methyl 3,4,6-tri-O-benzyl-2-deoxy-D-galactopyranoside | 230974-54-6

• 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-D-galactopyranoside
• 英文别名: (2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran；(2R,3R,4R)-6-methoxy-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxane
• CAS: 230974-54-6
• 化学式: C₂₈H₃₂O₅
• 分子量: 448.559
• InChiKey: QGZHSZVCTPWCDC-XSKUQLBKSA-N

物化性质

• 沸点：
  564.6±50.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

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-D-galactopyranoside 在 磺酰胺 作用下， 以 乙腈 为溶剂， 反应 0.08h， 以95%的产率得到(2R,3R,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：

  甲醇 、 3,4,6-三邻苄基半乳醛 在 ammonium cerium(IV) nitrate 作用下， 以 乙腈 为溶剂， 以78%的产率得到methyl 3,4,6-tri-O-benzyl-2-deoxy-D-galactopyranoside
  参考文献：
  名称：

  Ceric Ammonium Nitrate-Catalyzed Tetrahydropyranylation of Alcohols and Synthesis of 2-Deoxy-O-Glycosides

  摘要：

  DOI：

  10.1021/jo0103322

文献信息

• Enantioselective Epoxidation of Electrophilic Olefins by Using Glycosyl Hydroperoxides
  作者：Wioletta Kośnik、Wojciech Bocian、Lech Kozerski、Igor Tvaroška、Marek Chmielewski

  DOI：10.1002/chem.200800051

  日期：2008.7.7

  Anomeric hydroperoxides derived from 3,4,6-tri-O-benzyl-galactose and glucose were used for enantioselective epoxidation of naphthoquinone (12), chalcone (13), (E)-1,2-dibenzoyl ethylene (14) and (E)-iso-butyryl-phenyl ethylene (15). In the presence of sodium hydroxide, the epoxidations showed exceptional high asymmetric induction. The exchange of sodium by a potassium ion resulted in a low asymmetric

  衍生自3,4,6-三-O-苄基-半乳糖和葡萄糖的端基氢过氧化物用于萘醌（12），查尔酮（13），（E）-1,2-二苯甲酰基乙烯（14）和（ E）-异丁酰基-苯基乙烯（15）。在氢氧化钠存在下，环氧化显示出异常的高不对称诱导。通过钾离子交换钠导致低的不对称诱导。这些结果指出了抗衡离子的关键作用，并强烈建议在环氧化过程的过渡态中，氢过氧化物和烯烃这两种试剂均会发生碱性离子的配位。DFT B3LYP / 6-31G *水平上反应机理的理论研究与实验结果非常吻合。
• 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。
• Diastereoselective synthesis of β-(3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-N-tert-butoxycarbonyl-D-alanine
  作者：Albrecht Lieberknecht、Helmut Griesser、Bernd Krämer、Rodolfo D. Bravo、Pedro A. Colinas、Raúl J. Grigera

  DOI：10.1016/s0040-4020(99)00306-3

  日期：1999.5

  Key steps in the synthesis of beta-(3,4,6-tri-O-benzyl-2-deoxy-beta-D-galactopyranosyl)-N-tert-butoxycarbonyl-D-alanine are the Wittig reaction of 2-deoxy-galactopyranosylphosphonium salt 2 and Garner aldehyde, as well as the subsequent diastereoselective hydrogenation of the olefinated sugar 3a,b. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Sulfonamidoglycosylation of methyl ribofuranosides: a novel approach to furanosylsulfonamides
  作者：Pedro A. Colinas、Rodolfo D. Bravo

  DOI：10.1016/j.tetlet.2005.01.065

  日期：2005.3

  The sulfonarnidoglycosylation of benzylated methyl ribofuranosides using boron trifluoride etherate as catalyst, proceeded effectively to give the new sulfonamidofuranosides with good to high yields. (C) 2005 Elsevier Ltd. All rights reserved.
• Stereoselective <i>gem</i>-C,B-Glycosylation via 1,2-Boronate Migration
  作者：Wei-Cheng Zhao、Rui-Peng Li、Chao Ma、Qi-Ying Liao、Miao Wang、Zhi-Tao He

  DOI：10.1021/jacs.1c11842

  日期：2022.2.16