuke NOGUCHI、Hideki NIINO

  DOI：10.1248/cpb.49.1210

  日期：——

  Four six-membered cyclic thionocarbonates (two sec-sec and two prim-sec) were prepared and their radical-promoted O-S rearrangement reaction was examined. The results revealed that the reaction in six-membered rings is difficult compared with the simple rearrangement in five-membered rings. In the course of syntheses of the substrates, interesting acyl migration during the stannylation process occurred

  制备了四个六元环状硫代碳酸酯（2秒-秒和两个伯-秒），并检查了其自由基促进的OS重排反应。结果表明，与五元环中的简单重排相比，六元环中的反应困难。在底物的合成过程中，在锡烷基化过程中发生了有趣的酰基迁移。
• Differential Reactivity of α- and β-Anomers of Glycosyl Acceptors in Glycosylations. A Remote Consequence of the <i>e</i><i>ndo</i>-Anomeric Effect?
  作者：Didier Magaud、René Dolmazon、Daniel Anker、Alain Doutheau、Yves L. Dory、Pierre Deslongchamps

  DOI：10.1021/ol006039q

  日期：2000.7.1

  onic acid esters were coupled with a 1/1 mixture of alpha and beta 2,3 di-O-protected D-galactopyranosiduronic acid esters, the beta-anomer proved to be more reactive. Data from theoretical calculations suggested that the enhanced reactivity of this anomer compared with the alpha one would be due to a stronger hydrogen bond of the C-4 OH with the ring oxygen.

  当将苯基三-O-苄基-1-硫代-β-D-吡喃半乳糖醛酸酯化合物与1/1的α和β2,3二-O-保护的D-吡喃半乳糖醛酸酯化合物混合时，证明了β-端基异构体更具反应性。来自理论计算的数据表明，与α-1相比，该端基异构体的反应性增强是由于C-4 OH与环氧的氢键更强。