methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside | 29600-81-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside
• 英文别名: methyl 2,3-di-O-benzyl-4,6-benzylidene-α-D-galactopyranoside；methyl 2,3-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside；Methyl 2,3-DI-O-benzyl-4,6-O-benzylidene-A-D-galactopyranoside；(4aR,6S,7R,8S,8aS)-6-methoxy-2-phenyl-7,8-bis(phenylmethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 29600-81-5
• 化学式: C₂₈H₃₀O₆
• 分子量: 462.543
• InChiKey: CVHUOBYFXKHVJR-BBNIJSTKSA-N

物化性质

• 沸点：
  585.4±50.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranoside 在 吡啶 、 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 methyl 2,3,6-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  pseudo假二糖

  摘要：

  描述了几种基于氨基吡喃葡萄糖的am假二糖的合成。由于与糖酵解中涉及的还原和非还原吡喃糖单元的结构相似，它们可以用作糖苷酶抑制剂。

  DOI：

  10.1016/0040-4039(93)88054-m
• 作为产物：
  描述：

  methyl 4,6-O-benzylidene-α-D-galactopyranoside 以100%的产率得到
  参考文献：
  名称：

  BERNOTAS, RONALD C., TETRAHEDRON LETT., 31,(1990) N, C. 469-472

  摘要：

  DOI：

文献信息

• Cleavage of 2-Phenyl-1,3-dioxolanes and Benzyl Ethers by Catalytic Transfer Hydrogenation
  作者：Tadeusz Bieg、Wiesław Szeja

  DOI：10.1055/s-1986-31597

  日期：——

  The selective deprotection of 2-phenyl-1,3-dioxolane derivatives and benzyl ethers of carbohydrates can be accomplished by catalytic transfer hydrogenation using hydrazine hydrate as hydrogen donor and 10% palladium on carbon as catalyst. Under these conditions, 2-phenyl-1,3-dioxan and 2-alkyl-substituted 1,3-dioxolane moieties remain unaffected. The proposed method is effective and the deprotected compounds are obtained in high yields.

  通过使用水合肼作为氢供体和10%钯碳作为催化剂的催化转移氢化反应，可以选择性地脱除2-苯基-1,3-二氧戊环衍生物和碳水化合物苄醚的保护基。在这些条件下，2-苯基-1,3-二氧杂环以及2-烷基取代的1,3-二氧戊环部分保持不受影响。该方法有效且脱保护产物以高产率获得。
• Synthesis of methyl derivatives of uronic acids. I. Synthesis of methyl (methylα-D-galactopyranosid)uronate and its 2-, 3-, and 4-O-methyl ethers
  作者：V. I. Grishkovets、A. E. Zemlyakov、V. Ya. Chirva

  DOI：10.1007/bf00580445

  日期：1982.5

  Alternative unidirectional methods for synthesizing methyl (methyl α-D-galactopyranosid)uronate and its mono-O-methyl ethers by the oxidation (with CrO3-H2SO4-acetone) of the corresponding methyl O-benzyl-O-methyl-α-D-galactopyranosides having unsubstituted 6-OH groups to the corresponding methyl O-benzyl-O-methyl-α-D-galactouronic acids followed by esterification with CH2N2 and the catalytic hydrogenolysis

  通过相应的甲基 O-苄基-O-甲基-α-D-氧化（用 CrO3-H2SO4-丙酮）合成（甲基 α-D-吡喃半乳糖苷）糖醛酸甲酯及其单-O-甲基醚的替代单向方法提出了具有未取代的 6-OH 基团的吡喃半乳糖苷与相应的甲基 O-苄基-O-甲基-α-D-半乳糖醛酸，然后用 CH2N2 酯化和苄基的催化氢解。
• A short, versatile approach to polyhydroxylated pyrrolidines utilizing a reductive elimination-reductive amination as a key step
  作者：Ronald C Bernotas

  DOI：10.1016/0040-4039(90)87010-w

  日期：1990.1

  An efficient synthesis of epimeric alpha-vinyl pyrrolidines starting from methyl 4,6--benzylidene gluco- and galactopyranosides gave ready access to hydroxylated pyrrolidines.

  由甲基4，6-亚苄基葡萄糖和吡喃半乳糖苷开始的高效异构体α-乙烯基吡咯烷酮的合成容易获得羟基化的吡咯烷酮。
• Solvent-free benzylation of polyols by phase-transfer catalysis or supported reagent methods
  作者：Didier Dubreuil、Jeannine Cleophax、André Loupy

  DOI：10.1016/0008-6215(94)90012-4

  日期：1994.1

  Abstract Solvent-free techniques were successfully and efficiently applied under mild conditions to the perbenzylation of methyl α- d -glucopyranoside and methyl 6-bromo(and 6-chloro)-6-deoxy-α- d -glucopyranoside, and to the selective monobenzylation of diethyl (R,R)-tartrate. Selective 2-O- or 3-O-benzylation of methyl 4,6-O-benzylidene-α- d -galactopyranoside, requiring CH2Cl2 as solvent, was observed

  摘要在温和条件下成功，有效地将无溶剂技术应用于甲基α-d-吡喃葡萄糖苷和甲基6-溴（和6-氯）-6-脱氧-α-d-吡喃葡萄糖苷的过苄基化反应以及选择性的单苄基化反应（R，R）-酒石酸二乙酯 根据铵催化剂的性质，观察到需要CH 2 Cl 2作为溶剂的甲基4，6-O-亚苄基-α-d-吡喃半乳糖苷的选择性2-O-或3-O-苄基化。
• Synthesis of Monomethyl Derivatives of<i>P</i>-Nitrophenyl α-D-Gluco, Galacto, and Mannopyranosides and their Hydrolytic Properties Against α-Glycosidases
  作者：Wataru Hakamata、Toshiyuki Nishio、Reiko Sato、Takahiro Mochizuki、Kazuya Tsuchiya、Maki Yasuda、Tadatake Oku

  DOI：10.1080/07328300008544084

  日期：2000.1

  All possible monomethyl derivatives of p-nitrophenyl alpha-D-gluco, galacto, and mannopyranosides were synthesized. Hydrolytic activities of alpha-glucosidase (rice), alpha-galactosidases (green coffee bean, Mortierella vinacea, and Aspergillus niger), and alpha-mannosidases (almond and jack bean) against them were elucidated. The 6-O-methyl galactopyranoside and mannopyranoside were hydrolyzed by the M. vinacea alpha-galactosidase and the almond and jack bean alpha-mannosidases, respectively, while these enzymes did not act on the 2-, 3-, and 4-O-methyl derivatives. On the other hand, lice alpha-glucosidase and green coffee bean and A. niger alpha-galactosidases had no hydrolyzing activities at all against the respective four monomethylated substrates.