(2R/S,3R)-3-(Benzyloxy)tetrahydro-4,4-dimethylfuran-2-ol | 277317-84-7

• 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: (2R/S,3R)-3-(Benzyloxy)tetrahydro-4,4-dimethylfuran-2-ol
• 英文别名: (3R)-3-(benzyloxy)-4,4-dimethyltetrahydrofuran-2-ol；(3R)-3-benzyloxy-4,4-dimethyl-tetrahydro-furan-2-ol；(R)-3-benzyloxy-4,4-dimethyl-tetrahydro-furan-2-ol；(3R)-3-benzyloxy-4,4-dimethyltetrahydrofuran-2-ol；(R)-3-benzyloxy-4,4-dimethyl-tetrahydrofuran-2-ol；(R)-3-benzyloxy-4,4-dimethyl-dihdyro-furan-2-ol；(3R)-4,4-dimethyl-3-phenylmethoxyoxolan-2-ol
• CAS: 277317-84-7
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: RBDRWTINHWPJHS-PXYINDEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R/S,3R)-3-(Benzyloxy)tetrahydro-4,4-dimethylfuran-2-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 (3R,4R,5R)-6,6-dimethyl-5-phenylmethoxyoxepane-3,4-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：

  D-(-)-泛酰内酯 在 二异丁基氢化铝 、 silver(l) oxide 作用下， 以 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (2R/S,3R)-3-(Benzyloxy)tetrahydro-4,4-dimethylfuran-2-ol
  参考文献：
  名称：

  泛酸和磷酸泛酸的模块合成。

  摘要：

  [结构：见正文] D-泛素和D-磷酸泛素是辅酶A的前体，已分别通过三个模块（M1-M3）的线性序列分别以9个步骤和10个步骤合成。这些途径提供了获得辅酶A类似物的途径，所述辅酶A包含修饰的胱胺，β-丙氨酸和泛酸残基。使用肽合成的常规方法将所有三个模块连接在一起。手性组分M3衍生自D-泛内酯。

  DOI：

  10.1021/ol048853+

文献信息

• Synthesis of the C(1)C(16) fragment of bryostatins
  作者：Matthew O'Brien、Nicholas H Taylor、Eric J Thomas

  DOI：10.1016/s0040-4039(02)01054-7

  日期：2002.7

  A synthesis of the C(1)C(16) fragment 43 of the bryostatins is reported which features a stereoselective equivalent of an ‘ene’ reaction between the allylsilane 35 and the alkynone 33 and the stereoselective conjugate addition–cyclisation of the dienyl ketone 36 to give the acetal 39 after acetalisation.

  报道了溴抑他汀的C（1）C（16）片段43的合成，该合成具有烯丙基硅烷35和炔酮33之间的“烯”反应的立体选择性当量，以及二烯基酮的立体选择性共轭加成环化36在缩醛化后得到缩醛39。
• Lewis Acid Catalyzed Ring-Opening Reactions of Sugar-Derived Semicyclic N,O-Acetals
  作者：Masaharu Sugiura、Hiroyuki Hagio、Shu Kobayashi

  DOI：10.1002/1522-2675(200211)85:11<3678::aid-hlca3678>3.0.co;2-0

  日期：2002.11

  efficiently synthesized from regular acetyl or methyl glycosides (glucopyranoside, ribofuranoside, arabinofuranoside, and 2-deoxyribofuranoside) and a carbamate by treatment of trimethylsilyl trifluoromethanesulfonate and 4 A molecular sieves. It was found that these N-glycosides underwent Lewis acid catalyzed ring-opening reactions with silylated nucleophiles to give ring-opened amino alcohols with good-to-high

  N-(烷氧基羰基)-N-糖苷(聚氧半环N,O-缩醛) 由常规乙酰基或甲基糖苷(吡喃葡萄糖苷、呋喃核糖苷、阿拉伯呋喃糖苷和2-脱氧呋喃核糖苷) 和氨基甲酸酯通过三甲基甲硅烷基三氟甲磺酸酯和4 A 处理有效合成分子筛。发现这些N-糖苷与硅烷化亲核试剂发生路易斯酸催化的开环反应，得到具有良好至高非对映选择性的开环氨基醇。揭示了反应性顺序，2-脱氧呋喃糖苷 > 阿拉伯呋喃糖苷 > 呋喃糖苷 > 吡喃葡萄糖苷。还用硅烷或氢化二异丁基铝研究了开环还原。发现合适的还原剂取决于所使用的 N-糖苷。糖苷酶抑制剂，（2S，3R，
• Total Synthesis of Bryostatin 8 Using an Organosilane-Based Strategy
  作者：Yuebao Zhang、Qianyou Guo、Xianwei Sun、Ji Lu、Yanjun Cao、Qiang Pu、Zhiwen Chu、Lu Gao、Zhenlei Song

  DOI：10.1002/anie.201711452

  日期：2018.1.22

  Convergent total synthesis of bryostatin 8 has been accomplished by an organosilane‐based strategy. The C ring is constructed stereoselectively through a geminal bis(silane)‐based [1,5]‐Brook rearrangement, and the B ring through geminal bis(silane)‐based Prins cyclization, thus efficiently joining the northern and southern parts of the molecule.

  bryostatin 8的聚合全合成已通过基于有机硅烷的策略完成。C环通过基于双（硅烷）的双[1,5] -Brook重排立体选择，B环通过基于双（硅烷）的Prins环化而立体构建，从而有效地连接了分子的北部和南部。
• Samarium(II)-mediated 4-exo-trig cyclisations of unsaturated aldehydes. A stereoselective approach to functionalised cyclobutanols
  作者：Derek Johnston、Catherine F. McCusker、Kenneth Muir、David J. Procter

  DOI：10.1039/a909549g

  日期：——

  γ,δ-Unsaturated aldehydes having a fully substituted centre in either the α- or β-positions, have been prepared from substituted γ-butyrolactones and undergo efficient 4-exo-trig cyclisation on treatment with samarium(II) iodide to give functionalised cyclobutanols. In all cases cyclisation occurs with complete diastereocontrol to give anti-cyclobutanol products. The stereochemistry of the products has been confirmed by NOE and X-ray crystallographic studies. In the cyclisation of substrates having a third substituent on the double bond, α- to the ester, significant control is achieved at the third newly formed stereocentre lying outside the ring. The origin of the stereoselectivity at this third centre and its marked dependence on cosolvent are discussed.

  γ,δ-不饱和醛具有完全取代的中心，无论是在α-还是β-位置，均是通过取代的γ-丁内酯制备的，并在处理时与锶(II)碘化物发生高效的4-exo-trig环化反应，生成功能化的环丁醇。在所有情况下，环化反应都以完全的非对映选择性进行，生成反式环丁醇产物。产物的立体化学已通过NOE和X射线晶体学研究得到确认。在具有双键上第三个取代基的底物的环化反应中，位于环外的新形成的第三个立体中心实现了显著的控制。讨论了该第三个中心的立体选择性的来源及其对共溶剂的显著依赖性。
• NOVEL TRICYCLIC COMPOUNDS AND PREPARATION THEREOF
  申请人：COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH

  公开号：US20160362371A1

  公开（公告）日：2016-12-15

  The present invention provides novel tricyclic compound of Formula I or its stereoisomer or ester or pharmaceutically acceptable salts and preparation thereof useful for treatment of cancer.

  本发明提供了一种新颖的三环化合物，其化学式为I，或其立体异构体、酯或药学上可接受的盐及其制备方法，用于治疗癌症。