methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-nitro-β-D-hex-2-enepyranoside | 61664-96-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-nitro-β-D-hex-2-enepyranoside
• 英文别名: (2R,4aR,6R,8aS)-6-methoxy-8-nitro-2-phenyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine
• CAS: 61664-96-8
• 化学式: C₁₄H₁₅NO₆
• 分子量: 293.276
• InChiKey: LUKNPLGKZJKOPN-YIYPIFLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  82.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-nitro-β-D-hex-2-enepyranoside 在 sodium hydroxide 、 双氧水 、 十六烷基三丁基溴化磷 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 水 、 甲苯 为溶剂， 反应 4.08h， 生成 (1R,2S,4S,5R,7R,10R)-5-methoxy-10-phenyl-3,6,9,11-tetraoxatricyclo[5.4.0.02,4]undecane-4-carboxamide
  参考文献：
  名称：

  Preparation of 2-C- and 3-C-cyano-2-enopyranoside derivatives and their epoxidation

  摘要：

  Methyl 4,6-O-benzylidene-2-C- and 3-C-cyano-2,3-dideoxy-D-erythro-hex-2-enopyranosides and -2-enitols were prepared and their epoxidation was performed. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.07.008

文献信息

• Stereochemistry of nucleophilic addition reactions 13
  作者：Tohru Sakakibara、Yoshifusa Tachmori、Rokuro Sudoh

  DOI：10.1016/s0040-4020(01)91801-0

  日期：1984.1

  An improved synthesis of methyl 4,6-0-benzylidene-2,3-dideoxy-2-nitro-β-D-erythro-hex-2-enopyranoside and its reactions with various nucleophiles are described; all the nucleophiles were found to approach exclusively or predominantly from the equatorial side of the molecule, giving the β-D-glucopyranoside derivatives as the major or exclusive product. The stereochemical course of approach of a nucleophile

  描述了一种改进的甲基4,6-0-亚苄基-2,3-二脱氧-2-硝基-β-D-赤型-己基-2-烯吡喃糖苷的合成及其与各种亲核试剂的反应。发现所有亲核试剂都接近或主要从分子的赤道侧接近，从而以β-D-吡喃葡萄糖苷衍生物为主要或专有产物。讨论了在本反应和文献中观察到的亲核试剂的立体化学过程。
• Experimental and Theoretical (AM1) Studies on Photoaddition Reactions of 3-Nitro-2-enopyranoside Derivatives.
  作者：Tohru Sakakibara、Ichiro Matuo、Aya Takaide、Takanori Nakamura、Akinori Seta

  DOI：10.1246/cl.1992.177

  日期：——

  3-nitro-α- and β-D-erythro-hex-2-enopyranoside derivatives in methanol, ethanol, and isopropanol with high pressure Hg lamp gave the adducts in moderate yields. The stereoselectivities calculated by AM1 calculation by the use of model compounds with 1,3-dioxolan-2-yl radical are not conflict with those observed in similar photoreaction in 1,3-dioxolane as well as the present results

  用高压汞灯照射甲醇、乙醇和异丙醇中的 3-硝基-α-和 β-D-erythro-hex-2-enopyranoside 衍生物，得到中等产率的加合物。使用具有 1,3-dioxolan-2-yl 自由基的模型化合物通过 AM1 计算计算的立体选择性与在 1,3-dioxolane 中类似光反应中观察到的立体选择性以及目前的结果没有冲突
• Synthesis of hybrids of d-glucose and d-galactose with 1-deoxynojirimycin analogues using ring-closing metathesis
  作者：Amit Kumar、Girish K. Rawal、Yashwant D. Vankar

  DOI：10.1016/j.tet.2008.01.005

  日期：2008.3

  Four hybrids of azasugars with d-glucose and d-galactose have been synthesized from 3-nitro-2,3-unsaturated-O-glycosides. All the hybrid molecules showed moderate activity against β-galactosidase, the one derived from d-glucose and 1,4-dideoxygulonojirimycin 18, and 26, which is a hybrid of d-glucose and 1,4-dideoxymannohomonojrimycin, showed selectivity toward α-glucosidase and β-galactosidase, respectively

  氮杂糖与d-葡萄糖和d-半乳糖的四个杂种已经从3-硝基-2,3-不饱和-O-糖苷合成。所有的杂交分子显示出对β半乳糖苷酶，从d-葡萄糖和1,4- dideoxygulonojirimycin导出的一个适度活动18，和26，其是d-葡萄糖和1,4- dideoxymannohomonojrimycin的混合体，表现出对α-选择性葡萄糖苷酶和β-半乳糖苷酶。
• Preparation of methyl 4,6-di-O-acetyl-3-C-nitro-2-enopyranoside derivatives and their reduction with sodium borodeuteride
  作者：Akinori Seta、Kiohisa Tokuda、Miki Kaiwa、Tohru Sakakibara

  DOI：10.1016/0008-6215(95)00341-x

  日期：1996.2

  attacks exclusively from the side opposite of the anomeric methoxyl group. However, the stereoselectivity of a similar reduction of the corresponding 4,6-O- benzylidene -β- d -threo-2- enopyranoside derivative, adopting the 0H5 conformation, was exceptionally low, suggesting that reduction of the 4,6-diacetate having the β- d -threo configuration did not occur from the stable 0H5 conformation, but from

  摘要制备了具有构象柔性的标题化合物，并用硼氢化氘钠还原。氘代离子仅从异头甲氧基的相反侧进攻。然而，采用0H5构象的相应4,6-O-亚苄基-β-d-苏--2-庚吡喃糖苷衍生物的类似还原反应的立体选择性极低，这表明4,6-二乙酸酯的还原反应具有β-d-苏氨酸构型不是由稳定的0H5构象产生的，而是由不稳定的（（5 H 0）构象）产生的。
• Michael reactions on conformationally flexible methyl 3-C-nitro-hex-2-enopyranoside derivatives
  作者：Tohru Sakakibara、Kiohisa Tokuda、Tsutomu Hayakawa、Akinori Seta

  DOI：10.1016/s0008-6215(00)00075-6

  日期：2000.8

  Dimethyl malonate and dibenzoylmethane attacked the C-2 position of the title 3-nitro-2-enopyranosides from the side opposite the anomeric methoxyl group to afford the 3-enopyranosides (S(N)2' products). In the case of 2,4-pentanedione and ethyl acetoacetate, further intramolecular cyclization occurred to yield dihydropyran derivatives. (C) 2000 Elsevier Science Ltd. All rights reserved.