3-(1-tert-butyldimethylsiloxy)ethyl-4-phenylsulfinylazetidin-2-one | 144069-72-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 3-(1-tert-butyldimethylsiloxy)ethyl-4-phenylsulfinylazetidin-2-one
• 英文别名: (3S,4R)-3-[(1R)-1-t-Butyldimethylsilyloxyethyl]-4-phenylsulfinylazetidin-2-one；(3S,4R)-4-(benzenesulfinyl)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]azetidin-2-one
• CAS: 144069-72-7
• 化学式: C₁₇H₂₇NO₃SSi
• 分子量: 353.558
• InChiKey: KWZXHRIVBFMGNS-PSCDEBNHSA-N

物化性质

• 沸点：
  495.0±30.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  74.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(1-tert-butyldimethylsiloxy)ethyl-4-phenylsulfinylazetidin-2-one 在 zinc(II) iodide 叠氮基三甲基硅烷 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以100%的产率得到(3S,4R)-4-azido-3-<(1R)-(1-tert-butyldimethylsiloxy)ethyl>azetidin-2-one
  参考文献：
  名称：

  An Efficient Synthesis of 4-Heterofunction-Substituted 3-(1-Hydroxy)ethylazetidin-2-ones from 3-(1-Hydroxy)ethyl-4-phenylsulfinylazetidin-2-one by Reaction with Silylated Heteronucleophiles.

  摘要：

  在催化量 ZnI2 的存在下，3-(1-叔丁基二甲基硅氧基)乙基-4-亚磺酰基氮杂环丁烷-2-酮与硅烷化的 N-、S-、O-和 P-亲核物发生反应，得到相应的反式-4-杂环丁烷-2-酮高倍率化合物。

  DOI：

  10.1248/cpb.40.1733
• 作为产物：
  描述：

  (3S,4R)-3-<(1R)-(1-tert-butyldimethylsiloxy)ethyl>-4-phenylthioazetidin-2-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以84%的产率得到3-(1-tert-butyldimethylsiloxy)ethyl-4-phenylsulfinylazetidin-2-one
  参考文献：
  名称：

  A Novel Method for the Alkoxylation of Azetidin-2-ones at the 4-Position.

  摘要：

  在一定量的三甲基硅基三氟甲磺酸盐催化下，4-亚磺酰基氮杂环丁烷-2-酮与各种类型的三丁基锡烷氧基化合物发生反应，以高产率得到相应的反式烷氧基氮杂环丁烷-2-酮。

  DOI：

  10.1248/cpb.40.1044

文献信息

• Carbapenem
  申请人：Sankyo Company, Limited

  公开号：US05614624A1

  公开（公告）日：1997-03-25

  A compound of the formula ##STR1## in which: R.sup.1' is hydrogen or a carboxy-protecting group; R.sup.41' is hydrogen or a hydroxy-protecting group; R.sup.42' is a C.sub.1 -C.sub.6 alkyl, a C.sub.1 -C.sub.6 alkoxy, a halogen, an aryl or an aryloxy; R.sup.43' is hydrogen, a C.sub.1 -C.sub.6 alkyl, a C.sub.1 -C.sub.6 alkoxy, a hydroxy, a halogen, a cyano, a nitro or a group of the formula --NR.sup.8' R.sup.9', where R.sup.8' and R.sup.9' are independently selected from the group consisting of hydrogen, amino-protecting groups, C.sub.1 -C.sub.6 alkyl groups and phenyl groups, or R.sup.8' and R.sup.9' together represent a group --(CH.sub.2).sub.q '--O.sub.r '--(CH.sub.2).sub.s '--, where q' and s' are independently 0 or an integer of from 1 to 5 and r' is 0 or 1, provided that (q'+s') is an integer of at least 2; R.sup.45' and R.sup.46' are independently selected from the group consisting of C.sub.1 -C.sub.6 alkyl groups and aryl groups, or R.sup.45' and R.sup.46' together represent a group --(CH.sub.2).sub.q '--O.sub.r '--(CH.sub.2).sub.s '--, where q' and s' are independently 0 or an integer of from 1 to 5 and r' is 0 or 1; Y' is oxygen or sulfur; and j' is 0, 1 or 2.

  该化合物的结构式为##STR1##其中：R.sup.1'为氢或羧基保护基；R.sup.41'为氢或羟基保护基；R.sup.42'为C.sub.1-C.sub.6烷基，C.sub.1-C.sub.6烷氧基，卤素，芳基或芳氧基；R.sup.43'为氢，C.sub.1-C.sub.6烷基，C.sub.1-C.sub.6烷氧基，羟基，卤素，氰基，硝基或式--NR.sup.8'R.sup.9'的基团，其中R.sup.8'和R.sup.9'独立地选择自羟基保护基，C.sub.1-C.sub.6烷基和苯基的群，或R.sup.8'和R.sup.9'在一起表示式--(CH.sub.2).sub.q '--O.sub.r '--(CH.sub.2).sub.s '--的基团，其中q'和s'独立地为0或从1到5的整数，r'为0或1，前提是(q'+s')至少为2的整数；R.sup.45'和R.sup.46'独立地选择自C.sub.1-C.sub.6烷基和芳基，或R.sup.45'和R.sup.46'在一起表示式--(CH.sub.2).sub.q '--O.sub.r '--(CH.sub.2).sub.s '--的基团，其中q'和s'独立地为0或从1到5的整数，r'为0或1；Y'为氧或硫；j'为0、1或2。
• Metal catalyzed displacement process
  申请人：Sankyo Company, Limited

  公开号：US05681951A1

  公开（公告）日：1997-10-28

  A process for preparing a compound of formula (I'): ##STR1## comprising reacting a compound of formula (II'): ##STR2## with a compound of formula (III'): A'SH (III') wherein the reaction of the compound of formula (II') and the compound of formula (III') are carried out in the presence of a salt of a metal of Group II or III of the Periodic Table of Elements, wherein A' is an alkyl, aryl, aralkyl or heterocyclic, R.sup.1' is hydrogen or a carboxy protecting group, R.sup.2' and R.sup.3' can be hydrogen or alkyl, X' can be sulfur, k' is 1 or 2 and R.sup.4' is alkyl, alkenyl, aryl, aralkyl, cycloalkyl or heterocyclic.

  一种制备式（I'）化合物的方法： ##STR1## 包括将式（II'）化合物与式（III'）化合物反应： ##STR2## 其中化合物（II'）和化合物（III'）的反应在元素周期表II或III族金属的盐的存在下进行，其中A'是烷基，芳基，芳烷基或杂环基，R.sup.1'是氢或羧基保护基，R.sup.2'和R.sup.3'可以是氢或烷基，X'可以是硫，k'为1或2，R.sup.4'是烷基，烯基，芳基，芳烷基，环烷基或杂环基。
• Azetidinone compounds useful in the preparation of carbapenem
  申请人：Sankyo Company, Limited

  公开号：US05541317A1

  公开（公告）日：1996-07-30

  Compounds of formula (I): ##STR1## wherein: R.sup.1 is hydrogen or a hydroxy-protecting group; R.sup.2 is alkyl, alkoxy, halogen, optionally substituted phenyl or optionally substituted phenoxy; R.sup.3 is optionally substituted pyridyl, optionally substituted quinolyl or phenyl group which has a substituent of formula --CYNR.sup.5 R.sup.6, where Y is oxygen or sulfur, and R.sup.5 and R.sup.6 are each alkyl, aryl or aralkyl, or R.sup.5 and R.sup.6 and the nitrogen to which they are attached together form a heterocyclic group; is R.sup.4 hydrogen or an amino-protecting group; and Z is sulfur or oxygen; are valuable intermediates in the preparation of carbapenem compounds and retain a desirable configuration during conversion to such carbapenem compounds. Penem and carbapenem compounds having a group of formula --SA' are prepared from a corresponding compound having a substituted thio, sulfinyl or sulfonyl group at this position by reaction with a compound A'SH (where A' is an organic group) in the presence of a salt of a metal of Group II or III of the Periodic Table.

  化合物的式子(I)：##STR1## 其中：R.sup.1为氢或羟基保护基；R.sup.2为烷基，烷氧基，卤素，可选择取代的苯基或可选择取代的苯氧基；R.sup.3为可选择取代的吡啶基，可选择取代的喹啉基或具有式子--CYNR.sup.5 R.sup.6的取代基的苯基，其中Y为氧或硫，而R.sup.5和R.sup.6均为烷基，芳基或芳基烷基，或R.sup.5和R.sup.6以及它们所连接的氮共同形成一个杂环基团；R.sup.4为氢或氨基保护基；Z为硫或氧；是制备碳青霉烯化合物的有价值的中间体，并在转化为碳青霉烯化合物期间保持理想的构型。具有式子--SA'的青霉烯和碳青霉烯化合物是通过与具有该位置的取代硫，亚砜或磺酰基的相应化合物在周期表第二或第三组金属的盐存在下与化合物A'SH（其中A'是有机基团）反应制备的。
• Silyl enol ether alkylation process
  申请人：Sankyo Company, Limited

  公开号：US05719275A1

  公开（公告）日：1998-02-17

  A method for preparing compounds of formula (I): ##STR1## wherein: R.sup.1 is hydrogen or a hydroxy-protecting group; R.sup.2 is alkyl, alkoxy, halogen, optionally substituted phenyl or optionally substituted phenoxy; R.sup.3 is optionally substituted pyridyl, optionally substituted quinolyl or phenyl group which has a substituent of formula --CYNR.sup.5 R.sup.6, where Y is oxygen or sulfur, and R.sup.5 and R.sup.6 are each alkyl, aryl or aralkyl, or R.sup.5 and R.sup.6 and the nitrogen to which they are attached together form a heterocyclic group; R.sup.4 is hydrogen or an amino-protecting group; and Z is sulfur or oxygen. The process comprises reacting a compound of formula (II): ##STR2## in which R.sup.8, R.sup.9 and R.sup.10 are the same or different and each represents an alkyl group having from 1 to 4 carbon atoms or a phenyl group, with a compound of formula (III): ##STR3## in which R.sup.11 represents an acyloxy, alkylsulfonyl, arylsulfonyl, alkylsulfinyl or arylsulfinyl group.

  一种制备式（I）化合物的方法：其中：R.sup.1是氢或羟基保护基；R.sup.2是烷基，烷氧基，卤素，可选地取代的苯基或可选地取代的苯氧基；R.sup.3是可选地取代的吡啶基，可选地取代的喹啉基或具有式--CYNR.sup.5 R.sup.6的取代基的苯基，其中Y是氧或硫，R.sup.5和R.sup.6分别是烷基，芳基或芳烷基，或R.sup.5和R.sup.6和它们所连接的氮共同形成一个杂环基；R.sup.4是氢或氨基保护基；Z是硫或氧。该过程包括将式（II）的化合物与式（III）的化合物反应：其中R.sup.8，R.sup.9和R.sup.10相同或不同，每个代表具有1至4个碳原子的烷基或苯基。其中，式（II）为：##STR2##式（III）为：##STR3##
• Kita, Yasuyuki; Shibata, Norio; Tohjo, Takashi, Journal of the Chemical Society. Perkin transactions I, 1992, # 14, p. 1795 - 1800
  作者：Kita, Yasuyuki、Shibata, Norio、Tohjo, Takashi、Yoshida, Naoki

  DOI：——

  日期：——