(1R,2S,4'S)-2-<<(tert-Butyldiphenylsilyl)oxy>methyl>-1-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropane | 153861-48-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S,4'S)-2-<<(tert-Butyldiphenylsilyl)oxy>methyl>-1-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropane
• 英文别名: (1S,2R,4'S)-1-<(tert-Butyldiphenylsilyloxy)methyl>-2-(2,2-dimethyl-1,3-dioxolan-4-yl)cyclopropane；(1R,2S,4'S)-2-[(tert-Butyldiphenylsilyloxy)methyl]-1-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropane；tert-butyl[(1S,2R)-2-((S)-2,2-dimethyl[1,3]dioxolan-4-yl)cyclopropylmethyl]diphenylsilane；(1R,2S,4'S)-2-{[(tert-Butyldiphenylsilyl)oxy]methyl}-1-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropane；tert-butyl-[[(1S,2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclopropyl]methoxy]-diphenylsilane
• CAS: 153861-48-4
• 化学式: C₂₅H₃₄O₃Si
• 分子量: 410.629
• InChiKey: YLFIHWKTVLRBOX-UEVCKROQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2S,4'S)-2-<<(tert-Butyldiphenylsilyl)oxy>methyl>-1-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropane 在 N-甲基吗啉 、 potassium permanganate 、 18-冠醚-6 、 potassium hydrogen orthophosphate buffer 、 四丁基氟化铵 、 水 、 四氯化钛 、 sodium hydride 、 高碘酸 、 二乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 叔丁醇 、 苯 为溶剂， 反应 17.41h， 生成 (4R)-2-[(1'R,2'S)-1',2'-Methano-3'-hydroxypropyl]-4-farnesyloxomethyl-4,5-dihydrothiazole
  参考文献：
  名称：

  Synthesis of analogues of the marine anti-tumour agent curacin A

  摘要：

  实现了(4R)-2-[(1′R,2′S)-1′,2′-甲桥-3′-(叔丁基二苯基硅氧基)丙基]-4-羟甲基-4,5-二氢噻唑的简易多克合成，该化合物已被用于生产一系列抗有丝分裂剂仓霉素 A 的类似物。

  DOI：

  10.1039/a904378k
• 作为产物：
  描述：

  (2Z)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-ol 在 4-二甲氨基吡啶 、 diethylzinc 、 三乙胺 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 生成 (1R,2S,4'S)-2-<<(tert-Butyldiphenylsilyl)oxy>methyl>-1-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropane
  参考文献：
  名称：

  Synthesis of analogues of the marine anti-tumour agent curacin A

  摘要：

  实现了(4R)-2-[(1′R,2′S)-1′,2′-甲桥-3′-(叔丁基二苯基硅氧基)丙基]-4-羟甲基-4,5-二氢噻唑的简易多克合成，该化合物已被用于生产一系列抗有丝分裂剂仓霉素 A 的类似物。

  DOI：

  10.1039/a904378k

文献信息

• The synthesis of one enantiomer of the α-methyl-trans-cyclopropane unit of mycolic acids
  作者：Juma'a R. Al-Dulayymi、Mark S. Baird、Hayder Mohammed、Evan Roberts、William Clegg

  DOI：10.1016/j.tet.2006.03.007

  日期：2006.5

  We report the synthesis of a single enantiomer of an α-methyl-trans-cyclopropane unit present in a number of mycolic acids and its incorporation into a reported 1,2-dialkylcyclopropane meromycolate that contains one cis-1,2-dialkylcyclopropane and one α-methyl-trans-1,2-dialkylcyclopropane.

  我们报道了存在于许多霉菌酸中的α-甲基-反式-环丙烷单元的单个对映体的合成，并将其并入已报道的1,2-二烷基环丙烷巯基甲酸酯，该化合物包含一个顺式-1,2-二烷基环丙烷和一个α -甲基-反--1，2-二烷基环丙烷。
• Design and synthesis of 2′-hydroxyethylcyclopropyl carbocyclic nucleosides
  作者：Te-Fang Yang、Hongbum Kim、Lakshmi P. Kotra、Chung K. Chut

  DOI：10.1016/s0040-4039(96)02060-6

  日期：1996.12

  The enantiomeric synthesis of β-D-cyclopropyl carbocyclic nucleosides was achieved via the key intermediate 5. Thymine and uracil derivatives 7 and 9 were obtained by oxidation, Curtius rearrangement and the standard construction method of pyrimidines. The cytosine derivative 10 was prepared from 9via the 4-triazole intermediate.

  β-D-环丙基碳环核苷的对映体合成是通过关键中间体5实现的。胸腺嘧啶和尿嘧啶衍生物7和9是通过氧化，Curtius重排和嘧啶的标准构建方法而获得的。经由4-三唑中间体由9制备胞嘧啶衍生物10。
• Asymmetric Synthesis of (1'S,2'R)-Cyclopropyl Carbocyclic Nucleosides
  作者：Yufen Zhao、Tefang Yang、Migyoung Lee、Doowon Lee、M. Gary Newton、Chung K. Chu

  DOI：10.1021/jo00121a047

  日期：1995.8

  Enantiomeric synthesis of cyclopropyl carbocyclic nucleosides has been accomplished. The key intermediates 7 and 9 were synthesized from D-glyceraldehyde acetonide 1, which was converted to the alpha,beta-unsaturated ester 2 and then reduced to give allylic alcohol 3a. Stereoselective construction of the cyclopropyl ring of 3a and 3b followed by oxidation gave acid 5, which was treated under Curtius rearrangement conditions to obtain the urea intermediate 7. The urea intermediate was utilized to prepare uracil 14, thymine 15, and cytosine 18 nucleosides. The purine derivatives were prepared from cyclopropylamine 9 by condensation with 4,6-dichloro-5-form-amidopyrimidine or 4,6-dichloro-2-aminopyrimidine.
• Synthesis of optically active cis- and trans-1,2-disubstituted cyclopropane derivatives by the Simmons-Smith reaction of allyl alcohol derivatives derived from (R)-2,3-O-isopropylideneglyceraldehyde
  作者：Tsutomu Morikawa、Hirofumi Sasaki、Ryo Hanai、Akira Shibuya、Takeo Taguchi

  DOI：10.1021/jo00080a017

  日期：1994.1

  The Simmons-Smith reactions of Z- and E-allyl alcohol derivatives 6 derived from (R)-2,3-O-isopropylideneglyceraldehyde (5) were used for the synthesis of optically active cis- and trans-1,2 disubstituted cyclopropane derivatives. Reaction of 6 with diethyl zinc and diiodomethane gave cyclopropane derivatives 7 in 84% to quantitative yields with 35 to approximate to 100% des. Identical facial selectivities toward the double bonds, Ire-asi for Z-6 and 1re-2re for E-6, were observed in the cyclopropanations. The diastereoselectivity was dependent on the protecting group on the terminal allylic oxygen (R of 6, TBDPS > MOM > Bn) and on the stereochemistry of the double bond (Z > E). For TBDPS ethers Z- and E-6c, cis- and trans-7c were obtained as single diastereomers respectively. It was clearly demonstrated that the stereoselectivity of the cyclopropanation is controlled by the directing effect of the allylic oxygen (O-1) of the dioxolane ring which coordinates to the reagent. The terminal allylic oxygen (O-2) lowered the diastereoselectivity This reaction was applied to the synthesis of optically active cyclopropane analogs of gamma-aminobutyric acid (GABA) 18, 22, and ent-22.
• Synthesis of analogues of the marine anti-tumour agent curacin A
  作者：Barbara K. D. Martin、John Mann、Olivia A. Sageot

  DOI：10.1039/a904378k

  日期：——

  A concise, multigram synthesis of (4R)-2-[(1′R,2′S)-1′,2′-methano-3′-(tert-butyldiphenylsiloxy)propyl]-4-hydroxymethyl-4,5-dihydrothiazole has been achieved, and this compound has been used for the production of a range of analogues of the anti-mitotic agent curacin A.

  实现了(4R)-2-[(1′R,2′S)-1′,2′-甲桥-3′-(叔丁基二苯基硅氧基)丙基]-4-羟甲基-4,5-二氢噻唑的简易多克合成，该化合物已被用于生产一系列抗有丝分裂剂仓霉素 A 的类似物。