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[ CAS No. 76801-85-9 ]

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2D
Chemical Structure| 76801-85-9
Chemical Structure| 76801-85-9
Structure of 76801-85-9 *Storage: {[proInfo.prStorage]}

Quality Control of [ 76801-85-9 ]

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Related Doc. of [ 76801-85-9 ]

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Product Details of [ 76801-85-9 ]

CAS No. :76801-85-9MDL No. :MFCD09038719
Formula :C37H70N2O12Boiling Point :815.2°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :734.96Pubchem ID :-
Synonyms :

1. Azathramycin

Computed Properties of [ 76801-85-9 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 76801-85-9 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 76801-85-9 ]

  • Upstream synthesis route of [ 76801-85-9 ]
  • Downstream synthetic route of [ 76801-85-9 ]

[ 76801-85-9 ] Synthesis Path-Upstream   1~8

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YieldReaction ConditionsOperation in experiment
85%
Stage #1: With hydrogen; acetic acid In methanol at 40 - 45℃;
Stage #2: With sodium hydroxide In water
Example-2; [93][94] Preparation of 9-deoxo-9a-aza-9a-homoerythromycin A; [95][96] To a mixture of 6,9-imino ether (II) (70.Og) in methanol (700ml) was added acetic acid till pH 5 to 6 is obtained. PtO2 (7.Og) in water was added to the above mixture and reduced under hydrogenation condition at hydrogen pressure 8 to 9 kg at 4O0C to 450C for about 4 to 5 hours. After completion of the reaction the reaction mixture was filtered through hyflobed, washed with methanol. The combined filtrate was distilled under vacuum to evaporate methanol. D. M. water (700ml) was added to the remaining filtrate. The pH of the solution was adjusted to 11 to 12 using aq. Sodium hydroxide solution. The solid precipitated was filtered, suck dried and then dried in oven to give 9-deoxo-9a-aza-9a-homo erythromycin A (III) (55.0g).[97] Yield: 85percent
84.4%
Stage #1: Heating
Stage #2: at 8℃;
50 g of erythromycin A-9 oxime was added to a 500 ml three-necked flask equipped with stirring,Followed by adding 200 ml of purified water,12.0 g sodium bicarbonate, the reaction temperature is controlled at about 5 ,Add another 15mlMethylsulfonyl chloride,With the addition of methyl sulfonyl chloride reaction solution gradually thinning,Until fully clarified,After the incubation reaction for 2 ~ 3 hr,A solution of 5.0percent sodium borohydride in 100 ml,While 36percent acetic acid solution was added dropwise,Control the pH between 6 to 8,2 to 6 hours drop finished,After heating for 1 to 2 hours,Add 15g of gulonic acid,Hydrolysis temperature control at about 8 ,With 10percent hydrochloric acid pH1.5 ~ 2.5,Hydrolysis 8min, adding 100ml acetone,Plus 30percent of the liquid alkali pH 10 ~ 11,With the addition of crystals to the liquid caustic soda,Cooling to 0 ~ 10 , filtration,Dried up azithromycin42.2 g (yield 84.4percent).
70.3% at 0 - 20℃; for 24.00 h; Under 0 ° C ice bath conditions,0.1 g b (0.1435 mmol),0.088 g sodium borohydride (2.333 mmol)Dissolved in 1.2ml of anhydrous methanol,Stirring reaction 4h, then remove the ice bath,Continue to react at room temperature for 20h,After the reaction is completed, carbon dioxide is introduced into a white solid to form,Filtered, the filter cake was washed with a small amount of methanol, distilled under reduced pressure methanol, a white solid.DCM was added to dissolve the white solid,The organic phase is washed twice with 10percent sodium bicarbonate, the layers are separated and the organic phase is added with 100 ml of water and the pH is adjusted to 2-3 (preferably 2.5) with 1 mol / L hydrochloric acid under stirring.After stirring for 20 minutes, the pH is adjusted to 6-7 (preferably 6.5) with 10percent sodium hydroxide and the organic layer discarded.The aqueous layer was added with 20 ml of DCM, the pH was adjusted to 11 with 10percent sodium hydroxide, stirred for 15 minutes, separated to give a DCM solvent,Drying in vacuo gave a white solid (III-1) (see Figure 1) in a yield of 70.6percent
Reference: [1] Patent: WO2009/156938, 2009, A2. Location in patent: Page/Page column 8
[2] Patent: CN106632543, 2017, A. Location in patent: Paragraph 0003; 0025-0026
[3] Organic and Biomolecular Chemistry, 2008, vol. 6, # 22, p. 4120 - 4124
[4] Patent: CN106478541, 2017, A. Location in patent: Paragraph 0022; 0047
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YieldReaction ConditionsOperation in experiment
57.4 g
Stage #1: With sodium hydroxide In dichloromethane at 10℃;
Stage #2: With sodium tetrahydroborate In dichloromethane at 10℃;
85g of erythromycin A 9-oxime thiocyanate, 500ml of dichloromethane was added to 1000ml reaction flask then adjust PH9 ~ 11 by adding 20percent sodium hydroxide and after all the solid was dissolved the stratification was carried out . the upper aqueous layer was again extracted with dichloromethane and the combined the dichloromethane layers. Dichloromethane was concentrated by evaporation and 250ml of water was added. cooled to below 10 ° C, then methanesulfonyl chloride 25g was added and the incubation reaction was carried out until erythromycin A9-oxime was complete. With 20percent sodium hydroxide adjusted pH3 ~ 7, cooling to below 10 ° C, sodium borohydride 7g was added and Insulation reaction is completed. Then dichloromethane 1000ml was added , adjust pH0. 5 ~ 2. 5 with 10percent hydrochloric acid , incubation at 0 ~ 10 ° C and stirred for 20 minutes. Then, adjusted pH9 ~ 11 by adding 20percent sodium hydroxide, allowed to stand to separate the layers and the aqueous layer was extracted with 100ml of dichloromethane then the combined dichloromethane layer and 200ml of water was added. Concentrated under reduced pressure to remove dichloromethane, cooled to 0 ~ 5 ° C, washed the filter and drying was carried out to obtain 57. 4g products, purity 94.6percent by HPLC , moisture
Reference: [1] Patent: CN103772456, 2016, B. Location in patent: Paragraph 0029-0030
[2] Patent: CN107141324, 2017, A
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Reference: [1] Patent: WO2007/80507, 2007, A2. Location in patent: Page/Page column 11
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  • [ 111321-02-9 ]
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Reference: [1] Tetrahedron Letters, 2000, vol. 41, # 18, p. 3371 - 3375
[2] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 13, p. 4498 - 4510
[3] Journal of Medicinal Chemistry, 2011, vol. 54, # 8, p. 2792 - 2804
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  • [ 13127-18-9 ]
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Reference: [1] Chemical Communications, 2018, vol. 54, # 6, p. 654 - 657
[2] Patent: CN106478541, 2017, A
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Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 8, p. 2792 - 2804
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Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 8, p. 2792 - 2804
[2] Patent: CN106478541, 2017, A
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  • [ 7704-67-8 ]
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Reference: [1] Patent: CN107141324, 2017, A
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