2,5-dideoxy-5-iodo-D-ribonic acid-γ-lactone | 82166-98-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 2,5-dideoxy-5-iodo-D-ribonic acid-γ-lactone
• 英文别名: (4S,5S)-4-hydroxy-5-(iodomethyl)oxolan-2-one
• CAS: 82166-98-1
• 化学式: C₅H₇IO₃
• 分子量: 242.013
• InChiKey: QJIYRZUTCSEHHG-IUYQGCFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-dideoxy-5-iodo-D-ribonic acid-γ-lactone 在 咪唑 、 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 生成 2,5-dideoxy-5-iodo-3-O-(tert-butyldimethylsilyl)-D-ribose
  参考文献：
  名称：

  Studies on the diastereoselectivity of samarium(II) iodide mediated reductive carbocyclizations of ω-iodo-α,β-unsaturated esters prepared from 2-deoxy-d-ribose

  摘要：

  The title compounds were reduced with SmI2 or Bu3SnH to give carbocyclic compounds in good yield. The stereoselectivity of the SmI2 reductive carbocyclizations varies with the reaction conditions, the double bond geometry and with the identity of the hydroxyl protecting groups. Keywords: Alkenyl halides, carbohydrates, cyclisation, samarium and compounds.

  DOI：

  10.1016/s0040-4039(98)01552-4
• 作为产物：
  描述：

  D-(+)-核糖酸-1,4-内酯 在 吡啶 、 三氟乙酸 、 sodium iodide 、 lithium bromide 作用下， 以 丙酮 为溶剂， 反应 6.0h， 生成 2,5-dideoxy-5-iodo-D-ribonic acid-γ-lactone
  参考文献：
  名称：

  有关美登木素生物碱合成的研究。

  摘要：

  已经研究了两种双-双美登木素生物碱的C 1 -C 5部分合成的方法，一方面从（S）-（-）-苹果酸开始，另一方面从D-（+）-核糖内酯开始。

  DOI：

  10.1016/s0040-4039(00)86913-0

文献信息

• New Synthesis of All Four Isomers of 3-Hydroxy-4-methyl-.gamma.-butyrolactone by Stereoselective Intramolecular Lactonization. Application to Asymmetric Synthesis of Biologically Active Compounds
  作者：Hiroki Takahata、Yasuhiro Uchida、Takefumi Momose

  DOI：10.1021/jo00103a008

  日期：1994.12

  A new synthesis of all four isomeric 3-hydroxy-4-methyl-gamma-butyrolactones (11, ent-11, 12, ent-12) has been performed. The former two were prepared via stereoselective iodolactonization, which favors the cis-3,4-disubstituted system (16a and ent-16a), of N-benzyl-N-methyl-3-hydroxy-4-pentenamides (R)- and (S)-13, readily available by resolution of the racemate by lipase-mediated transesterification; and the latter two were prepared via stereoselective oxylactonization, which favors the trans-3,4-disubstituted system [(3R,4S)-20a and ent-(3R,4S)-20a], of O-TBDMS-protected N-benzyl-N-methyl-3-hydroxy-4-pentenamides (R)- and (S)-14. Butyrolactones 11 and 12 have been readily transformed into biologically active compounds [(-)-blastmycinolactol (27), (-)-NFX-2 (2), (-)-NFX-4 (3), lipid metabolites 9 and 10, and the sex pheromone (-)-(2S,3S)-2,3-octanediol (30)].
• Studies on the diastereoselectivity of samarium(II) iodide mediated reductive carbocyclizations of ω-iodo-α,β-unsaturated esters prepared from 2-deoxy-d-ribose
  作者：Sharon M. Bennett、Raphinos Kouya Biboutou、Bita Samim Firouz Salari

  DOI：10.1016/s0040-4039(98)01552-4

  日期：1998.9

  The title compounds were reduced with SmI2 or Bu3SnH to give carbocyclic compounds in good yield. The stereoselectivity of the SmI2 reductive carbocyclizations varies with the reaction conditions, the double bond geometry and with the identity of the hydroxyl protecting groups. Keywords: Alkenyl halides, carbohydrates, cyclisation, samarium and compounds.
• Functionalized chiral γ-butyrolactones as C5 building units: a straightforward formal synthesis of (+)- exo- and (+)-endo-brevicomines
  作者：Hiroki Takahata、Mami Kusunoki、Yuka Takeda、Takefumi Momose

  DOI：10.1016/0957-4166(96)00252-2

  日期：1996.7

  A straightforward formal synthesis of the insect pheromones (+)-exo-brevicomin 3 and (+)-endo-brevicomin 4 starting from homochiral functionalized gamma-butyrolactones 1 and 2 as C-5 building units is presented. Copyright (C) 1996 Published by Elsevier Science Ltd
• Studies related to the synthesis of maytansinoids.
  作者：Derek H.R. Barton、Michel Bénéchie、Françoise Khuong-Huu、Pierre Potier、Victor Reyna-Pinedo

  DOI：10.1016/s0040-4039(00)86913-0

  日期：1982.1

  Two approaches to the partial synthesis of C1–C5 of a bis-nor maytansinoid have been investigated starting on the one hand with (S)-(−)-malic acid and on the other, with D-(+)-ribonolactone.

  已经研究了两种双-双美登木素生物碱的C 1 -C 5部分合成的方法，一方面从（S）-（-）-苹果酸开始，另一方面从D-（+）-核糖内酯开始。
• Influence of Various Promoters on the Diastereoselectivity of Samarium(II) Iodide Mediated Reductive Carbocyclizations of ω-Iodo-α,β-unsaturated Esters Prepared from 2-Deoxy-d-ribose
  作者：Bita Samim Firouz Salari、Raphinos Kouya Biboutou、Sharon M Bennett

  DOI：10.1016/s0040-4020(00)00583-4

  日期：2000.8

  omega-Iodo-alpha,beta-unsaturated esters were reduced with SmI2 or Bu3SnH under different conditions to give carbocyclic compounds in good yield. The stereoselectivity of the SmI2 cyclizations varies with the choice of promoter, the reaction temperature, the identity of the hydroxyl protecting groups and the geometry of the double bond. (C) 2000 Elsevier Science Ltd. All rights reserved.