(1R)-(+)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-ol | 97204-83-6

• 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: (1R)-(+)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-ol
• 英文别名: (1R)-1-[(4R,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenylmethoxyethanol
• CAS: 97204-83-6
• 化学式: C₁₆H₂₂O₄
• 分子量: 278.348
• InChiKey: YZSTXURBHKNUCX-QLFBSQMISA-N

物化性质

• 沸点：
  395.5±37.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R)-(+)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-ol 在 四氧化锇 、 Grubbs catalyst first generation 、 N-甲基吲哚酮 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 水 、 苯 为溶剂， 生成 (3aR,4R,7R,8R,8aS)-4-Benzyloxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]oxepine-7,8-diol
  参考文献：
  名称：

  A ring closing metathesis-osmylation approach to oxygenated oxepanes as carbohydrate surrogates

  摘要：

  A ring closing metathesis (RCM)-osmylation sequence has been developed for the formation of highly oxygenated cyclic ethers from the corresponding acyclic dienes. A systematic examination of various substrates in this reaction revealed that the process is general in scope and is insensitive to the number of alkoxy substituents present. Subsequent osmylation of the metathesis product proceeds with excellent diastereoselectivity to furnish highly oxygenated oxepanes. These oxepanes represent one-carbon homologated carbohydrates. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01881-x
• 作为产物：
  描述：

  2,3-O-异亚丙基-D-核糖酸 gamma-内酯 在 正丁基锂 、 二异丁基氢化铝 、 silver(l) oxide 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 (1R)-(+)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(benzyloxy)ethan-1-ol
  参考文献：
  名称：

  6-O-苄基-1,2-二-脱氧-3,4-O-异亚丙基-d-核糖-己糖-1-烯醇的亲电介导环化为2,5-脱水-6-O-苄基的衍生物-3,4-O-异亚丙基-d-己糖醇

  摘要：

  摘要亲电试剂（溴，碘，乙酸汞，三氟乙酸汞，苯基硒基氯）介导的6-O-苄基-1,2-二脱氧-3,4- O-异亚丙基-d-核糖-己基-1-烯醇的环化（ 2）仅导致2，5-脱水-6-O-苄基-3,4-O-异亚丙基-d-α-己糖醇的1-取代的衍生物（3）。讨论了烯烃2的合成及其环化成己糖醇3衍生物的机理和立体化学方面。

  DOI：

  10.1016/0008-6215(85)85151-x

文献信息

• Electrophile-mediated cyclizations of 6-O-benzyl-1,2-di- deoxy-3,4-O-isopropylidene-d-ribo-hex-1-enitol to derivatives of 2,5-anhydro-6-O-benzyl-3,4-O-isopropylidene-d-altro-hexitol
  作者：Fillmore Freeman、Kirk D. Robarge

  DOI：10.1016/0008-6215(85)85151-x

  日期：1985.3

  mercuric acetate, mercuric trifluoroacetate, phenylselenyl chloride)-mediated cyclization of 6- O -benzyl-1,2-dideoxy-3,4- O - isopropylidene- d - ribo -hex-1-enitol ( 2 ) led exclusively to 1-substituted derivatives of 2,5-anhydro-6- O -benzyl-3,4- O -isopropylidene- d - altro -hexitol ( 3 ). The synthesis of alkene 2 , together with mechanistic and stereochemical aspects of its cyclization to derivatives

  摘要亲电试剂（溴，碘，乙酸汞，三氟乙酸汞，苯基硒基氯）介导的6-O-苄基-1,2-二脱氧-3,4- O-异亚丙基-d-核糖-己基-1-烯醇的环化（ 2）仅导致2，5-脱水-6-O-苄基-3,4-O-异亚丙基-d-α-己糖醇的1-取代的衍生物（3）。讨论了烯烃2的合成及其环化成己糖醇3衍生物的机理和立体化学方面。
• Preparative Synthesis of the Key Intermediate, (4<i>R</i>,5<i>R</i>)-3-Benzyloxymethyl-4,5-isopropylidenedioxycyclopent-2-enone for Carbocyclic Nucleosides
  作者：Hyung Ryong Moon、Won Jun Choi、Hea Ok Kim、Lak Shin Jeong

  DOI：10.1246/cl.2004.506

  日期：2004.5

  (4R,5R)-3-Benzyloxymethyl-4,5-isopropylidenedioxycyclopent-2-enone (1), a versatile intermediate for the synthesis of carbocyclic nucleosides was synthesized from D-ribose in 10 steps and 26% overa...

  (4R,5R)-3-Benzyloxymethyl-4,5-isopropylidenedioxycyclopent-2-enone (1) 是一种用于合成碳环核苷的通用中间体，由 D-核糖分 10 步合成，合成率 26%。
• A simple and efficient PdCl2 mediated conversion of γ,δ-olefinic alcohols into C-glycosides
  作者：GVM Sharma、A.Subash Chander、K Krishnudu、Palakodety Radha Krishna

  DOI：10.1016/s0040-4039(97)10432-4

  日期：1997.12

  An efficient and mild intramolecular oxidative nucleophilic cyclisation protocol has been developed for the conversion of γ, δ-olefinic alcohols into the hemiketals, which in turn on deoxygenation led to the very important C-glycoside class of compounds.

  已经开发出一种有效且温和的分子内氧化亲核环化方案，用于将γ，δ-烯烃醇转化为半缩酮，这反过来又导致脱氧，从而导致了非常重要的C-糖苷类化合物。
• Preparative and Stereoselective Synthesis of the Versatile Intermediate for Carbocyclic Nucleosides:  Effects of the Bulky Protecting Groups to Enforce Facial Selectivity
  作者：Won Jun Choi、Hyung Ryong Moon、Hea Ok Kim、Byul Nae Yoo、Jeong A Lee、Dae Hong Shin、Lak Shin Jeong

  DOI：10.1021/jo0356762

  日期：2004.4.1

  The preparative and stereoselective synthesis (45-50% overall yields) of the target compound 17 has been accomplished from D-ribose. The bulky protecting groups such as TBDPS and Trityl enforced the facial selectivity during Grignard reaction to give the tertiary beta-allylic alcohol 16 as the sole product, which was oxidatively rearranged to the key molecule 17 in excellent yield.
• STEREOSELECTIVE SYNTHESIS OF 3-HYDROXYMETHYL-D-CYCLOPENTENONE, THE VERSATILE INTERMEDIATE FOR THE SYNTHESIS OF CARBOCYCLIC NUCLEOSIDES
  作者：Won Jun Choi、Hyung Ryong Moon、Hea Ok Kim、Young Mi Ko、Hye Jin Kim、Jeong A. Lee、Kang Man Lee、Mi Kyung Yun、Dae Hong Shin、Moon Woo Chun、Yhun Y. Sheen、Kilhyoun Kim、Lak Shin Jeong

  DOI：10.1081/ncn-200061832

  日期：2005.4.1

  The preparative and stereoselective synthesis (45 - 50% overall yields, >50 g scale) of the key carbasugars 7a-d was achieved from D-ribose via stereoselective Grignard reaction and oxidative rearrangement as key reactions.