(R)-3-benzyloxy-1-(methanesulfonyloxy)tetradecane | 137119-93-8

• 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: (R)-3-benzyloxy-1-(methanesulfonyloxy)tetradecane
• 英文别名: [(3R)-3-phenylmethoxytetradecyl] methanesulfonate
• CAS: 137119-93-8
• 化学式: C₂₂H₃₈O₄S
• 分子量: 398.607
• InChiKey: NYGUYLXUNLATMP-JOCHJYFZSA-N

物化性质

• 沸点：
  520.8±33.0 °C(Predicted)
• 密度：
  1.028±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  27
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-3-benzyloxy-1-(methanesulfonyloxy)tetradecane 在 [C₈H₁₂Ir(PMePh₂)2]PF₆ 、 氢气 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 2,2,2-trichloroethylimidoyl 2-azido-3-O-[(R)-3-(benzyloxy)tetradecyl]-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of GLA-60 type pyran carboxylic acids with an alkyl chain instead of an ester chain as LPS-antagonists

  摘要：

  Synthesis of GLA-60 type pyran carboxylic acid analogues with an alkyl chain instead of an ester chain and their LPS-antagonist activity toward human U937 cells are described. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00055-6
• 作为产物：
  描述：

  (R)-(-)-3-羟基十四烷酸 在 吡啶 、 lithium aluminium tetrahydride 、 sodium hydride 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 22.25h， 生成 (R)-3-benzyloxy-1-(methanesulfonyloxy)tetradecane
  参考文献：
  名称：

  2-脱氧-2-[（（3R）-3-羟基十四烷酰胺基] -3-O-[（3R）-3-羟基四癸基]-α-D-吡喃葡萄糖基磷酸二氢盐和2-脱氧-2-[（3R）的合成-3-羟基十四烷酰胺基] -3-O-[（3R）-3-羟基十四烷基] -4-O-膦酰基-D-吡喃葡萄糖。

  摘要：

  Both a 3-O-alkyl lipid X analogue and its 4-O-phosphono isomer were synthesized from allyl 2-deoxy-4,6-O-isopropylidene-2-trifluoroacetamido-alpha-D-glucopyranoside.

  DOI：

  10.1016/0008-6215(91)89006-2

文献信息

• Ether type lipid a 1-carboxylic acid analogs
  申请人：SANKYO COMPANY, LIMITED

  公开号：US20020161221A1

  公开（公告）日：2002-10-31

  A compound of formula (I) below, which exhibits excellent macrophage activity inhibitory action, is useful for the treatment or prophylaxis of inflammatory disorders, autoimmune diseases or septicemia. In a preferred embodiment, R 1 and R 3 each represents a C 1 -C 20 alkanoyl group which may optionally be substituted with one or more substituent groups selected from substituent group A, R 2 and R 4 each represents a C 1 -C 20 alkyl group which may optionally be substituted with one or more substituent groups selected from substituent group A, R 5 is a hydrogen atom, a halogen atom, a hydroxy group, or a C 1 -C 6 alkoxy group, and substituent group A is a halogen atom, a hydroxy group, an oxo group, a C 1 -C 20 alkoxy group, or a C 1 -C 20 alkanoyloxy group. 1

  以下为化合物式（I），该化合物表现出出色的巨噬细胞活性抑制作用，可用于治疗或预防炎症性疾病、自身免疫性疾病或败血症。在首选实施例中，R1和R3各代表一个C1-C20烷酰基团，该基团可以选择性地被一个或多个取代基团A所取代，R2和R4各代表一个C1-C20烷基团，该基团可以选择性地被一个或多个取代基团A所取代，R5是氢原子、卤素原子、羟基或C1-C6烷氧基团，取代基团A是卤素原子、羟基、氧代基、C1-C20烷氧基团或C1-C20烷酰氧基团。
• ETHER TYPE LIPID A1-CARBOXYLIC ACID ANALOGUES
  申请人：Sankyo Company, Limited

  公开号：EP1152007A1

  公开（公告）日：2001-11-07

  A compound of formula (I), which exhibits excellent macrophage activity inhibitory action, is useful for the treatment or prophylaxis of inflammatory disorders. autoimmune diseases or septicemia. R1 and R3 each represents a C1-C20 alkanoyl group which may optionally be substituted with one or more substituent groups selected from substituent group A, R2 and R4 each represents a C1-C20 alkyl group which may optionally be substituted with one or more substituent groups selected from substituent group A, R5 is a hydrogen atom, a halogen atom, a hydroxy group, or a C1-C6 alkoxy group, and Substituent group A is a halogen atom, a hydroxy group, an oxo group, a C1-C20 alkoxy group, or a C1-C20 alkanoyloxy group.

  式（I）化合物具有出色的巨噬细胞活性抑制作用，可用于治疗或预防炎症性疾病、自身免疫性疾病或败血症。 R1 和 R3 各自代表 C1-C20 烷酰基，可任选被一个或多个选自取代基 A 的取代基取代、 R2 和 R4 各自代表一个 C1-C20 烷基，可任选被一个或多个选自取代基 A 的取代基取代、 R5 是氢原子、卤素原子、羟基或 C1-C6 烷氧基，取代基 A 是卤素原子、羟基、氧代基团、C1-C20 烷氧基或 C1-C20 烷酰氧基。
• Synthesis of lipid A type carboxymethyl derivatives with ether chains instead of ester chains and their LPS-antagonistic activities
  作者：Yukiko Watanabe、Kumiko Miura、Masao Shiozaki、Saori Kanai、Shin-ichi Kurakata、Masahiro Nishijima

  DOI：10.1016/s0008-6215(02)00357-9

  日期：2003.1

  Synthesis of lipid A type carboxymethyl derivatives having ether chains at both the C-3 and C-3' positions and their LPS-antagonistic activities toward human U937 cells are described. (C) 2002 Elsevier Science Ltd. All rights reserved.
• US6511965B2
  申请人：——

  公开号：US6511965B2

  公开（公告）日：2003-01-28
• Synthesis of 2-deoxy-2-[(3R)-3-hydroxytetradecanamido]-3-O-[(3R)-3-hydroxytetradecanyl]-α-d-glucopyranosyl dihydrogen phosphate and 2-deoxy-2-[(3R)-3-hydroxy-tetradecanamido]-3-O-[3R)-3-hydroxytetradecanyl]-4-O-phosphono-d-glucopyranose
  作者：Masao Shiozaki、Yoshiyuki Kobayashi、Noboru Ishida、Masami Arai、Tetsuo Hiraoka、Masahiro Nishijima、Sayuri Kuge、Toshiaki Otsuka、Yuzuru Akamatsu

  DOI：10.1016/0008-6215(91)89006-2

  日期：1991.12

  Both a 3-O-alkyl lipid X analogue and its 4-O-phosphono isomer were synthesized from allyl 2-deoxy-4,6-O-isopropylidene-2-trifluoroacetamido-alpha-D-glucopyranoside.