1,2:5,6-di-O-isopropylidene-3-C-methyl-3-O-allyl-α-D-allofuranose | 174019-53-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2:5,6-di-O-isopropylidene-3-C-methyl-3-O-allyl-α-D-allofuranose
• 英文别名: 3-O-allyl-1,2:5,6-di-O-isopropylidene-3-C-methyl-α-D-allofuranose；(3aR,5R,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2,6-trimethyl-6-prop-2-enoxy-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxole
• CAS: 174019-53-5
• 化学式: C₁₆H₂₆O₆
• 分子量: 314.379
• InChiKey: DSBDOMUOHDJOSI-GUYIQFIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2:5,6-di-O-isopropylidene-3-C-methyl-3-O-allyl-α-D-allofuranose 在 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 (R)-4-((3aR,5R,6R,6aR)-6-Allyloxy-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-[1,3]dioxolan-2-one
  参考文献：
  名称：

  Synthetic studies on zoapatanol: Construction of oxepanes via an intramolecular 1,3-dipolar cycloaddition strategy

  摘要：

  The nitrones derived from beta-allyloxyaldehydes with a beta-quaternary centre cyclized to give six- instead of seven-membered O-heterocycles exclusively whereas a nitrile oxide derived from a gamma-allyloxyaldehyde with a gamma-quaternary centre cyclized to yield an oxepane ring as the sole product. Using the latter intramolecular nitrile oxide cycloaddition as the key step, optically active oxepane 5, which is a suitable intermediate for a synthesis of zoapatanol 1, has been constructed from D-glucose. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00149-8
• 作为产物：
  描述：

  1,2:5,6-二-o-异亚丙基-alpha-d-ribo-3-己呋喃核糖 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 15.5h， 生成 1,2:5,6-di-O-isopropylidene-3-C-methyl-3-O-allyl-α-D-allofuranose
  参考文献：
  名称：

  Synthetic studies on zoapatanol: Construction of oxepanes via an intramolecular 1,3-dipolar cycloaddition strategy

  摘要：

  The nitrones derived from beta-allyloxyaldehydes with a beta-quaternary centre cyclized to give six- instead of seven-membered O-heterocycles exclusively whereas a nitrile oxide derived from a gamma-allyloxyaldehyde with a gamma-quaternary centre cyclized to yield an oxepane ring as the sole product. Using the latter intramolecular nitrile oxide cycloaddition as the key step, optically active oxepane 5, which is a suitable intermediate for a synthesis of zoapatanol 1, has been constructed from D-glucose. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00149-8

文献信息

• Synthesis of chiral oxepanes and pyrans by 3-O-allylcarbohydrate nitrone cycloaddition (3-OACNC)
  作者：Ashoke Bhattacharjee、Seema Datta、Partha Chattopadhyay、Nanda Ghoshal、Asish P Kundu、Arani Pal、Ranjan Mukhopadhyay、Sandip Chowdhury、Anup Bhattacharjya、Amarendra Patra

  DOI：10.1016/s0040-4020(03)00634-3

  日期：2003.6

  3-O-Allylcarbohydrate nitrone cycloaddition (3-OACNC) furnished pyran and oxepane derivatives from 3-O-allyl hexose N-benzyl nitrones and 3-O-allyl furanoside-5-aldehyde N-benzyl/methyl nitrones. The regioselectivity of 3-OACNC was found to depend on the following factors (a) the structural nature of the nitrone (b) substitution and stereochemistry at 3-C of the carbohydrate backbone (c) substitution

  3- ø从3- -Allylcarbohydrate硝酮环加成（3- OACNC）布置吡喃和氧杂环庚烷衍生物ø -烯丙基己糖ñ -苄基硝酮和3- ö烯丙基呋喃-5-醛ñ -苄基/甲基硝酮。发现3-OACNC的区域选择性取决于以下因素（a）硝酮的结构性质（b）碳水化合物主链在3-C处的取代和立体化学（c）在O末端的取代-烯丙基部分。从特定组的己糖硝酮和相应的呋喃糖苷硝酮获得的氧杂环丁烷或吡喃通过降解转化为对映体环状醚。在3- O-烯丙基碳水合物衍生的肟的分子内肟环烯烃加成反应（IOOC ）中形成环氧丙烷和吡喃的混合物。
• Bhattacharjee, Ashoke; Chattopadhyay, Partha; Kundu, Asish P., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 1, p. 69 - 70
  作者：Bhattacharjee, Ashoke、Chattopadhyay, Partha、Kundu, Asish P.、Mukhopadhyay, Ranjan、Bhattacharjya, Anup

  DOI：——

  日期：——
• Synthesis of enantiomeric pyrans from a 3--allylallose derivative by the application of intramolecular nitrone cycloaddition
  作者：Ashoke Bhattacharjee、Anup Bhattacharjya、Amarendra Patra

  DOI：10.1016/0040-4039(95)00832-w

  日期：1995.6

  The intramolecular nitrone cycloaddition of three sets of 3-O-allylpyranose and the corresponding homochiral 3-O-allylfuranose-5-aldehyde derivatives was studied; one set derived from D-allose gave rise to only pyran derivatives which were converted to enantiomeric pyranoisoxazolidines via minor degradations.
• A convenient approach towards 2′-analogs of zoapatanol from d-glucose
  作者：Huib Ovaa、Gijs A van der Marel、Jacques H van Boom

  DOI：10.1016/s0040-4039(01)00932-7

  日期：2001.8

  The protected 3-C-methyl-alpha -D-allofuranose derivative 6, readily accessible from D-glucose, could be transformed into a diene scaffold which underwent ring-closing metathesis (RCM) to give the functionalized oxepines 10a,b. Further elaboration of 10a,b provided the 2'-zoapatanol analogs 3-5. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthetic studies on zoapatanol: Construction of oxepanes via an intramolecular 1,3-dipolar cycloaddition strategy
  作者：Tony K.M. Shing、Ching-Hung Wong、Ting Yip

  DOI：10.1016/0957-4166(96)00149-8

  日期：1996.5

  The nitrones derived from beta-allyloxyaldehydes with a beta-quaternary centre cyclized to give six- instead of seven-membered O-heterocycles exclusively whereas a nitrile oxide derived from a gamma-allyloxyaldehyde with a gamma-quaternary centre cyclized to yield an oxepane ring as the sole product. Using the latter intramolecular nitrile oxide cycloaddition as the key step, optically active oxepane 5, which is a suitable intermediate for a synthesis of zoapatanol 1, has been constructed from D-glucose. Copyright (C) 1996 Elsevier Science Ltd