6,7-O-Isopropylidene-2,3-dideoxy-D-ribo-heptono-1,4-lactone | 131530-77-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,7-O-Isopropylidene-2,3-dideoxy-D-ribo-heptono-1,4-lactone
• 英文别名: (5S)-5-((S)-[((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl])dihydrofuran-2-one；(5S)-5-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-hydroxymethyl]oxolan-2-one
• CAS: 131530-77-3
• 化学式: C₁₀H₁₆O₅
• 分子量: 216.234
• InChiKey: BFDHDTZKLKTVIF-OOZYFLPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6,7-O-Isopropylidene-2,3-dideoxy-D-ribo-heptono-1,4-lactone 在 2,6-二甲基吡啶 、 sodium periodate 、 silica gel 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (1S,4R,5S,6S)-5,6-bis-(tert-butyldimethylsilanyloxy)-2-oxabicyclo[2.2.1]heptan-3-one
  参考文献：
  名称：

  Variable Strategy toward Carbasugars and Relatives. 2.¹ Diversity-Based Synthesis of β-d-Xylo, β-d-Ribo, β-l-Arabino, and β-l-Lyxo 4a-Carbafuranoses and (4a-Carbafuranosyl)thiols

  摘要：

  The silyloxy diene-based construction of carbasugars, previously exploited for the synthesis of four carbocyclic furanose and pyranose analogues, has been investigated further. By introducing a novel silylative cycloaldolization protocol and by adjusting a couple of minor transformations, the efficiency of this synthetic sequence was greatly improved. Through a series of lactone/thiolactone aldehyde cyclization precursors, four carbafuranoses (4a-carba-beta -D-xylofuranose, 4a-carba-beta -D-ribofuranose, 4a-carba-beta -L-arabinofuranose, and 4a-carba-beta -L-lyxofuranose) and four (carbafuranosyl)thiols [(4a-carba-beta -D-xylofuranosyl)thiol, (4a-carba-beta -D-ribofuranosyl)thiol, (4a-carba-beta -L-arabinofuranosyl)thiol, and (4a-carba-beta -L-lyxofuranosyl)thiol] were assembled. From this study, it was shown that these constructions tolerate a variety of precursors, and in many instances, they are suitable for scaling-up.

  DOI：

  10.1021/jo010585v
• 作为产物：
  描述：

  (1'S,4''R,5R)-5-[(2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl]-5H-furan-2-one 在 sodium tetrahydroborate 、 三乙胺 、 nickel dichloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 6,7-O-Isopropylidene-2,3-dideoxy-D-ribo-heptono-1,4-lactone
  参考文献：
  名称：

  Variable Strategy toward Carbasugars and Relatives. 2.¹ Diversity-Based Synthesis of β-d-Xylo, β-d-Ribo, β-l-Arabino, and β-l-Lyxo 4a-Carbafuranoses and (4a-Carbafuranosyl)thiols

  摘要：

  The silyloxy diene-based construction of carbasugars, previously exploited for the synthesis of four carbocyclic furanose and pyranose analogues, has been investigated further. By introducing a novel silylative cycloaldolization protocol and by adjusting a couple of minor transformations, the efficiency of this synthetic sequence was greatly improved. Through a series of lactone/thiolactone aldehyde cyclization precursors, four carbafuranoses (4a-carba-beta -D-xylofuranose, 4a-carba-beta -D-ribofuranose, 4a-carba-beta -L-arabinofuranose, and 4a-carba-beta -L-lyxofuranose) and four (carbafuranosyl)thiols [(4a-carba-beta -D-xylofuranosyl)thiol, (4a-carba-beta -D-ribofuranosyl)thiol, (4a-carba-beta -L-arabinofuranosyl)thiol, and (4a-carba-beta -L-lyxofuranosyl)thiol] were assembled. From this study, it was shown that these constructions tolerate a variety of precursors, and in many instances, they are suitable for scaling-up.

  DOI：

  10.1021/jo010585v

文献信息

• The four-carbon elongation of three-carbon chiral synthons using 2-(trimethylsiloxy)furan: highly stereocontrolled entry to enantiomerically pure seven-carbon α,β-unsaturated 2,3-dideoxy-aldonolactones
  作者：Giovanni Casiraghi、Lino Colombo、Gloria Rassu、Pietro Spanu、Giovanna Gasparri Fava、Marisa Ferrari Belicchi

  DOI：10.1016/s0040-4020(01)87777-2

  日期：1990.1
• Variable Strategy toward Carbasugars and Relatives. 2.¹ Diversity-Based Synthesis of β-<scp>d</scp>-Xylo, β-<scp>d</scp>-Ribo, β-<scp>l</scp>-Arabino, and β-<scp>l</scp>-Lyxo 4a-Carbafuranoses and (4a-Carbafuranosyl)thiols
  作者：Gloria Rassu、Luciana Auzzas、Luigi Pinna、Vincenzo Zambrano、Lucia Battistini、Franca Zanardi、Lucia Marzocchi、Domenico Acquotti、Giovanni Casiraghi

  DOI：10.1021/jo010585v

  日期：2001.11.1

  The silyloxy diene-based construction of carbasugars, previously exploited for the synthesis of four carbocyclic furanose and pyranose analogues, has been investigated further. By introducing a novel silylative cycloaldolization protocol and by adjusting a couple of minor transformations, the efficiency of this synthetic sequence was greatly improved. Through a series of lactone/thiolactone aldehyde cyclization precursors, four carbafuranoses (4a-carba-beta -D-xylofuranose, 4a-carba-beta -D-ribofuranose, 4a-carba-beta -L-arabinofuranose, and 4a-carba-beta -L-lyxofuranose) and four (carbafuranosyl)thiols [(4a-carba-beta -D-xylofuranosyl)thiol, (4a-carba-beta -D-ribofuranosyl)thiol, (4a-carba-beta -L-arabinofuranosyl)thiol, and (4a-carba-beta -L-lyxofuranosyl)thiol] were assembled. From this study, it was shown that these constructions tolerate a variety of precursors, and in many instances, they are suitable for scaling-up.