- Chiral side chain of rosuvastatin calcium containing sulfone structure as well as preparation method and application of chiral side chain
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The invention discloses a chiral side chain of rosuvastatin calcium containing a sulfone structure as well as preparation method and application of the chiral side chain. The chiral side chain D4-2 is prepared by taking D1-1 containing a thioether structure as a precursor; The D1-1 containing the thioether structure (Rz-S-) is synthesized through a brand-new process route and is further converted into a chiral side chain D4-2 containing the sulfone structure (Rz-SO2-), so that the separation and purification process of an intermediate is simplified; and after being modified by a sulfydryl-containing compound D1-M, the originally oily reaction intermediate is changed into a solid, so that the separation and purification effects of the intermediate are greatly improved. The chiral side chain D4-2 is used for preparing a high-grade intermediate R1 for synthesizing rosuvastatin calcium, the quality of R1 can be guaranteed, various indexes of the R1 product are excellent, and the cost is reduced; and the chiral side chain D4-2 is suitable for large-scale industrial production.
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Paragraph 0034; 0036-0040
(2021/04/21)
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- Method for synthesizing ADA
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The invention relates to a compound synthesized in the medicine field, and particularly relates to a rosuvastatin intermediate. The method for synthesizing ADA comprises the following five steps: 1, reacting S-4-chloro-3-hydroxy butyronitrile with hexamethyl-disilazane to generate an intermediate I; 2, reacting the prepared intermediate I, a reducing agent and methanesulfonic acid with tert-butyl bromoacetate to prepare an intermediate II; 3, preparing an intermediate III from the prepared intermediate II by enzyme selective reduction; 4, reacting the prepared intermediate III with acetone acetal to prepare an intermediate IV; and 5, reacting the prepared intermediate IV and tetrabutylammonium bromide with sodium acetate to prepare the target intermediate ADA. According to the method, operation for preparing ADA is more convenient; and the method has high safety coefficient and low cost, and is very suitable for industrial production.
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Paragraph 0081; 0083; 0084; 0085; 0102
(2018/02/04)
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- Stereoselective reduction of δ-hydroxy β-ketoesters to syndiol in achiral micellar system
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A novel, efficient and stereo-selective process for synthesis of statin side chain, a key intermediate for statin type cholesterol lowering drugs such as Lipitor (atorvastatin) and Crestor (rosuvastatin) in achiral micellar media is reported. The key feature of this process is sodium borohydride reduction of δ-hydroxy β-ketoester in achiral micellar system in 92% de, thereby avoiding metal chelation methods which employ triakylborane, titanium (IV) isopropoxide or cerium (III) chloride prior to reduction.
- Roy, Bhairab Nath,Singh, Girij Pal,Lathi, Piyush Suresh,Agrawal, Manoj K,Mitra, Rangan
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p. 1247 - 1251
(2015/11/24)
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- Asymmetric ring opening of epoxides with cyanides catalysed by chiral binuclear titanium complexes
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A series of Schiff bases obtained from salicylaldehydes and 3,3′-diformyl-BINOL were synthesized. The complexes of these Schiff bases with Ti(IV) were active for the asymmetric ring opening of epoxides with TMSCN. A mixture of unpurified ligands was found
- Maleev, Victor I.,Chusov, Denis A.,Yashkina, Lidiya V.,Ikonnikov, Nikolai S.,Il'In, Michail M.
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p. 838 - 843
(2014/06/23)
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- A NOVEL, GREEN AND COST EFFECTIVE PROCESS FOR SYNTHESIS OF TERT-BUTYL (3R,5S)-6-OXO-3,5-DIHYDROXY-3,5-O-ISOPROPYLIDENE-HEXANOATE
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The present invention provides a process of preparation of an intermediate useful for the preparation of statins more particularly the present invention relates to an eco-friendly and cost effective process for the preparation of tert -butyl (3R,5S)-6-oxo-3,5-dihydroxy- 3,5-O-isopropylidene-hexanoate [I].
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Page/Page column 34; 35
(2015/01/07)
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- Efficient activation of zinc: Application of the Blaise reaction to an expedient synthesis of a statin intermediate
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Efficient and practical in situ zinc activation was accomplished by treatment with catalytic amount of an organic acid. The protocol was applied successfully to the Blaise reaction of various nitriles. Noteworthy is the excellent Blaise transformation of (S)-4-chloro-3-trimethylsilyloxybutyronitrile (2b) into tert-butyl (S)-6-chloro-5-hydroxy-3-oxohexanoate (1), a key intermediate for the preparation of HMG-CoA reductase inhibitors (statins).
- Shin, Hyunik,Choi, Bo Seung,Lee, Ki Kon,Choi, Hyeong-Wook,Chang, Jay Hyok,Lee, Kyu Woong,Nam, Do Hyun,Kim, No-Soo
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p. 2629 - 2632
(2007/10/03)
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