5-(benzylamino)-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose | 148703-38-2

• 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: 5-(benzylamino)-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose
• 英文别名: (3aR,5R,6S,6aR)-5-[(benzylamino)methyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• CAS: 148703-38-2
• 化学式: C₁₅H₂₁NO₄
• 分子量: 279.336
• InChiKey: WBTOJPQYWKDVTO-XJFOESAGSA-N

物化性质

• 沸点：
  417.8±40.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  60
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(benzylamino)-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose 在 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以44%的产率得到(4aR,5aR,8aR,8bS)-3-Benzyl-2-chloro-7,7-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-e][1,3,2]oxazaphosphinine 2-oxide
  参考文献：
  名称：

  Preparation of Novel Cyclophosphamides Derivatives of Sugars

  摘要：

  Novel cyclophosphamide derivatives bearing a sugar structure were prepared by the treatment of the amino sugars from D-glucose and D-xylose with bis-(2-chloroethyl)aminophosphoric dichloride as well as with phosphoryl chloride and nucleophiles.

  DOI：

  10.3987/com-92-6211
• 作为产物：
  描述：

  3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.0h， 生成 5-(benzylamino)-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose
  参考文献：
  名称：

  [EN] NOVEL DERIVATIVES OF ACYL CYANOPYRROLIDINES
  [FR] NOUVEAUX DÉRIVÉS D'ACYLE CYANOPYRROLIDINES

  摘要：

  公开号：

  WO2009116067A3

文献信息

• Rh-Catalyzed Asymmetric Hydroaminomethylation of α-Substituted Acrylamides: Application in the Synthesis of RWAY
  作者：Roger Miró、Anton Cunillera、Jèssica Margalef、Domke Lutz、Armin Börner、Oscar Pamiès、Montserrat Diéguez、Cyril Godard

  DOI：10.1021/acs.orglett.0c03433

  日期：2020.11.20

  hydroformylation and hydroaminomethylation of α-substituted acrylamides is described using 1,3-phosphite-phosphoramidite ligands based on a sugar backbone. A broad scope of chiral aldehydes and amines were afforded in high yields and excellent enantioselectivities (up to 99%). Furthermore, the synthetic potential of this method is demonstrated by the single-step synthesis of the brain imaging molecule RWAY.

  使用基于糖主链的1，3-亚磷酸酯-亚磷酰胺配体描述了成功的铑催化α-取代的丙烯酰胺的不对称加氢甲酰化和氢氨基甲基化。以高收率和优异的对映选择性（高达99％）提供了广泛的手性醛和胺。此外，通过脑成像分子RWAY的一步合成证明了该方法的合成潜力。
• Catalytic enantioselective reaction. Part 9. 1,2-O-Isopropylidene-5-deoxy-5-N,N-dialkyl (or -N-monoalkyl)amino-α-<scp>D</scp>-xylofuranose derivatives as highly effective chiral catalysts for enantioselective addition of diethylzinc to aliphatic and aromatic aldehydes
  作者：Byung Tae Cho、Namdu Kim

  DOI：10.1039/p19960002901

  日期：——

  (or-N-monoalkyl)amino-α-D-xylofuranose derivatives have been prepared form D-xylose and their enantioselectivities as chiral catalysts for the addition of diethylzinc to aldehydes have been examined. Or the chiral catalysts examined, 5-deoxy-1,2-O-isopropylidene-5-morpholino-α-D-xylofuranose provides high enantioselectivity for aromatic and relatively hindered aliphatic aldehydes, and 5-deoxy-5-hexaydroazepinyl-1

  一系列新的1,2- ö异亚丙基-5-脱氧-5- Ñ，Ñ二烷基（或- Ñ -monoalkyl）氨基α- d -xylofuranose衍生物已被制备的形式d木糖以及它们的对映选择性手性已经研究了用于将二乙基锌加成到醛中的催化剂。或所研究的手性催化剂5-脱氧-1,2- O-异亚丙基-5-吗啉代-α- D-木呋喃糖为芳香族和相对受阻的脂族醛和5-脱氧-5-六氮杂pin啶基-1,2提供了高对映选择性- ö异亚丙基α- d -xylofuranose为受阻的脂族醛高度有效的。
• Novel chiral xylofuranose-based phosphinooxathiane and phosphinooxazinane ligands for palladium-catalyzed asymmetric tandem allylic allylation
  作者：Hiroto Nakano、Jun-ichi Yokoyama、Reiko Fujita、Hiroshi Hongo

  DOI：10.1016/s0040-4039(02)01830-0

  日期：2002.10

  Novel chiral xylofuranose-based phosphinooxathiane and phosphinooxazinane ligands have been synthesized and found to be effective ligands for palladium-catalyzed asymmetric tandem allylic allylations of 1,4-diacetoxy-cis-2-butene with 2-(benzylamino)ethanol or 1,2-bis[benzylamino]ethane to give chiral 4-benzyl-2-vinylmorpholine (94% ee) or 1,4-dibenzyl-2-vinylpiperazine (70% ee).

  已经合成了新颖的基于手性木呋喃糖的膦氧杂氧杂环丁烷和膦氧恶嗪烷配体，并且发现它们是钯催化的1,4-二乙酰氧基-顺式-2-丁烯与2-（苄基氨基）乙醇或1,2-的钯催化的不对称串联烯丙基烯丙基化的有效配体。双[苄氨基]乙烷得到手性4-苄基-2-乙烯基吗啉（94％ee）或1,4-二苄基-2-乙烯基哌嗪（70％ee）。
• Sugar Based γ-Amino Alcohol Organocatalyst for Asymmetric Michael Addition of β-Keto Esters with Nitroolefins
  作者：Hiroto Nakano、Divakar Ganesan、Madhu Chennapuram、Zubeda Begum、Chigusa Seki、Yuko Okuyama、Eunsang Kwon、Koji Uwai、Michio Tokiwa、Suguru Tokiwa、Mitsuhiro Takeshita

  DOI：10.3987/com-19-14172

  日期：——

  Division of Sustainable and Environmental Engineering, Graduate School of Engineering, Muroran Institute of Technology, 27-1 Mizumoto-cho, Muroran 050-8585, E-mail: [e-mail] Tohoku Medical and Pharmaceutical University, 4-4-1 Komatsushima, Aoba-Ku, Sendai 981-8558, Japan, E-mail: [e-mail] Research and Analytical Center for Giant Molecules, Graduate School of Sciences

  室兰工业大学工学研究生院可持续与环境工学部，室兰水本町27-1 050-8585，电子邮件：[e-mail] 东北医科大学， 4-4-1 Komatsushima, Aoba-Ku, Sendai 981-8558, Japan, E-mail: [e-mail] 东北大学研究生院大分子研究和分析中心, 6-3 Aoba, Aramaki, Aoba-Ku, Sendai 980-8578, Japan, E-mail: [e-mail] Tokiwakai Group, 62 Numajiri Tsuduri-Chou Uchigo Iwaki 973-8053, Japan, E-mail: hisyo@tokiwa.或.jp
• New Sugar Based γ-Amino Silyl Ether Organocatalysts for Asymmetric Michael Addition of β-Keto Esters with Nitroolefins
  作者：Hiroto Nakano、Divakar Ganesan、Perumalsamy Parasuraman、Zubeda Begum、Chigusa Seki、Yuko Okuyama、Eunsang Kwon、Koji Uwai、Michio Tokiwa、Suguru Tokiwa、Mitsuhiro Takeshita、Rajkumar Thiyagarajan

  DOI：10.3987/com-21-s(r)2

  日期：——

  New sugar based γ-amino silyl ether organocatalysts were synthesized and their catalytic ability was examined in asymmetric Michael addition of β-keto esters with nitroolefins affording chiral Michael adducts with quaternary carbon stereocenter in good to excellent chemical yields, diastereoselectivities and moderate enantioselectivities (up to 97%, up to dr. 85:15, up to 56% ee).

  合成了新的基于糖的 γ-氨基甲硅烷基醚有机催化剂，并在 β-酮酯与硝基烯烃的不对称迈克尔加成中检测了它们的催化能力，从而得到具有季碳立体中心的手性迈克尔加合物，具有良好至优异的化学收率、非对映选择性和中等对映选择性（高达97%，高达85:15博士，高达 56% ee )。