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[ CAS No. 15397-15-6 ] {[proInfo.proName]}

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Chemical Structure| 15397-15-6
Chemical Structure| 15397-15-6
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Product Details of [ 15397-15-6 ]

CAS No. :15397-15-6 MDL No. :MFCD07369658
Formula : C34H28O9 Boiling Point : -
Linear Structure Formula :- InChI Key :QJZSLTLDMBDKOU-VBHQRPIPSA-N
M.W : 580.58 Pubchem ID :10875560
Synonyms :

Safety of [ 15397-15-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 15397-15-6 ]

* 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.

  • Upstream synthesis route of [ 15397-15-6 ]
  • Downstream synthetic route of [ 15397-15-6 ]

[ 15397-15-6 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 729596-46-7 ]
  • [ 98-88-4 ]
  • [ 15397-15-6 ]
YieldReaction ConditionsOperation in experiment
70% With triethylamine In acetonitrile at 20 - 60℃; for 2 - 4 h; 100 g (0.27 moles) of 3,5-di O-benzoyl-2-C-methyl-D-ribofuranose synthesized in example 6 is added by stirring to 300 ml of acetonitrile, then 280 ml (2 moles) of triethylamine is added. 78.3 ml (0.67 moles) of benzoyl chloride is dripped at room temperature. At the end of the addition the mixture is warmed for 2 hours at 60 C., then an HPLC test is carried out.The reaction mixture is cooled to room temperature and 150 ml of water is added. The solid is filtered, washed with a mixture acetonitrile/water=2/1 and dried under vacuum up to constant weight. 109 g of product 1,2,3,5-tetra-O-benzoyl-2-C-methyl-?-D-ribofuranose is obtained. Yield=70percent.The product 3,5-di-O-benzoyl-2-C-methyl-D-ribofuranose (8.25 Kg22.2 moles) synthesized in example 23 is dissolved in 21 Kg of acetonitrile and then loaded in a 100 l reactor. 16.8 Kg (166.5 moles) of triethylamine is added and 9.8 Kg (69.7 moles) of benzoyl chloride is dripped; the temperature grows spontaneously. Then the mixture is heated at 60° C. for 4 hours. Thereafter the reaction is cooled at room temperature and 13.7 l of water is dripped. The mixture is cooled at 0° C. and is kept under stirring 1 hour. The solid is filtered and washed with 8 l of a mixture 2/1 acetonitrile/water cooled at 0° C. and then with 4.7 Kg of cold methyl alcohol.
Reference: [1] Patent: US2004/158059, 2004, A1, . Location in patent: Page 7; 9
  • 2
  • [ 30361-18-3 ]
  • [ 98-88-4 ]
  • [ 15397-15-6 ]
YieldReaction ConditionsOperation in experiment
70% With triethylamine In acetonitrile at 60℃; for 2 - 4 h; 100 g (0.27 moles) of 3,5-di O-BENZOYL-2-C-METHYL-D-RIBOFURANOSE synthesized in example 6 is added by stirring to 300 ml of acetonitrile, then 280 ml (2 moles) of triethylamine is added. 78.3 ml (0.67 moles) of benzoyl chloride is dripped at room temperature. At the end of the addition the mixture is warmed for 2 hours at 60 C, then an HPLC test is carried out. The reaction mixture is cooled to room temperature and 150 ml of water is added. The solid is filtered, washed with a mixture ACETONITRILE/WATER= 2/1 and dried under vacuum up to constant weight. 109 g of product 1, 2,3, 5-tetra-O-benzoyl-2-C-methyl-?-D-ribofuranose is obtained. Yield = 70percent. 1H-NMR (CDC13, 300 MHz): 8 ppm 7.07 (1H, s, H-1) ; 5.96 (1H, d, H-3); 4.79 (1H, m, H- 4); 4.62 (2H, system AB, CH2-5). 13C-NMR (CDC13, 300 MHz): 6 ppm 97. 97 (C-1) ; 86.82 (C-4); 78.71 (C-3); 76.31 (C-2), 64.01 (C-5).
Reference: [1] Patent: WO2004/69851, 2004, A1, . Location in patent: Page 16-17; 22
  • 3
  • [ 30361-18-3 ]
  • [ 98-88-4 ]
  • [ 15397-15-6 ]
YieldReaction ConditionsOperation in experiment
67.1% With triethylamine In dichloromethane at 15℃; for 3 h; Cooling with ice A solution of the compound A2, 64 g of benzoyl chloride and 250 mL of dichloromethane were added to the reaction flask, and the mixture was cooled in an ice bath, stirred, and 48 g of triethylamine was slowly added dropwise. After the addition was completed, the reaction was stirred at 15 ° C for 3 hours. , washing with water, concentration, crystallization, to obtain compound A3, the total yield of step two and step three is 67.1percent
Reference: [1] Patent: CN108440613, 2018, A, . Location in patent: Paragraph 0022; 0024; 0053
  • 4
  • [ 30361-17-2 ]
  • [ 98-88-4 ]
  • [ 15397-15-6 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 1, p. 17 - 22
  • 5
  • [ 492-30-8 ]
  • [ 15397-15-6 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 1, p. 17 - 22
[2] Patent: CN108440613, 2018, A,
  • 6
  • [ 98-88-4 ]
  • [ 15397-15-6 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 1, p. 17 - 22
[2] Patent: CN108440613, 2018, A,
  • 7
  • [ 7392-74-7 ]
  • [ 15397-15-6 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 1, p. 17 - 22
  • 8
  • [ 16434-48-3 ]
  • [ 30361-17-2 ]
  • [ 98-88-4 ]
  • [ 15397-15-6 ]
Reference: [1] Journal of Organic Chemistry, 1997, vol. 62, # 6, p. 1754 - 1759
[2] Journal of Organic Chemistry, 1997, vol. 62, # 6, p. 1754 - 1759
  • 9
  • [ 729596-46-7 ]
  • [ 15397-15-6 ]
Reference: [1] Patent: CN108440613, 2018, A,
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