methyl 3,4,6-tri-O-benzyl-2-deoxy-αβ-D-gluco-pyranoside | 184653-30-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4,6-tri-O-benzyl-2-deoxy-αβ-D-gluco-pyranoside
• 英文别名: methyl 2-deoxy-3,4,6-tri-O-benzyl-α/β-D-gluco-/mannopyranoside；(2R,3S,4R)-6-methoxy-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxane
• CAS: 184653-30-3
• 化学式: C₂₈H₃₂O₅
• 分子量: 448.559
• InChiKey: QGZHSZVCTPWCDC-YBOHRUJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3,4,6-tri-O-benzyl-2-deoxy-αβ-D-gluco-pyranoside 在 磺酰胺 作用下， 以 乙腈 为溶剂， 反应 0.08h， 以94%的产率得到(2R,3S,4R,6R)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-(sulfamoylamino)oxane
  参考文献：
  名称：

  Sulfonamidoglycosylation of Methyl Glycosides Employing Perchloric Acid Supported on Silica Gel

  摘要：

  The sulfonamidoglycosylation of methyl glycosides in the presence of perchloric acid immobilized on silica gel proceeded effectively to afford the corresponding sulfonamido glycosides with good to high yields with minimal workup and short reaction times. This methodology was applied to the synthesis of some N-glycosyl sulfamides, which showed low nanomolar activity against human carbonic anhydrase.

  DOI：

  10.1080/07328300802030829
• 作为产物：
  描述：

  chloro-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranoside 在 甲醇 、 calcium sulfate 、 氢氧化钾 、 2-甲基十一烷-2-硫醇 、 六氯乙烷 、 碘 、 碳酸氢钠 、 silver sulfate 、 N,N-二异丙基乙胺 、 naphthalen-1-yl-lithium 、 间氯过氧苯甲酸 、 N,N'-二环己基碳二亚胺 、 lithium diisopropyl amide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 13.17h， 生成 methyl 3,4,6-tri-O-benzyl-2-deoxy-αβ-D-gluco-pyranoside
  参考文献：
  名称：

  Crich, David; Ritchie, Timothy J., Journal of the Chemical Society. Perkin transactions I, 1990, # 4, p. 945 - 954

  摘要：

  DOI：

文献信息

• [EN] PROCESS FOR THE SYNTHESIS OF 2-DEOXY-D-GLUCOSE<br/>[FR] PROCESSUS DE SYNTHESE DE DEOXY-D-GLUCOSE
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2004058786A1

  公开（公告）日：2004-07-15

  The present invention provides a process for the synthesis of 2-deoxy-D-glucose comprising haloalkoxylation of R-D-Glucal wherein R is selected from H and 3, 4, 6-tri-O-benzyl, to obtain alkyl 2-deoxy-2-halo-R-α/β-D-gluco/mannopyranoside, converting alkyl 2-deoxy-2-halo-R-α/$(b)-D-gluco/mannopyranoside by reduction to alkyl 2-deoxy-α/$(b)-D-glucopyranoside, hydrolysing alkyl 2-deoxy-α/$(b)-D-glucopyranoside to 2-deoxy-D-glucose.

  该发明提供了一种合成2-脱氧-D-葡萄糖的过程，包括对R-D-葡糖进行卤代烯氧基化，其中R选择自H和3,4,6-三-O-苄基，以获得烷基2-脱氧-2-卤代-R-α/β-D-葡萄/甘露聚糖苷，将烷基2-脱氧-2-卤代-R-α/β-D-葡萄/甘露聚糖苷通过还原转化为烷基2-脱氧-α/β-D-葡萄糖吡喃苷，将烷基2-脱氧-α/β-D-葡萄糖吡喃苷水解为2-脱氧-D-葡萄糖。
• Bisglycosyl Peroxides
  作者：Marek Chmielewski、Wioletta Kośnik、Barbara Grzeszczyk

  DOI：10.1055/s-2007-991090

  日期：——

  Tri-O-benzyl-d-glycal treated with per-O-benzyl-2-deoxy-α- or per-O-benzyl-2-deoxy-β-d-glycosyl hydroperoxide affords the corresponding bisglycosyl peroxides. In all cases a new α-glycosidic bond is formed. Formation of the peroxide is not a reversible process; under applied reaction conditions, we did not observe rearrangement of β,α-peroxide into the corresponding α,α-compounds.

  三O-苄基-d-甘露糖在per-O-苄基-2-脱氧-α-或per-O-苄基-2-脱氧-β-d-糖苷过氧化物的处理下，生成相应的双糖苷过氧化物。在所有情况下，形成了新的α-糖苷键。过氧化物的形成不是一个可逆的过程；在所施加的反应条件下，我们没有观察到β,α-过氧化物转变为相应的α,α-化合物。
• Aluminium triflate catalysed O-glycosidation: temperature-switched selective Ferrier rearrangement or direct addition with alcohols
  作者：D. Bradley G. Williams、Sandile B. Simelane、Henok H. Kinfe

  DOI：10.1039/c2ob25540e

  日期：——

  A temperature-controlled mechanism switch between the Al(OTf)3-catalysed direct addition of alcohols or the Ferrier rearrangement reactions in some glycals is presented. The scope and limitations are investigated as are the influence of the stereochemistry and nature of the protecting groups on the glycal substrate.

  提出了在Al（OTf）3催化的醇直接添加或某些糖基中的Ferrier重排反应之间的温度控制机制切换。研究了范围和局限性以及糖基上保护基的立体化学和性质的影响。
• Process for the synthesis of 2-deoxy-D-glucose
  申请人：——

  公开号：US20040185538A1

  公开（公告）日：2004-09-23

  The present invention provides a process for the synthesis of 2-deoxy-D-glucose comprising haloalkoxylation of R-D-Glucal wherein R is selected from H and 3, 4, 6-tri-O-benzyl, to obtain alkyl 2-deoxy-2-halo-R-&agr;/&bgr;-D-gluco/mannopyranoside, converting alkyl 2-deoxy-2-halo-R-&agr;/&bgr;-D-gluco/mannopyranoside by reduction to alkyl 2-deoxy-&agr;/&bgr;-D-glucopyranoside, hydrolysing alkyl 2-deoxy-&agr;/&bgr;-D-glucopyranoside to 2-deoxy-D-glucose.

  本发明提供了一种合成2-脱氧-D-葡萄糖的方法，包括对R-D-葡萄糖醛进行卤代烷氧化反应，其中R选择自H和3,4,6-三-O-苄基，以获得烷基2-脱氧-2-卤代-R-α/β-D-葡萄/甘露聚糖苷，将烷基2-脱氧-2-卤代-R-α/β-D-葡萄/甘露聚糖苷通过还原转化为烷基2-脱氧-α/β-D-葡萄糖苷，将烷基2-脱氧-α/β-D-葡萄糖苷水解为2-脱氧-D-葡萄糖。
• Ceric Ammonium Nitrate-Catalyzed Tetrahydropyranylation of Alcohols and Synthesis of 2-Deoxy-O-Glycosides
  作者：Kandasamy Pachamuthu、Yashwant D. Vankar

  DOI：10.1021/jo0103322

  日期：2001.11.1