prop-2-enyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside | 67079-55-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: prop-2-enyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
• 英文别名: prop-2-en-1-yl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside；(2R,3S,6S)-2-(hydroxymethyl)-6-prop-2-enoxy-3,6-dihydro-2H-pyran-3-ol
• CAS: 67079-55-4
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: HCQVQZXOQQJSQT-YIZRAAEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  prop-2-enyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 在 咪唑 、 tris(dibenzylideneacetone)dipalladium (0) 、 三乙胺 、 1,4-双(二苯基膦)丁烷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 54.0h， 生成 dimethyl 2-(2-bromoprop-2-enyl)-2-[(2S,3R,6S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-prop-2-enoxy-3,6-dihydro-2H-pyran-3-yl]propanedioate
  参考文献：
  名称：

  碳水化合物模板上钯介导的环化成双环吡喃糖苷的新途径

  摘要：

  描述了一种新的有效途径，通过钯（0）催化的级联环化反应生成双环吡喃糖苷。合适的2，3-不饱和烯丙基糖苷在光滑的Jeffery条件下进行Heck反应，以高收率生产三环衍生物。

  DOI：

  10.1016/0040-4039(95)02096-9
• 作为产物：
  描述：

  prop-2-enyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 prop-2-enyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  碳水化合物模板上钯介导的环化成双环吡喃糖苷的新途径

  摘要：

  描述了一种新的有效途径，通过钯（0）催化的级联环化反应生成双环吡喃糖苷。合适的2，3-不饱和烯丙基糖苷在光滑的Jeffery条件下进行Heck反应，以高收率生产三环衍生物。

  DOI：

  10.1016/0040-4039(95)02096-9

文献信息

• Asymmetric Pauson−Khand Reaction. Cobalt-Mediated Cycloisomerization of 1,6-Enynes in Carbohydrate Templates:  Synthesis of Bis-Heteroannulated Pyranosides
  作者：José Marco-Contelles

  DOI：10.1021/jo961138w

  日期：1996.1.1

  The Pauson-Khand reaction on the carbohydrate derived precursors 1-6 is reported. We have described for the first time the cobalt-mediated cyclization of some O-branched chain 1,6-enynes in carbohydrate templates. The resulting bis-heteroannulated pyranosides 17-22 have been obtained in diastereomerically pure form, in moderate to good yield, and in one, simple synthetic operation. These enantiomerically

  据报道，在碳水化合物衍生的前体1-6上的Pauson-Khand反应。我们首次描述了碳水化合物模板中某些O支链1,6-烯炔的钴介导环化。以非对映体纯的形式，以中等至良好的收率，并且以一种简单的合成操作，获得了所得的双-异环吡喃糖苷17-22。这些对映体纯，稠密官能化的碳环是用于合成复杂天然产物的有吸引力的高级中间体。
• [1,2]- vs [2,3]-Wittig Rearrangement in Carbohydrate Derived Alkenyl Systems
  作者：Ramu Sridhar Perali、Umamaheswara Rao Boddu、Drisya Chittadi Sankar

  DOI：10.1021/acs.orglett.1c00988

  日期：2021.5.21

  A simple and efficient strategy for the regio- and stereoselective synthesis of carbon-branched sugar derivatives is described. The successful implementation of Wittig rearrangement on substrates derived by Ferrier rearrangement of various glycals and 3-O-alkenyl glycals is studied extensively. A highly selective [1,2]- or [2,3]-Wittig rearrangement is revealed that provides a novel class of stereodefined

  描述了一种用于碳支化糖衍生物的区域和立体选择性合成的简单有效策略。广泛研究了在通过各种糖和3- O-烯基糖的费勒重排衍生的底物上成功进行维蒂希重排。揭示了高度选择性的[1,2]-或[2,3] -Wittig重排，其提供了一类新颖的立体定义的3- C-支链糖基和C-糖苷，否则难以获得。
• Palladium-mediated cyclisation on carbohydrate templates A new route to bis-annulated pyranosides
  作者：Jean-Flaubert Nguefack、Véronique Bolitt、Denis Sinou

  DOI：10.1016/0040-4039(95)02096-9

  日期：1996.1

  A new and efficient route to bis-annulated pyranosides by palladium(0)-catalysed cascade cyclisation is described. The appropriate 2,3-unsaturated allylglycosides are subjected to Heck reaction under smooth Jeffery's conditions to produce the tricyclic derivatives in good yields.

  描述了一种新的有效途径，通过钯（0）催化的级联环化反应生成双环吡喃糖苷。合适的2，3-不饱和烯丙基糖苷在光滑的Jeffery条件下进行Heck反应，以高收率生产三环衍生物。
• Konstantinovic; Predojevic; Gojkovic, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 9, p. 802 - 805
  作者：Konstantinovic、Predojevic、Gojkovic、Ratkovic、Dimitrijevic、Mojsilovic

  DOI：——

  日期：——
• Palladium-Mediated Cyclization on Carbohydrate Templates. 2. Synthesis of Enantiopure Tricyclic Compounds
  作者：Jean-Flaubert Nguefack、Véronique Bolitt、Denis Sinou

  DOI：10.1021/jo970817j

  日期：1997.10.1

  The bromo substituted unsaturated carbohydrates 3a-f were prepared from 3,4,6-tri-O-acetyl-D-glucal by Ferrier reaction with the appropriate allylic or homoallylic alcohol, deacetylation followed by monosilylation with TBDMSCl, and then alkylation with BrCH2CBr=CH2. The N- and C-analogues 4a,b were synthesized by palladium alkylation of the intermediate carbonate with TsNHCH2CBr=CH2 and (MeO2C)(2)CHCH2CBr=CH2, respectively. Treatment of the unsaturated carbohydrates 3a, 4a, and 4b with a catalytic amount of Pd(OAc)(2)/PPh3 in CH3CN/H2O, in the presence of Bu4NHSO4 and NEt3, afforded the tricyclic compounds 5, 6, and 7, respectively. Under the same conditions, the analogue tricyclic compounds 8, 9, and 10 were formed starting from 3b-d. In the case of compounds 3e and 3f, the formation of the bicyclic glucal 11 via an already described beta-alkoxyelimination was only observed. Moreover, trapping of the sigma-alkylpalladium intermediate obtained from 3e with an external nucleophile yielded the 2-deoxy carbohydrate 12 and the 2,3-unsaturated sugar 13, using respectively sodium formate and sodium tetraphenylborate.