(3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyl-5-[(Z)-2-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran | 183604-62-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyl-5-[(Z)-2-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran
• 英文别名: (1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-8-[(Z)-2-[(2S,3S,4R,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]ethenyl]-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecane
• CAS: 183604-62-8
• 化学式: C₄₇H₅₄O₁₀
• 分子量: 778.94
• InChiKey: IWZBMRHLTRKEDU-ZHRWJSPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  57
• 可旋转键数：
  15
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  92.3
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyl-5-[(Z)-2-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran 在 palladium dihydroxide 、 甲烷 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 以95%的产率得到(2R,3R,4R,5R,6S)-2-Hydroxymethyl-6-[2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethyl]-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  由C-甲酰基糖苷合成C-二糖

  摘要：

  C-甲酰基2,3：5,6-二-O-异亚丙基-d-呋喃呋喃糖苷（1）与2,3,4,6-四-O-苄基-d-吡喃半乳糖苷（2）之间的偶联半乳糖6-磷烷3生成相应的烯烃，这些烯烃在氢解后分别以56％和72％的收率得到β（1→6'）连接的C-二糖6和8。

  DOI：

  10.1016/0040-4039(96)01667-x
• 作为产物：
  描述：

  6-deoxy-1,2:3,4-di-O-isopropylidene-6-(triphenylphosphino)-α-D-galactopyranose iodide 、 (2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)methanal 在 正丁基锂 、 4 A molecular sieve 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 以76%的产率得到(3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyl-5-[(Z)-2-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran
  参考文献：
  名称：

  由C-甲酰基糖苷合成C-二糖

  摘要：

  C-甲酰基2,3：5,6-二-O-异亚丙基-d-呋喃呋喃糖苷（1）与2,3,4,6-四-O-苄基-d-吡喃半乳糖苷（2）之间的偶联半乳糖6-磷烷3生成相应的烯烃，这些烯烃在氢解后分别以56％和72％的收率得到β（1→6'）连接的C-二糖6和8。

  DOI：

  10.1016/0040-4039(96)01667-x

文献信息

• Synthesis of α- and β-<scp>d</scp>-(1→6)-<i>C</i>-Disaccharides by Wittig Olefination of Formyl <i>C</i>-Glycosides with Glycopyranose 6-Phosphoranes
  作者：Alessandro Dondoni、Helene M. Zuurmond、Alessia Boscarato

  DOI：10.1021/jo971177n

  日期：1997.11.1

  The synthesis of (1-->6)-C-disaccharides by Wittig condensation of formyl C-glycofuranosides and pyranosides with galacto-and glucopyranose B-phosphoranes is described herein. The method involves the coupling of the sugar aldehydes with the ylides and the reduction of the double bond of the resulting sugar alkenes, in most of the cases by catalytic hydrogenation. The reduction with nickel boride or diimide is employed in some special cases. O-Benzyl protective groups are removed by catalytic hydrogenation either in the course of the reduction of the double bond or in a subsequent step, while O-isopropylidene groups are cleaved by treatment with Amberlite IR-120. In this way, eight free beta-D-(1-->6)-C-disaccharides have been prepared in 26-61% overall yield starting from B-linked formyl C-glycosides. These include C-linked analogues of the biologically active disaccharides allolactose (Gal beta 1,6Glc), gentiobiose (Glc beta 1,6Glc), and N-acetylamino disaccharides (GalNHAc beta,6Gal and GalNHAc beta 1,6Glc). Moreover, the synthesis of two alpha-D-(1-->6)-C-disaccharides is described from formyl C-furanosides. The limiting condition of the synthesis of these stereoisomers is the configurational instability of the alpha-linked formyl C-glycosides under the basic conditions of the Wittig olefination.
• Synthesis of C-disaccharides from C-formyl glycosides
  作者：Alessandro Dondoni、Alessia Boscarato、Helene Zuurmond

  DOI：10.1016/0040-4039(96)01667-x

  日期：1996.10

  ranoside (1) and 2,3,4,6-tetra-O-benzyl-d-galactopyranoside (2) with the protected galactose 6-phosphorane 3 leads to the corresponding olefins which upon hydrogenolysis give β (1 →6′)-linked C-disaccharides 6 and 8 in 56 and 72% yield, respectively.

  C-甲酰基2,3：5,6-二-O-异亚丙基-d-呋喃呋喃糖苷（1）与2,3,4,6-四-O-苄基-d-吡喃半乳糖苷（2）之间的偶联半乳糖6-磷烷3生成相应的烯烃，这些烯烃在氢解后分别以56％和72％的收率得到β（1→6'）连接的C-二糖6和8。