methyl 6-deoxy-6-iodo-2,3,4-tri-O-benzoyl-α-D-glucopyranoside | 34340-06-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-deoxy-6-iodo-2,3,4-tri-O-benzoyl-α-D-glucopyranoside
• 英文别名: methyl 6-iodo-2,3,4-tri-O-benzoyl-α-D-glucopyranoside；methyl 2,3,4-tri-O-benzoyl-6-deoxy-6-iodo-α-D-glucopyranoside；methyl 2,3,4-O-benzoyl-6-iodo-α-D-glucopyranoside；methyl-[tri-O-benzoyl-6-iodo-6-deoxy-α-D-glucopyranoside；Methyl-[tri-O-benzoyl-6-jod-6-desoxy-α-D-glucopyranosid；[(2S,3S,4S,5R,6S)-4,5-dibenzoyloxy-2-(iodomethyl)-6-methoxyoxan-3-yl] benzoate
• CAS: 34340-06-2
• 化学式: C₂₈H₂₅IO₈
• 分子量: 616.406
• InChiKey: PZIHVRKLNUFQQX-NRUNVSGISA-N

物化性质

• 熔点：
  99-100.5 °C
• 沸点：
  674.2±55.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 6-deoxy-6-iodo-2,3,4-tri-O-benzoyl-α-D-glucopyranoside 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 28.0h， 生成
  参考文献：
  名称：

  Structure‐Activity Relationships of Glucose‐based PdII‐Bis(NHC) Complexes in a Model Suzuki‐Miyaura Reaction

  摘要：

  The authors of this work have optimized a novel synthetic route towards glucose‐based PdII‐bis(NHC) complexes in only 4 steps with total yields up to 73 %. The synthesis route encompasses an Appel reaction towards 6‐iodo‐glucopyranosides, followed by acyl‐protection, then quaternization with imidazoles and finally the conversion of these acyl‐protected glucosyl imidazolium salts to their respective palladium(II)bis(NHC) complexes, via an intermediary silver(I) complex. Overall, 11 acyl‐protected glucosyl imidazolium iodides as NHC‐precursors and 15 complexes have been synthesized. The structure‐activity relationships of different functionalizations in these complexes and their reactivity in a model Suzuki‐Miyaura between bromobenzene and 4‐tolueneboronic acid reaction has been investigated, and a highly reactive complex leading to >99 % yield at 0.005 mol% catalytic loading has been found.

  DOI：

  10.1002/ejoc.202400177
• 作为产物：
  描述：

  alpha-甲基葡萄糖甙 在 吡啶 、 咪唑 、 三苯基膦 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 20.0h， 生成 methyl 6-deoxy-6-iodo-2,3,4-tri-O-benzoyl-α-D-glucopyranoside
  参考文献：
  名称：

  ω-不饱和亚硝基的分子内1,3-偶极环加成的多羟基化9-Oxa-1-氮杂双环[4.2.1]壬烷的单一非对映异构体

  摘要：

  从包含2-（苄氧基）乙醛的分子内1,3-偶极环加成反应中制备了8-苄氧基甲基-3,4,5-三苯甲酰氧基-9-氧杂-1-氮杂双环[4.2.1]壬烷作为单一的非对映异构体8。衍生自甲基α- d-吡喃葡萄糖苷的ω-不饱和羟胺7。以类似的方式，由d-吡喃半乳糖苷甲基和乙醛酸甲酯以非对映异构体15和16的3∶1混合物形式提供类似的8-甲氧基羰基9-氧杂-1-氮杂双环[4.2.1]壬烷。当在非手性离子液体17中进行时，该比例增加至8：1，而在手性离子液体18中则为化合物15 是专门成立的。

  DOI：

  10.1021/jo061503b

文献信息

• Preparation of glycosyl disulfides and sulfides via the formation of glycosyl Bunte salts as thiol surrogates
  作者：Monalisa Kundu、Anup Kumar Misra

  DOI：10.1016/j.tet.2021.132242

  日期：2021.5

  odourless reaction condition has been developed for the preparation of symmetrical glycosyl disulfide derivatives and aryl glycosyl disulfide derivatives from corresponding glycosyl iodides via formation of glycosyl Bunte salts as thiol surrogates. The reaction has been further extended towards the preparation of glycosyl sulfides derivatives from corresponding Bunte salt in the presence of sodium sulphide

  开发了一种方便的无味反应条件，用于从相应的糖基碘通过形成糖基邦特盐作为硫醇替代物来制备对称糖基二硫醚衍生物和芳基糖基二硫醚衍生物。该反应已进一步扩展到在硫化钠存在下从相应的邦特盐制备糖基硫醚衍生物。大多数反应产率高，适合放大生产。
• Palladium chloride mediated rearrangement of 6-deoxyhex-5-enopyranosides into cyclohexanones
  作者：Takamasa Iimori、Hideyo Takahashi、Shiro Ikegami

  DOI：10.1016/0040-4039(95)02223-6

  日期：1996.1

  PdCl2 was found to mediate the Ferrier rearrangement of broad range of substrates catalytically in neutral conditions. In this reaction, the stereoselectivity of newly formed chiral center was controlled by the hydroxyl protective groups on the starting sugar moiety and was rationally explained by the consideration of chair like conformations.

  发现PdCl 2在中性条件下催化介导大范围底物的Ferrier重排。在该反应中，新形成的手性中心的立体选择性受起始糖部分上的羟基保护基控制，并通过考虑椅子样构象得到合理解释。
• On-water synthesis of glycosyl selenocyanate derivatives and their application in the metal free organocatalytic preparation of nonglycosidic selenium linked pseudodisaccharide derivatives
  作者：Tapasi Manna、Anup Kumar Misra

  DOI：10.1039/d1ra00711d

  日期：——

  Glycosyl selenocyanate derivatives were prepared in very good yield by the treatment of glycosyl halide or triflate derivatives with potassium selenocyanate in water. A variety of selenium linked pseudodisaccharide derivatives were prepared in excellent yield using glycosyl selenocyanates as stable building blocks in the presence of hydrazine hydrate under metal-free organocatalytic reaction conditions

  通过用硒氰酸钾在水中处理糖基卤化物或三氟甲磺酸酯衍生物，以非常好的产率制备了糖基硒氰酸酯衍生物。在水合肼存在下，在无金属有机催化反应条件下，使用糖基硒氰酸酯作为稳定的结构单元，以优异的产率制备了多种硒连接的假二糖衍生物。
• Synthesis of unsymmetrical glycosyl diselenides by the treatment of symmetrical diselenides with glycosyl selenocyanates
  作者：Tapasi Manna、Abhijit Rana、Anup Kumar Misra

  DOI：10.1016/j.tet.2021.132358

  日期：2021.8

  A novel reaction condition has been developed for the synthesis of unsymmetrical glycosyl diselenide derivatives in excellent yield by the reaction of glycosyl selenocyanates as selenol surrogates with symmetrical diselenides in the presence of hydrazine monohydrate at room temperature. The reaction metal-free condition is reasonably fast, simple, non-malodorous and suitable for scale-up.

  已经开发了一种新的反应条件，用于在室温下在一水合肼的存在下，通过作为硒醇替代物的糖基硒氰酸酯与对称二硒化物反应，以优异的收率合成不对称糖基二硒化物衍生物。无金属反应条件相当快、简单、无臭，适合放大。
• Reductive Ring Opening of 6-Deoxy-6-iodopyranosides and 5-Deoxy-5-iodofuranosides by Manganese. A Convenient Procedure for the Preparation of Chiral 5-Hexenals and 4-Pentenals
  作者：Kazuho Tanaka、Shinjiro Yamano、Oyo Mitsunobu

  DOI：10.1055/s-2001-17476

  日期：——

  Reaction of fully protected 6-iodopyranosides and 5-iodofuranosides with Mn in the presence of trimethylsilyl chloride and PbCl2 (Takai-conditions) afforded the corresponding 5-hexenals and 4-pentenals in good to moderate yields.

  在三甲基氯硅烷和氯化铅（高井条件）存在下，完全保护的 6-碘吡喃糖苷和 5-碘呋喃糖苷与锰反应，可以得到相应的 5-己烯和 4-戊烯，收率从好到中等。