3-O-(tert-Butyldimethylsilyl)-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexodialdo-1,4-furanose | 170872-97-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-(tert-Butyldimethylsilyl)-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexodialdo-1,4-furanose
• 英文别名: 2-[(3aR,5R,6S,6aR)-6-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]acetaldehyde
• CAS: 170872-97-6
• 化学式: C₁₅H₂₈O₅Si
• 分子量: 316.47
• InChiKey: VFWGFRDJZOFAMH-YVECIDJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	Methyl 3-O-(tert-butyldimethylsilyl)-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexafuranuronate	170873-00-4	C16H30O6Si	346.496
  ——	Methyl 3-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-5-O-(phenoxythiocarbonyl)-α-D-glucuronate	170872-99-8	C23H34O8SSi	498.67
  ——	D-glucurono-3,6-lactone acetonide	20513-98-8	C9H12O6	216.191
  ——	Methyl 1,2-O-isopropylidene-5-O-(phenoxythiocarbonyl)-α-D-glucuronate	170872-98-7	C17H20O8S	384.407
  ——	(+)-1,2-O-Isopropylidene-5-O-(phenoxythiocarbonyl)-α-D-glucurono-6,3-lactone	170872-96-5	C16H16O7S	352.365

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	10,11-Anhydro-3-O-(tert-butyldimethylsilyl)-5,7-dideoxy-1,2-O-isopropylidene-7-C-(methoxycarbonyl)-9-O-(methoxymethyl)-β-L-ido-L-ido-undecofuranose	——	C24H44O11Si	536.692
  ——	3-O-(tert-Butyldimethylsilyl)-10-chloro-5,7,10-trideoxy-1,2-O-isopropylidene-7-C-(methoxycarbonyl)-9-O-(methoxymethyl)-α-D-gluco-L-ido-undecofuranose	170873-17-3	C24H45ClO11Si	573.153
  ——	3,11-Di-O-(tert-butyldimethylsilyl)-10-chloro-5,7,10-trideoxy-1,2-O-isopropylidene-7-C-(methoxycarbonyl)-9-O-(methoxymethyl)-α-D-gluco-L-ido-undecofuranose	——	C30H59ClO11Si2	687.416
  ——	9,7-(Carboxy)-anhydro-3-O-(tert-butyldimethylsilyl)-7-C-carboxy-10-chloro-5,7,10-trideoxy-1,2-O-isopropylidene-α-D-gluco-L-ido-undecofuranose	——	C21H37ClO9Si	497.058
  ——	3-O-(tert-Butyldimethylsilyl)-10-chloro-5,7,10-trideoxy-6,8,11-tri-O-(triethylsilyl)-7-C-(hydroxymethyl)-1,2-O-isopropylidene-9-O-(methoxymethyl)-α-D-gluco-L-ido-undecofuranose	170873-22-0	C41H87ClO10Si4	887.931
  ——	3-O-(tert-Butyldimethylsilyl)-10-chloro-5,7,10-trideoxy-6,8,11-tri-O-(triethylsilyl)-1,2-O-isopropylidene-9-O-(methoxymethyl)-7-C-methylidene-α-D-arabino-L-ido-undecofuranose	170873-23-1	C41H85ClO9Si4	869.915
  ——	3-O-(tert-Butyldimethylsilyl)-10-chloro-5,7,10-trideoxy-6,8,11-tri-O-(triethylsilyl)-1,2-O-isopropylidene-7-C-(methoxycarbonyl)-9-O-(methoxymethyl)-α-D-gluco-L-ido-undecofuranose	——	C42H87ClO11Si4	915.941
  ——	(6R)-3-O-(tert-Butyldimethylsilyl)-6-C-<(1'R,3'S,4'R,5'S,6'S)-6'-endo-chloro-5'-endo-(methoxymethoxy)-2'-oxo-7'-oxabicyclo<2.2.1>hept-3'-exo-yl>-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose	170873-15-1	C23H39ClO9Si	523.096
  ——	(6R)-3-O-(tert-Butyldimethylsilyl)-6-C-<(1'S,4'S,5'R,6'S,7'S)-7'-endo-chloro-6'-endo-(methoxymethoxy)-3'-oxo-2',8'-dioxabicyclo<3.2.1>oct-4'-exo-yl>-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose	170873-14-0	C23H39ClO10Si	539.095
  ——	(7RS)-6,10-Anhydro-5-deoxy-1,2-O-isopropylidene-9-O-(methoxymethyl)-α-D-arabino-L-ido-7-undeculofuranose-(1,4)-pyranose-(7,3)	——	C16H26O10	378.376

反应信息

• 作为反应物：
  描述：

  3-O-(tert-Butyldimethylsilyl)-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexodialdo-1,4-furanose 在 吡啶 、 sodium tetrahydroborate 、 正丁基锂 、 三丁基膦 、 sodium methylate 、 二异丁基氢化铝 、 cesium fluoride 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 45.59h， 生成 10,11-Anhydro-5,7-dideoxy-1,2-O-isopropylidene-9-O-(methoxymethyl)-7-C-<<(2-nitrophenyl)seleno>methyl>-β-L-ido-L-ido-undecofuranose
  参考文献：
  名称：

  Synthesis of Undeculofuranoside Derivatives of the Herbicidins and of Analogs

  摘要：

  The condensation of 3-O-(tert-butyldimethylsilyl)-5-deoxy-1,2-O-isopropylidene-alpha-D-xylo-hexodialdo-1,4-furanose (obtained in six steps (35%) from D-glucurono-6,3-lactone) with the lithium enolate of (+/-)6-endo-chloro-5-endo-(methoxymethoxy)-7-oxabicyclo[2.2.1]heptan-2-one (derived in six steps (25%) from the Diels-Alder adduct of furan to 1-cyanovinyl acetate) was highly exo face selective giving two major aldols that were separated readily. One of them was converted to 6,10-anhydro-5-deoxy-1,2-O-isopropylidene-9-O-(methoymethyl)-alpha-D-arabino-L-ido-7-undeculofuranose-(1,4)-pyranose-(7,3), a semiprotected form of the long-chain carbohydrate moiety of the herbicidins. The synthesis implies the acid-promoted isomerization of 10,11-anhydro-5,7-dideoxy-1,2-O-isopropylidene-9-O-(methoxymethyl)-7-C-[(2-nitrophenyl)selenomethyl]-beta-L-ido-L-ido-undecofuranose.

  DOI：

  10.1021/jo00123a021
• 作为产物：
  描述：

  D-glucurono-3,6-lactone acetonide 在 吡啶 、 2,6-二甲基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 二异丁基氢化铝 、 sodium cyanoborohydride 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 9.0h， 生成 3-O-(tert-Butyldimethylsilyl)-5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexodialdo-1,4-furanose
  参考文献：
  名称：

  Synthesis of Undeculofuranoside Derivatives of the Herbicidins and of Analogs

  摘要：

  The condensation of 3-O-(tert-butyldimethylsilyl)-5-deoxy-1,2-O-isopropylidene-alpha-D-xylo-hexodialdo-1,4-furanose (obtained in six steps (35%) from D-glucurono-6,3-lactone) with the lithium enolate of (+/-)6-endo-chloro-5-endo-(methoxymethoxy)-7-oxabicyclo[2.2.1]heptan-2-one (derived in six steps (25%) from the Diels-Alder adduct of furan to 1-cyanovinyl acetate) was highly exo face selective giving two major aldols that were separated readily. One of them was converted to 6,10-anhydro-5-deoxy-1,2-O-isopropylidene-9-O-(methoymethyl)-alpha-D-arabino-L-ido-7-undeculofuranose-(1,4)-pyranose-(7,3), a semiprotected form of the long-chain carbohydrate moiety of the herbicidins. The synthesis implies the acid-promoted isomerization of 10,11-anhydro-5,7-dideoxy-1,2-O-isopropylidene-9-O-(methoxymethyl)-7-C-[(2-nitrophenyl)selenomethyl]-beta-L-ido-L-ido-undecofuranose.

  DOI：

  10.1021/jo00123a021