Methyl-<2,3-di-O-methyl-6-O-tosyl-α-D-glucopyranosid> | 25019-43-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl-<2,3-di-O-methyl-6-O-tosyl-α-D-glucopyranosid>
• 英文别名: Methyl-2,3-di-O-methyl-6-O-tosyl-α-D-glucopyranosid；[(2R,3R,4S,5R,6S)-3-hydroxy-4,5,6-trimethoxyoxan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 25019-43-6
• 化学式: C₁₆H₂₄O₈S
• 分子量: 376.428
• InChiKey: QFLMHYWUIJBZMM-LJIZCISZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  Methyl-<2,3-di-O-methyl-6-O-tosyl-α-D-glucopyranosid> 在 lithium aluminium tetrahydride 作用下， 生成 methyl 6-deoxy-2,3-di-O-methyl-α-D-glucopyranoside
  参考文献：
  名称：

  Stereoselective Mannich-Like Reactions of Ester Enolates Generated on Sugar Templates: A Novel Access to a Key Intermediate for 1β-Methylcarbapenem Synthesis

  摘要：

  DOI：

  10.3987/com-06-s(k)9
• 作为产物：
  描述：

  methyl 4,6-O-isopropylidene-2,3-di-O-methyl-α-D-glucopyranoside 以 吡啶 、 溶剂黄146 为溶剂， 反应 7.0h， 生成 Methyl-<2,3-di-O-methyl-6-O-tosyl-α-D-glucopyranosid>
  参考文献：
  名称：

  Synthesis of monosaccharide-fused azetidines

  摘要：

  Primary amines reacted upon 4,6-ditosylates of glucopyranosides to give an azetidine ring fused on C-4 and C-6 of the pyranose ring. On the other hand, the 4,6-ditosylate of benzyl mannopyranoside led to the 4,6-diamino-4,6-dideoxy derivative in a good yield. All the compounds and their precursors were identified by H-1 and C-13 NMR spectroscopy. Assignments of proton signals were made unambiguously using homodecoupling experiments. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00015-3

文献信息

• Diastereoselective reduction of chiral N-tosyl 2-Benzoyl-1,3-oxazines derived from D-glucose
  作者：Kwang-Youn Ko、Jong-Yek Park

  DOI：10.1016/s0040-4039(96)02311-8

  日期：1997.1

  Stereochemistry of reduction of the diastereomerically pure N-tosyl 2-benzoyl-1,3-oxazines prepared from D-glucose was investigated with various reducing agents. It was found that the stereochemical outcome is consistent with the Cram's chelation model where the ring oxygen atom is involved in chelation, not the tosyl oxygen as in the 5-membered oxazolidines.

  用各种还原剂研究了由D-葡萄糖制备的非对映体纯的N-甲苯磺酰基2-苯甲酰基-1,3-恶嗪还原的立体化学。发现立体化学结果与克拉姆的螯合模型一致，在该模型中，环氧原子参与了螯合，而不是如五元恶唑烷中的甲苯磺酰氧。
• Fuerstner, Alois; Baumgartner, Judith; Jumbam, Denis N., Journal of the Chemical Society. Perkin transactions I, 1993, # 1, p. 131 - 138
  作者：Fuerstner, Alois、Baumgartner, Judith、Jumbam, Denis N.

  DOI：——

  日期：——
• SHONO, TATSUYA;MATSUMURA, YOSHIHIRO;HAMAGUCHI, HIROSHI;NAITOH, SHIGEKI, J. ORG. CHEM., 1983, 48, N 25, 5126-5128
  作者：SHONO, TATSUYA、MATSUMURA, YOSHIHIRO、HAMAGUCHI, HIROSHI、NAITOH, SHIGEKI

  DOI：——

  日期：——
• Synthesis of monosaccharide-fused azetidines
  作者：Thierry Michaud、Josette Chanet-Ray、Sithan Chou、Jacques Gelas

  DOI：10.1016/s0008-6215(97)00015-3

  日期：1997.4

  Primary amines reacted upon 4,6-ditosylates of glucopyranosides to give an azetidine ring fused on C-4 and C-6 of the pyranose ring. On the other hand, the 4,6-ditosylate of benzyl mannopyranoside led to the 4,6-diamino-4,6-dideoxy derivative in a good yield. All the compounds and their precursors were identified by H-1 and C-13 NMR spectroscopy. Assignments of proton signals were made unambiguously using homodecoupling experiments. (C) 1997 Elsevier Science Ltd.
• Stereoselective Mannich-Like Reactions of Ester Enolates Generated on Sugar Templates: A Novel Access to a Key Intermediate for 1β-Methylcarbapenem Synthesis
  作者：Kin-ichi Tadano、Daisuke Sasaki、Daisuke Sawamoto、Ken-ichi Takao、Masayuki Okue、Keiichi Ajito

  DOI：10.3987/com-06-s(k)9

  日期：——