methyl 4-O-benzoyl-2,3,6-trideoxy-α-L-threo-hex-2-enopyranoside | 34385-27-8

• 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: methyl 4-O-benzoyl-2,3,6-trideoxy-α-L-threo-hex-2-enopyranoside
• 英文别名: methyl 4-O-benzoyl-2,3,6-trideoxy-β-L-threo-hex-2-enopyranoside；[(2S,3S,6S)-6-methoxy-2-methyl-3,6-dihydro-2H-pyran-3-yl] benzoate
• CAS: 34385-27-8；61243-00-3；61819-51-0；98291-56-6；100102-48-5；116502-27-3
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: JCLNNKOKZJNLBY-DRZSPHRISA-N

物化性质

• 沸点：
  349.0±42.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  methyl 4-O-benzoyl-2,3,6-trideoxy-α-L-threo-hex-2-enopyranoside 在 三乙基硅烷 、 四氯化钛 作用下， 以86%的产率得到Benzoic acid (2S,3S)-2-methyl-3,6-dihydro-2H-pyran-3-yl ester
  参考文献：
  名称：

  Regioselectivity in the Palladium-Catalyzed Addition of Carbon Nucleophiles to Dihydropyran Derivatives

  摘要：

  The regioselectivity of Pd-catalyzed malonate or sulfonylacetate addition to dihydropyran derivatives is highly dependent upon the substitution pattern of the dihydropyran nucleus and is governed by electronic, rather than steric factors. In certain instances, subtle steric features also play a role in controlling regioselectivity by altering the conformation of the intermediate eta(3)-allyl Pd-complex.

  DOI：

  10.1021/jo961973d
• 作为产物：
  描述：

  methyl 4-O-acetyl-2,3,6-trideoxy-α,β-L-erythro-hex-2-enopyranoside 在 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 15.0h， 生成 methyl 4-O-benzoyl-2,3,6-trideoxy-α-L-threo-hex-2-enopyranoside
  参考文献：
  名称：

  鼠李糖短而有效地转化为活化的柔红胺，二十二胺，香豆胺和表柔红胺衍生物，并合成了蒽环类抗生素二十四胺-ε-异-紫丁香酮。

  摘要：

  3-氨基-2,3,6-三甲氧基己基吡喃糖是大多数蒽环类抗肿瘤抗生素的重要组成部分。为了研究结构-活性关系，从市售鼠李糖开始以短而有效的途径合成了四种非对映体氨基糖柔红胺，二十二胺，香豆胺和表柔红胺。提供了几种糖基供体，其用途在合成氨糖基-ε-异二十四烯酮中得到了例证。

  DOI：

  10.1016/s0008-6215(00)00257-3

文献信息

• Total Synthesis of the Postulated Structure of Fulicineroside
  作者：Ruben Bartholomäus、Fabian Dommershausen、Markus Thiele、Narayan S. Karanjule、Klaus Harms、Ulrich Koert

  DOI：10.1002/chem.201204545

  日期：2013.6.3

  A total synthesis of the proposed structures of fulicineroside and its aglycone fulicinerine is reported. The tetrasubstituted dibenzofuran substructure was accessible either through a Pd‐mediated ortho‐metalation or by an Ir‐catalyzed meta‐borylation. The synthesis of the β,β,α‐linked trisaccharide consisting of D‐olivose, L‐rhodinose, and L‐rhamnose was challenged by the unprecedented β‐linked rhodinose

  报道了黄腐苷和其糖苷配基黄嘌呤碱的建议结构的全合成。四取代的二苯并呋喃亚结构可通过Pd介导的原金属化或通过Ir催化的间硼化来获得。由D-寡糖，L-罗丹糖和L-鼠李糖组成的β，β，α-连接的三糖的合成受到前所未有的β-连接的罗丹糖的挑战。Pd催化的4-表位-若丹糖的β-选择性糖基化反应和随后的Mitsunobu倒置可选择性地提供β-连接的L-若丹糖-L鼠李糖二糖。与天然产物和糖苷配基的报道数据进行比较表明，天然产物的结构分配有误。
• Regioselectivity in the Palladium-Catalyzed Addition of Carbon Nucleophiles to Dihydropyran Derivatives
  作者：Marc-Raleigh Brescia、Yvonne Class Shimshock、Philip DeShong

  DOI：10.1021/jo961973d

  日期：1997.3.1

  The regioselectivity of Pd-catalyzed malonate or sulfonylacetate addition to dihydropyran derivatives is highly dependent upon the substitution pattern of the dihydropyran nucleus and is governed by electronic, rather than steric factors. In certain instances, subtle steric features also play a role in controlling regioselectivity by altering the conformation of the intermediate eta(3)-allyl Pd-complex.
• A short and efficient transformation of rhamnose into activated daunosamine, acosamine, ristosamine and epi-daunosamine derivatives, and synthesis of an anthracycline antibiotic acosaminyl-ε-iso-rhodomycinone
  作者：Bernd Renneberg、Yue-Ming Li、Hartmut Laatsch、Heinz-Herbert Fiebig

  DOI：10.1016/s0008-6215(00)00257-3

  日期：2000.12

  constituents of most anthracycline antitumour antibiotics. For an investigation of structure-activity relationships, the four diastereomeric amino sugars daunosamine, acosamine, ristosamine, and epi-daunosamine were synthesised in short and efficient routes starting from commercially available rhamnose. Several glycosyl donors were provided and their use was exemplified in the synthesis of acosaminyl-e

  3-氨基-2,3,6-三甲氧基己基吡喃糖是大多数蒽环类抗肿瘤抗生素的重要组成部分。为了研究结构-活性关系，从市售鼠李糖开始以短而有效的途径合成了四种非对映体氨基糖柔红胺，二十二胺，香豆胺和表柔红胺。提供了几种糖基供体，其用途在合成氨糖基-ε-异二十四烯酮中得到了例证。