1,2-O-isopropylidene-3-O-methyl-6-O-(p-toluenesulfonyl)-α-D-glucofuranose | 32579-95-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-O-isopropylidene-3-O-methyl-6-O-(p-toluenesulfonyl)-α-D-glucofuranose
• 英文别名: O-isopropylidene-1,2-O-methyl-3-O-p-toluenesulfonyl-6-α-D-glucofurannose；1,2-o-isopropylidene-3-O-methyl-6-O-p-toluenesulfonyl-α-D-glucofuranose；1,2-O-isopropylidene-3-O-methyl-6-p-toluenesulfonyl-α-D-glucofuranose；1,2-O-isopropylidene-3-O-methyl-6-O-tosyl-α-D-glucofuranose；[(2R)-2-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxyethyl] 4-methylbenzenesulfonate
• CAS: 32579-95-6
• 化学式: C₁₇H₂₄O₈S
• 分子量: 388.439
• InChiKey: COXQSYKZTCFSOW-IBEHDNSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-3-O-methyl-6-O-(p-toluenesulfonyl)-α-D-glucofuranose 在 镍 吡啶 、 sodium azide 、 一水合肼 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 5,6-di-amino-5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-β-L-idofuranose
  参考文献：
  名称：

  Mild and efficient synthesis of 5,6-diamino-5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-β-l-idofuranose: precursor of the first carbohydrate-derived chiral Mn(III)–salen complex

  摘要：

  Carbohydrates as multifunctional naturally occurred chiral products were used for the first time as chiral building blocks in Mn(III)-salen complexes as catalysts for the enantioselective epoxidation of alkenes. The pathways of the mild and efficient synthesis of a Mn(III)-salen complex and its diamino precursor 5,6-diamino-5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-beta-L-idofuranose starting from D-(+)-glucose are described. The complex efficiently catalyzed the epoxidation of styrene and 1,2-dihydronaphthalene, using aqueous sodium hypochlorite in CH2Cl2 as terminal oxidant. The enantiomeric excesses were 13 and 33%, respectively. Mn(III)-salen catalyst with only one stereogenic carbon atom that is adjacent to nitrogen atom proved to be able to show enantioselectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01294-2
• 作为产物：
  描述：

  5-O-carbamoyl-6-chloro-6-deoxy-1,2-O-isopropylidene-3-O-methyl-α-D-glucofuranose 在 吡啶 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 62.0h， 生成 1,2-O-isopropylidene-3-O-methyl-6-O-(p-toluenesulfonyl)-α-D-glucofuranose
  参考文献：
  名称：

  Barton, Derek H. R.; Motherwell, William B., Journal of the Chemical Society. Perkin transactions I, 1980, p. 1124 - 1131

  摘要：

  DOI：

文献信息

• Catalytic Enantioselective Reactions Part 7. Synthesis of New β-Aminoalcohols Derived from α-D-Glucose as Chiral Catalysts for the Catalytic Enantioselective Addition of Diethylzinc to Aldehydes
  作者：Byung Tae Cho、Namdu Kim

  DOI：10.1080/00397919608003689

  日期：1996.3

  Abstract A series of new 1, 2-O-isopropylidene-3-O-methyl-6-deoxy-6-N, N-dialkylamino-α-D-glucofuranoses 1 and 1, 2-O-isopropylidene-3, 6-dideoxy-6-N, N-dialkylamino-α-D-glucofuranoses 1′ were prepared from α-D-glucose and their enantiose-lectivities compared as chiral catalysts for the ethylation of benzaldehyde and heptanal with diethylzinc.

  摘要 一系列新的 1, 2-O-isopropylidene-3-O-methyl-6-deoxy-6-N, N-dialkylamino-α-D-glucofuranoses 1 and 1, 2-O-isopropylidene-3, 6-从 α-D-葡萄糖制备双脱氧-6-N, N-二烷基氨基-α-D-呋喃葡萄糖糖 1' 并将它们的对映糖选择性作为手性催化剂用于苯甲醛和庚醛与二乙基锌的乙基化反应。
• Oxydations et halogénations régiosélectives et réactions carbéniques de dérivés de sucres portant un groupement thioéther
  作者：Jean M. J. Tronchet、Hansjörg Eder

  DOI：10.1002/hlca.19800630104

  日期：1980.1.23

  Regioselective Oxidations, Regioselective Halogenations and Carbene Reactions of Sugar Derivatives Bearing a Thioether Group

  带有硫醚基的糖衍生物的区域选择性氧化，区域选择性卤化和卡宾反应
• Inversion of regioselectivity in reactions of diols through the use of hexamethylenestannylene acetals as intermediates
  作者：T.Bruce Grindley、Xianqi Kong

  DOI：10.1016/s0040-4039(00)73960-8

  日期：1993.8

  Hexamethylenestannylene acetals obtained from a variety of carbohydrate-derived terminal 1,2-diols give good to excellent regioselectivity for tosylation at the secondary oxygen. In contrast, non-cyclic dialkylstannylene acetals react mainly at the primary oxygen. These results are attributed to the greater stability of the dominant stannylene acetal dimers for hexamethylenestannylene acetals.
• Goueth, Pierre Y.; Ronco, Gino; Villa, Pierre, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 5, p. 679 - 696
  作者：Goueth, Pierre Y.、Ronco, Gino、Villa, Pierre

  DOI：——

  日期：——
• Kilaas, Lars; Anthonsen, Thorleif, Acta Chemica Scandinavica, 1992, vol. 46, # 10, p. 994 - 999
  作者：Kilaas, Lars、Anthonsen, Thorleif

  DOI：——

  日期：——