(3S,4R,5R)-3,4,5-Tris-benzyloxy-1-((2R,3R,5R,6S)-3,5-dihydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl)-hexan-1-one | 291282-30-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4R,5R)-3,4,5-Tris-benzyloxy-1-((2R,3R,5R,6S)-3,5-dihydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl)-hexan-1-one
• 英文别名: (3S,4R,5R)-1-[(2R,3R,5R,6S)-3,5-dihydroxy-6-methoxy-2-methyloxan-3-yl]-3,4,5-tris(phenylmethoxy)hexan-1-one
• CAS: 291282-30-9
• 化学式: C₃₄H₄₂O₈
• 分子量: 578.703
• InChiKey: PHRXQBARSLTETH-VOXZYPSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3S,4R,5R)-3,4,5-Tris-benzyloxy-1-((2R,3R,5R,6S)-3,5-dihydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl)-hexan-1-one 在 palladium on activated charcoal sodium tetrahydroborate 、 甲酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 methyl α-D-caryophylloside
  参考文献：
  名称：

  Synthesis of caryophyllose. Use of n-BuLi/Na-O-t-Bu in the coupling of highly functionalized ketones and dithioacetals

  摘要：

  The C-4 branched monosaccharide caryophyllose 2a was synthesized by a convergent approach relying on the coupling of metalated dithioacetal 4b with ketone 3. Combined use of n-BuLi and t-Bu-ONa as deprotonation system for 4b turned out to be decisive for the success off this coupling. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00752-8
• 作为产物：
  描述：

  methyl 2-O-tert-butyldimethylsilyl-3,6-dideoxy-α-D-erythro-hexopyranosid-4-ulose 在 正丁基锂 、 四丁基氟化铵 、 mercury dichloride 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 正己烷 、 水 、 乙腈 为溶剂， 反应 9.67h， 生成 (3S,4R,5R)-3,4,5-Tris-benzyloxy-1-((2R,3R,5R,6S)-3,5-dihydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl)-hexan-1-one
  参考文献：
  名称：

  Synthesis of caryophyllose. Use of n-BuLi/Na-O-t-Bu in the coupling of highly functionalized ketones and dithioacetals

  摘要：

  The C-4 branched monosaccharide caryophyllose 2a was synthesized by a convergent approach relying on the coupling of metalated dithioacetal 4b with ketone 3. Combined use of n-BuLi and t-Bu-ONa as deprotonation system for 4b turned out to be decisive for the success off this coupling. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00752-8

文献信息

• Synthesis of caryophyllose. Use of n-BuLi/Na-O-t-Bu in the coupling of highly functionalized ketones and dithioacetals
  作者：Matteo Adinolfi、Gaspare Barone、Pasquale Festa、Luigi Guariniello、Alfonso Iadonisi

  DOI：10.1016/s0040-4039(00)00752-8

  日期：2000.6

  The C-4 branched monosaccharide caryophyllose 2a was synthesized by a convergent approach relying on the coupling of metalated dithioacetal 4b with ketone 3. Combined use of n-BuLi and t-Bu-ONa as deprotonation system for 4b turned out to be decisive for the success off this coupling. (C) 2000 Elsevier Science Ltd. All rights reserved.