3,4-di-O-acetyl-1,6-anhydro-2-deoxy-2-iodo-β-D-glucopyranose | 136573-62-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 3,4-di-O-acetyl-1,6-anhydro-2-deoxy-2-iodo-β-D-glucopyranose
• 英文别名: 3,4-Di-O-acetyl-1,6-anhydro-2-deoxy-2-iodo-b-D-glucopyranose；[(1R,2R,3S,4R,5R)-3-acetyloxy-4-iodo-6,8-dioxabicyclo[3.2.1]octan-2-yl] acetate
• CAS: 136573-62-1
• 化学式: C₁₀H₁₃IO₆
• 分子量: 356.114
• InChiKey: MQUXWUROYAWMGV-VVULQXIFSA-N

物化性质

• 沸点：
  376.1±42.0 °C(Predicted)
• 密度：
  1.79±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4-di-O-acetyl-1,6-anhydro-2-deoxy-2-iodo-β-D-glucopyranose 在 N-溴代丁二酰亚胺(NBS) 、 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 水 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 9.0h， 生成
  参考文献：
  名称：

  An electrophile-mediated cyclization on the 1,6-anhydro-d-glucopyranose framework

  摘要：

  Iodocyclization of O-tributylstannyl-D-glucal with iodine in acetonitrile gave 1,6-anhydro-2-deoxy-2-iodo-beta-D-glucopyranose (1) in high yield. The 3,4-di-O-acetyl derivative of 1 could be converted into the corresponding 2-deoxy compound and into the 2-C-allyl-2-deoxy branched sugar (5) by treatment with tributylstannane and allyltributylstannane, respectively. Controlled alkaline hydrolysis of 5 gave the 4-monoacetyl derivative. Complete hydrolysis of 5 gave the 3,4-diol, which underwent a 5-exo cyclization by treatment with N-bromosuccinimide. H-1 NMR spectroscopy and X-ray analysis showed that the cyclized product has the B3,O conformation in its pyranose ring, which is trans-fused to the newly formed tetrahydrofuran ring.

  DOI：

  10.1016/0008-6215(93)80026-b
• 作为产物：
  描述：

  6-O-(叔丁基二甲基硅烷基)-D-葡萄烯糖 在 吡啶 、 iodonium(di-γ-collidine) perchlorate 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 3,4-di-O-acetyl-1,6-anhydro-2-deoxy-2-iodo-β-D-glucopyranose
  参考文献：
  名称：

  Mereyala, Hari Babu; Venkataramanaiah, Kanamarlapudi C, Journal of Chemical Research, Miniprint, 1991, # 8, p. 1953 - 1966

  摘要：

  DOI：

文献信息

• Water Compatible Hypophosphites-<i>d</i>₂ Reagents: Deuteration Reaction via Deutero-deiodination in Aqueous Solution
  作者：Zejin Song、Jing Zeng、Ting Li、Xiang Zhao、Jing Fang、Lingkui Meng、Qian Wan

  DOI：10.1021/acs.orglett.0c00001

  日期：2020.3.6

  conventional deuteration approaches which typically entail deuterated solvents and/or moisture exclusion, an unprecedented deutero-deiodination reaction attainable in aqueous (H2O) solution is presented herein. By utilizing the stability of inorganic deuterated calcium/sodium hypophosphites against wayward H/D isotopic exchange within pH 2.5-11.7, these shelf-stable, nontoxic, cost-effective, and environmentally

  与通常需要氘代溶剂和/或排除水分的常规氘代方法相反，本文提出了在水溶液（H 2 O）中可获得的前所未有的氘代-碘化反应。通过利用无机氘化次磷酸钙/次磷酸钠的稳定性在pH 2.5-11.7范围内对抗随意的H / D同位素交换，这些耐贮存，无毒，经济高效且对环境有益的氘化试剂可介导各种烷基碘和芳基碘的氘代在水（H2O）溶液中加入足够的同位素。
• New reductive deiodination reaction by hydrogen atom transfer from cyclohexane
  作者：Jean Boivin、Béatrice Quiclet-Sire、Laure Ramos、Samir Z. Zard

  DOI：10.1039/a607459f

  日期：——

  Secondary iodides flanked by one or more inductive electron-withdrawing groups can be reduced via a radical chain reaction involving a hydrogen atom transfer from cyclohexane, the process being triggered by a small amount of an initiator such as dilauroyl peroxide.

  次级碘化物两侧有一个或多个诱导性电子吸引基团，可通过自由基链式反应进行还原，该反应涉及从环己烷转移一个氢原子，该过程由少量引发剂（如过氧化二月桂酰）引发。
• An electrophile-mediated cyclization on the 1,6-anhydro-d-glucopyranose framework
  作者：Christine Leteux、Alain Veyrières、Francis Robert

  DOI：10.1016/0008-6215(93)80026-b

  日期：1993.4

  Iodocyclization of O-tributylstannyl-D-glucal with iodine in acetonitrile gave 1,6-anhydro-2-deoxy-2-iodo-beta-D-glucopyranose (1) in high yield. The 3,4-di-O-acetyl derivative of 1 could be converted into the corresponding 2-deoxy compound and into the 2-C-allyl-2-deoxy branched sugar (5) by treatment with tributylstannane and allyltributylstannane, respectively. Controlled alkaline hydrolysis of 5 gave the 4-monoacetyl derivative. Complete hydrolysis of 5 gave the 3,4-diol, which underwent a 5-exo cyclization by treatment with N-bromosuccinimide. H-1 NMR spectroscopy and X-ray analysis showed that the cyclized product has the B3,O conformation in its pyranose ring, which is trans-fused to the newly formed tetrahydrofuran ring.
• Mereyala, Hari Babu; Venkataramanaiah, Kanamarlapudi C, Journal of Chemical Research, Miniprint, 1991, # 8, p. 1953 - 1966
  作者：Mereyala, Hari Babu、Venkataramanaiah, Kanamarlapudi C

  DOI：——

  日期：——