3,4,6-tri-O-benzyl-2-(tri-n-butylstannyl)-D-glucal | 105938-01-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4,6-tri-O-benzyl-2-(tri-n-butylstannyl)-D-glucal
• 英文别名: tributylstannyl 3,4,6-tri-O-benzyl-D-glucal
• CAS: 105938-01-0
• 化学式: C₃₉H₅₄O₄Sn
• 分子量: 705.565
• InChiKey: CWZNBUWZZFSNHE-GFXHWERGSA-N

物化性质

• 沸点：
  687.7±65.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.04
• 重原子数：
  44
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-benzyl-2-(tri-n-butylstannyl)-D-glucal 在 sodium hydroxide 、 四(三苯基膦)钯 、 dimethyl sulfide borane 、 双氧水 作用下， 以 甲苯 为溶剂， 生成 (3,4,6-tri-O-benzyl-β-D-glucopyranosyl)methylbenzene
  参考文献：
  名称：

  通过钯催化的三丁基锡烷基糖基与有机卤化物的偶联反应形成C-糖苷

  摘要：

  1-（三丁基锡烷基）-D-葡糖与不饱和卤化物的钯催化偶联反应提供了相应的1- C-烷基化的葡糖，这是1,3-二溴苯对称或不对称二C-糖基化的有效方法。

  DOI：

  10.1039/c39900001191
• 作为产物：
  描述：

  1,5-anhydro-3,4,6-tri-O-phenylmethyl-1,2-dideoxy-1-[(Ss)-phenylsulfinyl]-D-arabino-hex-1-enitol 、 三丁基氯化锡 在 苯基锂 作用下， 以 四氢呋喃 为溶剂， 生成 3,4,6-tri-O-benzyl-2-(tri-n-butylstannyl)-D-glucal
  参考文献：
  名称：

  Synthesis and Pd-catalyzed coupling of1-C-stannylated glycals

  摘要：

  1-Tributylstannyl glycals were applied as versatile tools in the Pd(0)-mediated synthesis of glycal phthalonitrile conjugates. Likewise, selective homo-coupling of 1-tributylstannyl glycals furnishing C1-C1' linked glycal dimers was investigated by using Pd(II)-species. For both Stille type couplings the rate-accelerating effect of copper(I) thiophene-2-carboxylate (CuTC) was exploited. The synthesis of stannylated glycal precursors was significantly improved by establishing a one-pot two-step procedure via glycosyl sulfoxides.

  DOI：

  10.1080/07328303.2018.1508590

文献信息

• Copper(I)-Mediated 1,2-Metallate Rearrangements of 1-Metallated Glycals
  作者：Philip Kocieński、Krzysztof Jarowicki、Zofia Komsta、Anna Wojtasiewicz

  DOI：10.1055/s-0031-1289721

  日期：2012.3

  1,2-Metallate rearrangements involving reaction of 1-metallated glycals with organolithium reagents under copper(I) mediation give alkenylpolyol chains in 45-91% yield (19 examples). The reaction was applied to a formal synthesis of KRN7000 as well as a synthesis of a Δ5,6-ceramide derivative. 1,2-metallate rearrangement - retro-[1,4]-Brook rearrangement - 1-metallated glycals - cuprates - organolithiums

  1,2-金属盐重排涉及1-金属化的缩醛与有机锂试剂在铜（I）介导下的反应，链烯基多元醇链的收率为45-91％（19个实例）。将反应物施加到KRN7000的合成正式以及一个Δ的合成5,6- -神经酰胺衍生物。 1,2-金属盐重排-Retro- [1,4] -Brook重排-1-金属化糖-铜酸盐-有机锂-KRN7000
• Synthesis of C-glycopyranosyl compounds by a palladium-catalyzed coupling reaction of 1-tributylstannyl-d-glucals with organic halides
  作者：Eric Dubois、Jean-Marie Beau

  DOI：10.1016/s0008-6215(00)90552-4

  日期：1992.4

  1-Tributylstannyl-D-glucals, prepared from the corresponding 1-phenylsulfonyl-D-glucals, were coupled efficiently to various organic halides in the presence of a palladium(0) catalyst. This mild reaction is specially useful for the preparation of 1-C-aryl-D-glucals and compatible with unprotected hydroxy groups or hindered aromatic bromides. It has been shown that the resulting 1-C-aryl(alkyl)-D-glucals

  由相应的1-苯基磺酰基-D-葡萄糖制备的1-三丁基锡烷基-D-葡萄糖在钯（0）催化剂的存在下有效地偶联到各种有机卤化物上。这种温和的反应对于制备1-C-芳基-D-葡萄糖特别有用，并且与未保护的羟基或受阻的芳香族溴化物相容。已经表明，所得的1-C-芳基（烷基）-D-葡萄糖适用于烯醇醚基团的进一步合成操作，包括立体选择性氢化，硼氢化-氧化或环氧化。所有形成的化合物都是由试剂对葡糖衍生物的α-面的攻击所致。反应扩展到1，3-，1，4-二-和1,3,5-三溴苯，导致相应的对称的二-（三）-C-葡萄糖基苯。最后，顺序的二-C-葡萄糖基化为1
• Synthesis of (6<i>R</i>,7<i>R</i>)-D-<i>gluco</i>-L-<i>gulo</i>-6,7-dodecodiulose-(6,2),(7,11)
  作者：Takashi Mochizuki、Masao Shiozaki

  DOI：10.1246/cl.1997.801

  日期：1997.8

  (6R,7R)-d-gluco-l-gulo-6,7-dodecodiulose-(6,2),(7,11) was synthesized from 3,4,6-tri-O-benzyl-1-stannyl-d-glucal via stereospecific addition reaction of lithioglucal to 2,3,4,6-tetra-O-benzyl-d-glucono-1,5-lactone.

  (6R,7R)-d-gluco-l-gulo-6,7-dodecodiulose-(6,2),(7,11) 是由 3,4,6-O-tri-benzyl-1-stannyl-d-glucal 通过石蒜醛与 2,3,4,6-tetra-O-benzyl-d-glucono-1,5-lactone 的立体加成反应合成的。
• Spiroketalization Reactions on a Carbohydrate Template
  作者：Peter Quayle、Jeremy C. Conway、Christopher J. Urch、Jie Xu

  DOI：10.1055/s-2006-933126

  日期：——

  Negishi and Stille coupling reactions of 3,4,6-tri-O-benzyl-2-(tri-n-butylstannyl)-d-glucal with (Z)-vinyl iodides provides access to functionalized spiroketals.

  3,4,6-三-O-苄基-2-(三正丁基锡烷基)-D-葡萄糖醛与（Z）-乙烯基碘化物的根岸-斯蒂尔偶联反应提供了功能化的螺酮的途径。
• Second generation benzannulation reactions: Sugar-derived Fischer chlorocarbene complexes in organic synthesis
  作者：Michael.R. Hallett、James E. Painter、Peter Quayle、Dean Ricketts、Prakash Patel

  DOI：10.1016/s0040-4039(98)00315-3

  日期：1998.4

  The facile metallation of 2-chloroglucal derivatives 8 and 11 affords ready access to the corresponding Fischer carbene complexes 10 and 13. Carbene complexes 10 and 13 undergo benzannulation reactions with acetylenes to provide functionalised benzopyrans in moderate overall yields.

  2-氯葡萄糖衍生物8和11的易金属化提供了对相应的Fischer卡宾配合物10和13的便捷访问。碳配合物10和13与乙炔进行苯并环化反应，以适中的总收率提供官能化的苯并吡喃。