(R)-tert-butyl 3-hydroxydecanoate | 63741-29-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-tert-butyl 3-hydroxydecanoate
• 英文别名: (+) R-β-hydroxy n-decanoate de t-butyle；(R)-3-hydroxydecanoic acid t-butyl ester；tert-Butyl (3R)-3-hydroxydecanoate
• CAS: 63741-29-7
• 化学式: C₁₄H₂₈O₃
• 分子量: 244.375
• InChiKey: WRUQBBMDEHYWKE-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-tert-butyl 3-hydroxydecanoate 在 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 7.0h， 生成
  参考文献：
  名称：

  Efficient Syntheses of a Series of Trehalose Dimycolate (TDM)/Trehalose Dicorynomycolate (TDCM) Analogues and Their Interleukin-6 Level Enhancement Activity in Mice Sera

  摘要：

  We found an IL-6 level-enhancing compound during our synthetic study of trehalose-6,6'-dimycolate (1, TDM, formerly called cord factor) analogues. TDM is a glycolipid distributed in the cell wall of Mycobacterium tuberculosis and shows significant antitumor activity based on an immunoadjuvant activity. However, due to its significant toxicity, TDM is not yet applicable for practical use. In 1993, Datta and Takayama reported the purification of trehalose-6,6'-dicorynomycolate (2c, TDCM) from Corynebacterium spp. We have previously reported the synthesis of four diastereomeric TDCMs and showed that the synthetic (2R,3R,2'R,3'R)-TDCM (2c, hereafter abbreviated RRRR-TDCM-C-14) is identical to natural TDCM; we also demonstrated that 2c and SSSS-TDCM-C-14 (3c) showed significant antitumor activity as well as inhibitory activity in experimental lung metastasis based on the immunoadjuvant activity. Furthermore, we found that the significant lethal toxicity in mice by TDM (1) was no longer observed with the shorter-chain analogues of TDCMs. Therefore, we have elucidated that the 2,3-antistereochemistry (RR or SS) of the fatty acid residue is promising for biological activities. The chain length of the fatty acid residue should also be important for the biological activity, and thus, we designed a general synthetic procedure for trehalose diesters with 2,3-antistereochemistry and a series of chain lengths by using Noyori's asymmetric reduction of beta,beta-ketoesters followed by antiselective alkylation according to Frater to give beta,beta-hydroxy alcohols as the key steps. Thus, we prepared trehalose diesters (TDCM) 2a-d, 3a-d, and 4a-d as well as monoesters (TMCM) 5a-d and 6a-d. Immunological activities of TDCMs and TMCMs were evaluated by determining IL-6 level enhancement in mouse serum, and we found that RRRR-TDCM-C-14 (2c) and RRSS-TDCM-C-14 (4c) showed significant IL-6 level enhancement activities.

  DOI：

  10.1021/jo062018j
• 作为产物：
  描述：

  1-碘己烷 在 [(S)-2,2'-双(二苯基磷)-1,1'-联萘]二氯化钌(II) 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 73.17h， 生成 (R)-tert-butyl 3-hydroxydecanoate
  参考文献：
  名称：

  Efficient Syntheses of a Series of Trehalose Dimycolate (TDM)/Trehalose Dicorynomycolate (TDCM) Analogues and Their Interleukin-6 Level Enhancement Activity in Mice Sera

  摘要：

  We found an IL-6 level-enhancing compound during our synthetic study of trehalose-6,6'-dimycolate (1, TDM, formerly called cord factor) analogues. TDM is a glycolipid distributed in the cell wall of Mycobacterium tuberculosis and shows significant antitumor activity based on an immunoadjuvant activity. However, due to its significant toxicity, TDM is not yet applicable for practical use. In 1993, Datta and Takayama reported the purification of trehalose-6,6'-dicorynomycolate (2c, TDCM) from Corynebacterium spp. We have previously reported the synthesis of four diastereomeric TDCMs and showed that the synthetic (2R,3R,2'R,3'R)-TDCM (2c, hereafter abbreviated RRRR-TDCM-C-14) is identical to natural TDCM; we also demonstrated that 2c and SSSS-TDCM-C-14 (3c) showed significant antitumor activity as well as inhibitory activity in experimental lung metastasis based on the immunoadjuvant activity. Furthermore, we found that the significant lethal toxicity in mice by TDM (1) was no longer observed with the shorter-chain analogues of TDCMs. Therefore, we have elucidated that the 2,3-antistereochemistry (RR or SS) of the fatty acid residue is promising for biological activities. The chain length of the fatty acid residue should also be important for the biological activity, and thus, we designed a general synthetic procedure for trehalose diesters with 2,3-antistereochemistry and a series of chain lengths by using Noyori's asymmetric reduction of beta,beta-ketoesters followed by antiselective alkylation according to Frater to give beta,beta-hydroxy alcohols as the key steps. Thus, we prepared trehalose diesters (TDCM) 2a-d, 3a-d, and 4a-d as well as monoesters (TMCM) 5a-d and 6a-d. Immunological activities of TDCMs and TMCMs were evaluated by determining IL-6 level enhancement in mouse serum, and we found that RRRR-TDCM-C-14 (2c) and RRSS-TDCM-C-14 (4c) showed significant IL-6 level enhancement activities.

  DOI：

  10.1021/jo062018j

文献信息

• Trehalose compound and pharmaceutical comprising the compound
  申请人：Otsuka Chemical Co., Ltd.

  公开号：US08163713B2

  公开（公告）日：2012-04-24

  The object of the present invention is to provide a novel trehalose compound having a high affinity for an adenosine A3 receptor. The trehalose compound of the present invention is represented by General Formula (1): wherein X and X′ represent a hydrogen atom, and the like; Y and Y′ independently represent an oxygen atom, and the like; R1 and R2 independently represent a C1-C6 alkyl group; and R3 and R4 independently represent a C3-C6 alkyl group. The trehalose compound of the present invention has a remarkably high affinity for an adenosine A3 receptor.

  本发明的目的是提供一种新颖的海藻糖化合物，具有高亲和力与腺苷A3受体结合。本发明的海藻糖化合物由通式（1）表示：其中X和X'代表氢原子等；Y和Y'各自独立表示氧原子等；R1和R2各自独立表示C1-C6烷基；R3和R4各自独立表示C3-C6烷基。本发明的海藻糖化合物与腺苷A3受体具有极高的亲和力。
• Komplexe mit optisch aktiven Zuckerliganden, Verfahren zu deren Herstellung und deren Verwendung
  申请人：CIBA-GEIGY AG

  公开号：EP0254685A2

  公开（公告）日：1988-01-27

  Verbindungen der Formeln I und la worin R1 eine auf Carbonyl- oder Iminverbindungen übertragbare Gruppe, z.B. Alkyl, Allyl, Vinyl oder der Rest eines Enols oder Enamins, R2 z.B. Cyclopentadienyl, R3 der Rest eines optisch aktiven Zuckers oder Zuckerderivats, Me Ti, Zr oder Hf, x = 0, 1, 2 und y = 0, 1, 2, 3, M⊕ für Li⊕, Na⊕, K⊕, MgY⊕, ZnY⊕, CdY⊕, HgY⊕, CuY⊕ oder quatemäres Ammonium stehen, worin Y Halogen bedeutet, eignen sich als chirale Reaktanden für Verbindungen mit Aldehyd-, Keto- und/oder N-substituierten imingruppen.

  式 I 和 la 的化合物 其中 R1 是可转移至羰基或亚胺化合物的基团，如烷基、烯丙基、乙烯基或烯醇或烯胺的基团，R2 是环戊二烯基，R3 是具有光学活性的糖或糖衍生物的残基，如 Me Ti、Zr 或 Hf，x = 0、1、2 和 y = 0、1、2 和 y。HgY⊕、CuY⊕或季铵（其中 Y 为卤素）适合作为具有醛基、酮基和/或 N-取代亚胺基团的化合物的手性反应物。
• TREHALOSE COMPOUND AND PHARMACEUTICAL COMPRISING THE COMPOUND
  申请人：Otsuka Chemical Co., Ltd.

  公开号：EP2000473B1

  公开（公告）日：2011-04-06
• Duthaler, Rudolf O.; Herold, Peter; Lottenbach, Willy, Angewandte Chemie, 1989, vol. 101, # 4, p. 490 - 491
  作者：Duthaler, Rudolf O.、Herold, Peter、Lottenbach, Willy、Oertle, Konrad、Riediker, Martin

  DOI：——

  日期：——
• Syntheses asymetriques de β-hydroxyacides par condensation d'anions enolates d'esters α-sulfinyle chiraux sur des composes carbonyles
  作者：Charles Mioskowski、Guy Solladie

  DOI：10.1016/0040-4020(80)80010-x

  日期：1980.1