methyl 4-O-benzyl-2,3-di-O-methyl-6-O-p-tolylsulfonyl-α-D-glucopyranoside | 120123-44-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-benzyl-2,3-di-O-methyl-6-O-p-tolylsulfonyl-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-4,5,6-trimethoxy-3-phenylmethoxyoxan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 120123-44-6
• 化学式: C₂₃H₃₀O₈S
• 分子量: 466.552
• InChiKey: YUFBHHHQUVXVFJ-ZQGJOIPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  97.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 4-O-benzyl-2,3-di-O-methyl-6-O-p-tolylsulfonyl-α-D-glucopyranoside 在 4 A molecular sieve 、 四丁基碘化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium iodide 作用下， 生成 methyl 4-O-benzyl-6-deoxy-2,3-di-O-methyl-α-D-xylo-hex-5-enopyranoside
  参考文献：
  名称：

  Syntheses of 6-Deoxyhex-5-enopyranosides from 6-Bromo-6-deoxy- or 6-O-p-Tolylsulfonylhexopyranosides by the Use of DBU in DMSO

  摘要：

  各种非分支和甲基分支的6-脱氧己-5-烯吡喃苷衍生物是通过将6-溴-6-脱氧或6-O-对甲苯磺酰己吡喃苷与碘离子及1,8-二氮杂双环[5.4.0]十一烯在二甲基亚砜中进行连续处理，采用一锅法制备的。通过观察18种底物的反应，这一反应的范围和局限性变得明显。除了2,3-无水吡喃苷衍生物外，其他的反应产物（如altropyranoside和2-脱氧核糖己吡喃苷衍生物）产率较高。甲基分支的6-脱氧己-5-烯吡喃苷衍生物也以实用的产率获得。

  DOI：

  10.1246/bcsj.66.1156

文献信息

• An Efficient Deoxysugar Synthesis using Bu₄NBH₄via an S_N2 Reduction
  作者：Ken-ichi Sato、Toshio Hoshi、Yasuhiro Kajihara

  DOI：10.1246/cl.1992.1469

  日期：1992.8

  Deoxysugar derivatives were prepared from the corresponding triflate, tosylate, halogen, and epoxide derivatives. Employing the tetrabutylammonium tetrahydroborate reagent, the deoxygenation proceeds via an SN2 type displacement in good yield.

  脱氧糖衍生物由相应的三酸酯、对甲苯磺酸盐、卤素和环氧化物衍生物制备而成。利用四丁基四氢硼酸铵试剂，脱氧反应通过 SN2 型置换进行，收率很高。
• Convenient Synthesis of Hex-5-enopyranosides
  作者：Ken-ichi Sato、Noriyuki Kubo、Rituko Takada、Amjad Aqeel、Hironobu Hashimoto、Juji Yoshimura

  DOI：10.1246/cl.1988.1703

  日期：1988.10.5

  Hex-5-enopyranosides were prepared in an one-pot procedure from 6-bromo-6-deoxy- or 6-O-tosylhexopyranoside by the successive treatment with iodide anion and 1,8-diazabicyclo-[5.4.0]undec-7-ene in DMSO.

  通过在二甲基亚砜中连续处理碘离子和1,8-二氮杂双环[5.4.0]十一碳-7-烯，以一锅法从6-溴-6-脱氧-或6-O-对甲苯磺酰基己吡喃糖苷制备了六-5-烯吡喃糖苷。
• SATO, KEN-ICHI;KUBO, N.;TAKADA, R.;HASHIMOTO, H.;YOSHIMURA, J., CHEM. LETT.,(1988) N 10, C. 1703-1704
  作者：SATO, KEN-ICHI、KUBO, N.、TAKADA, R.、HASHIMOTO, H.、YOSHIMURA, J.

  DOI：——

  日期：——
• Syntheses of 6-Deoxyhex-5-enopyranosides from 6-Bromo-6-deoxy- or 6-<i>O</i>-<i>p</i>-Tolylsulfonylhexopyranosides by the Use of DBU in DMSO
  作者：Ken-ichi Sato、Noriyuki Kubo、Ritsuko Takada、Shogo Sakuma

  DOI：10.1246/bcsj.66.1156

  日期：1993.4

  Various kinds of nonbranched and methyl-branched 6-deoxyhex-5-enopyranoside derivatives were prepared from 6-bromo-6-deoxy or 6-O-p-tolylsulfonylhexopyranoside in a one-pot procedure by a successive treatment with iodide anion and 1,8-diazabicyclo[5.4.0]undec-7-ene in dimethyl sulfoxide. The scope and limitations of this reaction have become apparent by observing the reactions of 18 substrates. The yields of altropyranoside and 2-deoxyribo-hexopyranoside derivatives were high, except for the 2,3-anhydropyranoside derivative. Methyl-branched 6-deoxyhex-5-enopyranoside derivatives were also obtained in practical yields.

  各种非分支和甲基分支的6-脱氧己-5-烯吡喃苷衍生物是通过将6-溴-6-脱氧或6-O-对甲苯磺酰己吡喃苷与碘离子及1,8-二氮杂双环[5.4.0]十一烯在二甲基亚砜中进行连续处理，采用一锅法制备的。通过观察18种底物的反应，这一反应的范围和局限性变得明显。除了2,3-无水吡喃苷衍生物外，其他的反应产物（如altropyranoside和2-脱氧核糖己吡喃苷衍生物）产率较高。甲基分支的6-脱氧己-5-烯吡喃苷衍生物也以实用的产率获得。