3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose | 19877-13-5

• 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: 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose
• 英文别名: 5,6-dideoxy-1,2-O-isopropylidene-3-O-benzyl-α-D-xylo-hex-5-enofuranose；3-O-benzyl-5,6-dideoxy-α/β-D-xylo-hex-5-enofuranose；3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-ribo-hexofuran-5-ene；5,6-dideoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-xylohex-5-eno-furanose；O³-benzyl-O¹,O²-isopropylidene-α-D-xylo-5,6-dideoxy-hex-5-enofuranose；O³-Benzyl-O¹,O²-isopropyliden-α-D-xylo-5,6-didesoxy-hex-5-enofuranose；(3aR,5R,6S,6aR)-5-ethenyl-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 19877-13-5
• 化学式: C₁₆H₂₀O₄
• 分子量: 276.332
• InChiKey: NSJZJRZQKBXUTL-LXTVHRRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose 在 盐酸 、 三正丁基氢锡 、 sodium hydride 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 130.25h， 生成 (2R,3R,5S)-3-(benzyloxy)-5-methoxy-2-vinyltetrahydrofuran
  参考文献：
  名称：

  Synthetic routes to 6,8-dioxabicyclo[3.2.1]octyl pheromones from D-glucose derivatives. 2. Synthesis of (+)-exo-brevicomin

  摘要：

  DOI：

  10.1021/jo00345a006
• 作为产物：
  描述：

  3-O-benzyl-1,2-O-isopropylidene-5,6-di-O-mesyl-α-D-glucofuranose 在 sodium iodide 作用下， 以 丁酮 为溶剂， 反应 24.0h， 以100%的产率得到3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose
  参考文献：
  名称：

  Synthetic routes to 6,8-dioxabicyclo[3.2.1]octyl pheromones from D-glucose derivatives. 2. Synthesis of (+)-exo-brevicomin

  摘要：

  DOI：

  10.1021/jo00345a006

文献信息

• Reaction of chlorosulphonyl isocyanate with unsaturated sugars
  作者：R. H. Hall、A. Jordaan、G. J. Lourens

  DOI：10.1039/p19730000038

  日期：——

  Treatment of hex-2-enopyranosides with chlorosulphonyl isocyanate gives 3-alkoxycarbonylamino-3-deoxyglycals. 1,2-O-Isopropylidene groups in sugars are removed by the reagent and 1,2-carbonates are formed.

  用异氰酸氯磺酰基酯处理己-2-烯吡喃糖苷，得到3-烷氧基羰基氨基-3-脱氧糖醛。1,2- Ó在糖亚异丙基团通过在试剂中去除，并形成1,2-碳酸酯。
• Catalytic asymmetric dihydroxylation of olefins using polysulfone-based novel microencapsulated osmium tetroxide
  作者：S. Malla Reddy、M. Srinivasulu、Y. Venkat Reddy、M. Narasimhulu、Y. Venkateswarlu

  DOI：10.1016/j.tetlet.2006.05.138

  日期：2006.7

  polymer-supported osmium catalyst has been developed. The catalyst was prepared from commercially available polysulfone, based on a microencapsulation technique and was employed in the asymmetric dihydroxylation of various olefins using (DHQD)2PHAL as the chiral ligand and NMO as the co-oxidant in H2O–acetone–CH3CN (1:1:1). The catalyst was recovered by simple filtration and was reused to obtain excellent yields with

  已经开发了基于聚砜的新型聚合物负载的catalyst催化剂。该催化剂是基于微囊化技术，由市售的聚砜制备的，并用于（DHQD）2 PHAL作为手性配体，NMO作为H 2 O-丙酮-CH 3中的助氧化剂，用于各种烯烃的不对称二羟基化反应。CN（1：1：1）。通过简单的过滤回收催化剂，并重复使用以获得高达五倍的良好对映选择性的优异产率。
• First Total Synthesis of the Proposed Structure of Pandangolide 1
  作者：Krishanu Show、Rajesh G. Gonnade、Pradeep Kumar

  DOI：10.1002/ejoc.201800675

  日期：2018.7.6

  The first total synthesis of the proposed structure of pandangolide 1 is reported. The structure of the target molecule was confirmed unambiguously by single‐crystal X‐ray analysis, but the optical rotation and NMR spectroscopic data of the synthetic pandangolide 1 were found to be inconsistent with the natural product.

  报道了潘丹高利德1拟议结构的第一个全合成。通过单晶X射线分析明确确定了目标分子的结构，但发现合成的潘丹高利德1的旋光度和NMR光谱数据与天然产物不一致。
• Synthesis of C1- and C8a-epimers of (+)-castanospermine from d-glucose derived γ,δ-epoxyazide: intramolecular 5-endo epoxide opening approach
  作者：Navnath B. Kalamkar、Vedavati G. Puranik、Dilip D. Dhavale

  DOI：10.1016/j.tet.2011.02.030

  日期：2011.4

  A concise synthesis of two diastereomers of (+)-castanospermine namely 1- and 8a-epi-castanospermine 1b and 1c, respectively, is reported from d-glucose. The methodology involves stereoselective cross metathesis of d-glucose derived alkene 2 with 4-bromo-1-butene followed by azide displacement and m-CPBA oxidation to afford diastereomeric γ,δ-epoxyazides 5a/5b. The Staudinger reaction of epoxyazide

  从d-葡萄糖报道了两个（+）- castanospermine的非对映异构体的简明合成，分别是1-和8a- epi- castanospermine 1b和1c。该方法包括将d-葡萄糖衍生的烯烃2与4-溴-1-丁烯进行立体选择性交叉复分解，然后进行叠氮化物置换和m- CPBA氧化，得到非对映异构体γ，δ-环氧叠氮化物5a / 5b。环氧叠氮化物5a的Staudinger反应，然后与氯甲酸苄酯（CbzCl）反应，出乎意料地提供了1,3-恶二嗪-2-酮衍生物7其立体化学是通过单晶X射线建立的。这有助于在环氧化反应中分配立体化学。然后通过转移氢化进行5a / 5b还原，以提供γ，δ-环氧胺，同时进行分子内5-内-tet环化反应，得到带有糖骨架的羟基吡咯烷环骨架-粟精胺类似物1b / 1c的前体。
• A flexible synthesis of cyclopentitol derivatives based on ring-closing metathesis of carbohydrate-derived 1,6-dienes
  作者：Huib Ovaa、Bas Lastdrager、Jeroen D. C. Codée、Gijs A. van der Marel、Herman S. Overkleeft、Jacques H. van Boom

  DOI：10.1039/b207509a

  日期：——

  Four partially protected stereoisomeric cyclopentenetriols 5, 10, 15 and 21 have been prepared by ring-closing metathesis of carbohydrate-derived 1,6-dienes. The presence of a differentiated allylic alcohol in the cyclopentenetriols allows a variety of synthetic transformations, underlining the synthetic use of the prepared cyclopentenetriol derivatives as chiral building blocks.

  四个部分保护的立体异构环戊烯三醇5、10、15和21已通过碳水化合物衍生的1,6-二烯的环闭合易位反应制备。环戊烯三醇中存在一个区分的烯丙醇，使其能够进行多种合成转化，强调了制备的环戊烯三醇衍生物作为手性构建模块的合成应用。