methyl 3,4-di-O-benzyl-2-deoxy-D-arabino-hexopyraboside | 675128-77-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4-di-O-benzyl-2-deoxy-D-arabino-hexopyraboside
• 英文别名: [(2R,3S,4R)-6-methoxy-3,4-bis(phenylmethoxy)oxan-2-yl]methanol
• CAS: 675128-77-5
• 化学式: C₂₁H₂₆O₅
• 分子量: 358.434
• InChiKey: CABYEFIDFUEUJV-OKDUWWRPSA-N

物化性质

• 沸点：
  492.3±45.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3,4-di-O-benzyl-2-deoxy-D-arabino-hexopyraboside 在 咪唑 、 碘 、 mercury(II) trifluoroacetate 、 sodium hydride 、 甲基磺酰氯 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 0.5h， 生成 GS 416
  参考文献：
  名称：

  Synthetic studies on antascomicin A: construction of the C18–C34 fragment

  摘要：

  Stereoselective synthesis of the C18-C34 fragment of antascomicin A is described. Construction of the C27-C34 carbocycle moiety was achieved via catalytic Ferrier carbocylization and Johnson-Claisen rearrangement, which was converted to iodide 2 by use of asymmetric alkylation and Sharpless epoxidation as key transformations. Coupling of iodide 2 and sulfone 3 furnished the C18-C34 fragment. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.04.072
• 作为产物：
  描述：

  2-Deoxy-D-glucose 在 aluminum (III) chloride 、 borane-trimethylamine 、 sodium hydride 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 72.0h， 生成 methyl 3,4-di-O-benzyl-2-deoxy-D-arabino-hexopyraboside
  参考文献：
  名称：

  Chiral pool synthesis of calystegine A3 from 2-deoxyglucose via a Brown allylation

  摘要：

  Calystegine A(3) is a naturally occurring nortropane iminosugar of which there previously have been three total syntheses. Inspired by our previous work we here report on a fourth approach using 17 steps from 2-deoxy-D-glucose applying a diastereoselective allylation protocol. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.10.025

文献信息

• Substituent effects on the SmI2/Pd(0)-promoted carbohydrate ring-contraction of 5-alkynylpyranosides
  作者：José M. Aurrecoechea、Jesús H. Gil、Beatriz López

  DOI：10.1016/s0040-4020(03)01103-7

  日期：2003.9

  The effect of substituents on the reactivity and stereoselectivity of the SmI2/Pd(0)-promoted ring-contraction of 5-alkynylpyranosides has been examined using substrates substituted only at selected positions. While formation of 2-ethynylcyclopentanols takes place efficiently, an internal alkyne did not afford the expected product. The presence of peripheral alkoxy substituents leads to variable stereoselectivities that depend on the number and orientation of such groups. Thus, an isolated OBn substituent at C(3) (carbohydrate numbering) exerts a significant stereochemical control while additional substitution with the same group at C(4) either enhances or drastically reduces stereoselectivity depending on its orientation (alpha or beta, respectively). (C) 2003 Elsevier Ltd. All rights reserved.
• Chiral pool synthesis of calystegine A3 from 2-deoxyglucose via a Brown allylation
  作者：Tina Secher Rasmussen、Henrik Helligsø Jensen

  DOI：10.1016/j.carres.2011.10.025

  日期：2011.12

  Calystegine A(3) is a naturally occurring nortropane iminosugar of which there previously have been three total syntheses. Inspired by our previous work we here report on a fourth approach using 17 steps from 2-deoxy-D-glucose applying a diastereoselective allylation protocol. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthetic studies on antascomicin A: construction of the C18–C34 fragment
  作者：Haruhiko Fuwa、Yumiko Okamura、Hideaki Natsugari

  DOI：10.1016/j.tet.2004.04.072

  日期：2004.6

  Stereoselective synthesis of the C18-C34 fragment of antascomicin A is described. Construction of the C27-C34 carbocycle moiety was achieved via catalytic Ferrier carbocylization and Johnson-Claisen rearrangement, which was converted to iodide 2 by use of asymmetric alkylation and Sharpless epoxidation as key transformations. Coupling of iodide 2 and sulfone 3 furnished the C18-C34 fragment. (C) 2004 Elsevier Ltd. All rights reserved.