(S)-(+)-(benzyloxy)methyl 3-<(benzyloxy)methoxy>-2-methylpropionate | 116021-11-5

• 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: (S)-(+)-(benzyloxy)methyl 3-<(benzyloxy)methoxy>-2-methylpropionate
• 英文别名: (S)-(+)-(benzyloxy)methyl 3-[(benzyloxy)methoxy]-2-methylpropionate；methyl (S)-3-benzyloxymethyloxy-2-methylpropionate；methyl (2S)-2-methyl-3-(phenylmethoxymethoxy)propanoate
• CAS: 116021-11-5
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: UFMUWQHQKRSDBZ-NSHDSACASA-N

物化性质

• 沸点：
  321.4±22.0 °C(Predicted)
• 密度：
  1.076±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-(+)-(benzyloxy)methyl 3-<(benzyloxy)methoxy>-2-methylpropionate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 (S)-(+)-3-<(benzyloxy)methoxy>-2-methylpropanal
  参考文献：
  名称：

  Synthesis of an avermectin-nemadectin hybrid.

  摘要：

  The Wittig condensation of (2R,3R,4E)-2,6-dimethyl-3-trimethylsilyloxy-4-heptenyltriphenylphosphorylidene with aldehyde 1 produced the desired cis olefin 11 in 45% yield. Treatment of this intermediate with pyridinium tosylate in methanol effected spiroketalization and desilylation with hydrogen fluoride-pyridine in THF afforded the avermectin-nemadectin hybrid 2.

  DOI：

  10.1016/s0040-4039(00)79760-7
• 作为产物：
  描述：

  苄基氯甲基醚 、 (S)-(+)-3-羟基异丁酸甲酯 在 N,N-二异丙基乙胺 作用下， 反应 12.0h， 以100%的产率得到(S)-(+)-(benzyloxy)methyl 3-<(benzyloxy)methoxy>-2-methylpropionate
  参考文献：
  名称：

  The first total synthesis of the antitumor macrolide rhizoxin: Synthesis of the key building blocks

  摘要：

  The construction in optically pure form of the key building blocks, arising from our retrosynthetic analysis of the antitumor macrolide rhizoxin is described.

  DOI：

  10.1016/s0040-4039(00)77485-5

文献信息

• Stereocontrolled and Convergent Total Synthesis of Amphidinolide T3
  作者：Li-Sheng Deng、Xiao-Ping Huang、Gang Zhao

  DOI：10.1021/jo0605086

  日期：2006.6.1

  Stereocontrolled and convergent total synthesis of amphidinolide T3 has been described. A retrosynthetic scheme was constructed that led to the recognition of readily available and enantiomerically related compounds as starting materials for the total synthesis of amphidinolide T3. Thus, the two key building blocks 6 and 7 were defined as subtargets and synthesized in optically active forms. The C1−C12

  已经描述了立体控制的和会聚的安非他命T3的全合成。构建了逆合成方案，该方案导致了容易获得的和对映异构相关的化合物被识别为完全合成两性霉素T3的起始原料。因此，将两个关键构件6和7定义为子目标，并以光学活性形式合成。C1-C12片段6衍生自市售的d-谷氨酸或其合成等效物（R）-5-羟甲基四氢呋喃-2-酮16，作为起始原料，涉及高度非对映选择性不对称烯丙基化为关键步骤。C13-C21片段7通过链段10和碘化物11的二噻吩偶联，以高收率高效地合成苯并噻吩，随后进行脱保护和Petasis烯化。最终，片段醛6和二噻吩7的组装以及C-C键的形成，两步氧化还原序列，选择性大环内酯化和功能转变提供了两性化合物A3和T4的收敛的全部和形式合成，这种方法还提供了一种灵活而实用的两性霉素T大环内酯的合成方法。
• 3(1-hydoxyethyl)azetidinone compounds and their production
  申请人：Sumitomo Pharmaceuticals Company, Limited

  公开号：US05134231A1

  公开（公告）日：1992-07-28

  An amino acid compound of the formula: ##STR1## wherein R is a lower alkyl group, R.sub.1 is a hydrogen atom or a protecting group for carboxyl, R.sub.2 is a hydrogen atom, a protecting group for amino, an optionally substituted allyl group of the formula: ##STR2## (wherein R.sub.3 and R.sub.4 are each a hydrogen atom, a lower alkyl group or an aryl group), a beta-hydroxyethyl group in which the hydroxyl group is optionally protected, a formylmethyl group in which the formyl group is optionally protected, a carboxymethyl group in which the carboxyl group is protected or a 2-furylmethyl group and X is an optionally protected carboxyl group, a hydroxymethyl group in which the hydroxyl group is optionally protected or a substituted mercaptomethyl group of the formula: --CH.sub.2 SR.sub.5 (wherein R.sub.5 is an aryl group or an ar(lower)alkyl group), which is a useful intermediate in the synthesis of 1-alkylcarbapenem compounds.

  化合物的氨基酸式：##STR1## 其中R是低碳基团，R.sub.1是羧基的保护基或氢原子，R.sub.2是氨基的保护基、可选取代的烯丙基式：##STR2##（其中R.sub.3和R.sub.4分别是氢原子、低碳基团或芳基团），β-羟乙基基团，其中羟基可以选择性保护，甲酰甲基基团，其中甲酰基可以选择性保护，羧甲基基团，其中羧基被保护或2-呋喃甲基基团，X是可选择性保护的羧基，羟甲基基团，其中羟基可以选择性保护，或取代的巯基甲基基团式：--CH.sub.2 SR.sub.5（其中R.sub.5是芳基团或芳(低)碳基团），该化合物是1-烷基卡巴冬烯类化合物合成中有用的中间体。
• Boeckman Jr., Robert K.; Charette, André B.; Asberom, Theodros, Journal of the American Chemical Society, 1991, vol. 113, # 14, p. 5337 - 5353
  作者：Boeckman Jr., Robert K.、Charette, André B.、Asberom, Theodros、Johnston, Brian H.

  DOI：——

  日期：——
• The first total synthesis of the antitumor macrolide rhizoxin: Synthesis of the key building blocks
  作者：Masahisa Nakada、Susumu Kobayashi、Shigeo Iwasaki、Masaji Ohno

  DOI：10.1016/s0040-4039(00)77485-5

  日期：1993.2

  The construction in optically pure form of the key building blocks, arising from our retrosynthetic analysis of the antitumor macrolide rhizoxin is described.
• Synthesis of an avermectin-nemadectin hybrid.
  作者：Thomas L. Shih、Mark A. Holmes、Helmut Mrozik、Michael H. Fisher

  DOI：10.1016/s0040-4039(00)79760-7

  日期：1991.7

  The Wittig condensation of (2R,3R,4E)-2,6-dimethyl-3-trimethylsilyloxy-4-heptenyltriphenylphosphorylidene with aldehyde 1 produced the desired cis olefin 11 in 45% yield. Treatment of this intermediate with pyridinium tosylate in methanol effected spiroketalization and desilylation with hydrogen fluoride-pyridine in THF afforded the avermectin-nemadectin hybrid 2.