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Chemical Structure| 79309-68-5 Chemical Structure| 79309-68-5

Structure of 79309-68-5

Chemical Structure| 79309-68-5

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Product Details of [ 79309-68-5 ]

CAS No. :79309-68-5
Formula : C12H25BO2Si
M.W : 240.22
SMILES Code : C[Si](/C=C/CB1OC(C)(C)C(C)(C)O1)(C)C
MDL No. :MFCD31692669
InChI Key :DKUNISUNFKZEQT-CSKARUKUSA-N
Pubchem ID :11053759

Safety of [ 79309-68-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Application In Synthesis of [ 79309-68-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 79309-68-5 ]

[ 79309-68-5 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 121584-52-9 ]
  • [ 79309-68-5 ]
  • C68H123N11O14Si [ No CAS ]
  • [ 514854-24-1 ]
YieldReaction ConditionsOperation in experiment
With formic acid; acetic acid; at 20 - 22℃; for 2h; 20 G (15.06 mmol, 1 equiv.) of <strong>[121584-52-9]acetyl-cyclosporin A aldehyde</strong> and 5.427 g (22. 59 mmol, 1.5 equiv. ) pinacol complex obtained in i) and 30 ml acetic acid were charged in the reaction vessel at RT under stirring. 30 ML of formic acid were added under water bath cooling, maintaining the temperature between 20-22 C. After 2 hours reaction at RT, 12 ml dichloromethane and 200 ml MTBE were added followed by 120 ml of a 10% aqueous NaCl solution. The water phase was separated and discarded. The organic phase was washed with 120 ml water, 204 ml 2M aqueous NAOH solution and 60 ml water. The organic phase was concentrated at 30 C until the crystallization started. 200 ml MTBE were added and the suspension was concentrated to ca 220 ml. After stirring at RT for 2 hours and for 1 hour at 0-2 C, the suspension was filtered. The solid was washed with 30 ml MTBE and dried at 50 C under reduced pressure to provide 18 g of (E)-ACETYL- ISA247 as a white powder in >98% double bond isomeric purity (by NMR). iii) Hydrolysis This product was hydrolyzed to give (E) -ISA247 in 99.7% double bond isomeric purity by HPLC.
  • 2
  • [ 121584-52-9 ]
  • [ 79309-68-5 ]
  • [ 515814-02-5 ]
YieldReaction ConditionsOperation in experiment
With boron trifluoride diethyl etherate; In dichloromethane; at -70 - 0℃; for 1.5h; 2 g (1. 623 mmol, 1 equiv. ) <strong>[121584-52-9]acetyl-cyclosporin A aldehyde</strong> and 779.8 mg (3.246 mmol, 2 equiv. ) pinacol boronate obtained by the method described in Example 6, i) were dissolved in 20 ml dichloromethane. The solution was cooled to - 70 C and 1. 28 ML (10.22 mmol, 6.30 equiv. ) borontrifluoride etherate were added. After 30 min. AT-70 C, the reaction mixture was slowly warmed up to 0 C and reaction was continued for 60 min. at 0 C. 20 ML water were added. The organic phase was separated, washed with 20 ML of a 5% aqueous NAHCO3 solution, dried over MGS04, filtered and concentrated at 40 C under reduced pressure to give 2.1 g of (E) -acetyl-ISA247 in >95% double bond isomeric purity (NMR) as a white foam.
With formic acid; acetic acid; In Isopropyl acetate; at 40℃; for 15 - 20h; 40 g acetyl protected CsA-Aldehyde were charged in a feed vessel followed by 80 ml isopropyl acetate. The suspension was transferred to the reactor. The feed vessel was washed with 50 ml acetic acid which was transferred to the reactor. A clear solution was then obtained. Pinacol complex (1.25-1. 5 equiv. ) was added. The clear solution was heated to 40 C. 50 ml formic acid were added. After completion of the allylation and Peterson elimination as evidenced by HPLC analysis (after ca 15-20 hours), 246 ml isopropyl acetate were added. The reaction mixture was washed twice with 200 ml water, 300 g of 2M aqueous KOH solution (pH of the aqueous phase set between 5-8, if necessary with additional KOH solution) and 200 ml of 5% aqueous ammonium formiate. The organic phase was concentrated to ca 120 ml (Ti = ca 40 C, ca 200 mbar) and was diluted with 300 ml methanol. The organic phase was concentrated to ca 120 ml (Ti = ca 40 C, 200 mbar) and was diluted with 240 ml methanol (Ti = ca 40 C, 200 mbar). The organic phase was concentrated to ca 280 ml. 130 ml water were added over ca 60 min. at 20-25 C. The resulting white suspension was stirred 60 min. at room temperature. The solid was isolated by filtration, washed twice with 52 ml of a water/methanol mixture, dried under vacuum (T=50 C) until constant weight to provide E-acetyl-ISA247 (ca 35 g).
 

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