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Chemical Structure| 4294-16-0
Chemical Structure| 4294-16-0
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Product Details of [ 4294-16-0 ]

CAS No. :4294-16-0 MDL No. :MFCD00005740
Formula : C17H19N5O4 Boiling Point : -
Linear Structure Formula :- InChI Key :MRPKNNSABYPGBF-LSCFUAHRSA-N
M.W : 357.36 Pubchem ID :92208
Synonyms :
Benzyladenosine;DNPH1i;BAPR

Safety of [ 4294-16-0 ]

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

Application In Synthesis of [ 4294-16-0 ]

* 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 [ 4294-16-0 ]
  • Downstream synthetic route of [ 4294-16-0 ]

[ 4294-16-0 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 4294-16-0 ]
  • [ 1214-39-7 ]
Reference: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 12, p. 2156 - 2163
  • 2
  • [ 4294-16-0 ]
  • [ 1214-39-7 ]
  • [ 18646-11-2 ]
Reference: [1] Synthesis, 2011, # 15, p. 2483 - 2489
[2] Synthesis, 2011, # 15, p. 2483 - 2489
  • 3
  • [ 4294-16-0 ]
  • [ 1427459-39-9 ]
  • [ 2946-39-6 ]
YieldReaction ConditionsOperation in experiment
22% With bromine; sodium acetate; acetic acid In water at 45℃; for 2.5 h; 6-Benzylamino-9-(β-D-ribofuranosyl)purine (469.4 mg; 1.313 mmol) was suspended in 15 ml 1 M AcONa and 15 ml 1 M AcOH. Bromine water (12.7 ml) was added to suspension and mixture was heated for 2.5 h at 45° C.
Excess bromine was eliminated by addition of solid NaHSO3 and then the mixture was neutralized by 10percent NaOH and evaporated.
Residue was shaken out with water and chloroform.
Organic layer was separated, dried in MgSO4 and after filtration of desiccant evaporated to dryness.
The residue was purified by column chromatography in CHCl3-MeOH-NH4OH (95:5:0.5).
Yield 126.5 mg 6-benzylamino-8-bromo-9-(β-D-ribofuranosyl)purine (22percent), 42.2 mg starting material (9percent), 205 mg 8-bromoadenosine (45percent) and mixture of benzaldehyde and bromobenzaldehyde. Crystallization from CHCl3-hexan; mp: 98-100° C. MS ESI+: 436.2 [M+H+]. For C17H13BrN5O4 calculated 435.0542, found 436.0680 [M+H+]. 1H NMR (400 MHz; CDCl3) δ 3.75 (dd, J=2.7 Hz, 12.7 Hz, H5′), 3.90 (dd, J=2.4 Hz, 12.7 Hz, H5′), 4.20 (d, J=1.8 Hz, H4′), 4.39 (dd, J=1.8 Hz, 5.3 Hz, H3′), 4.81 (bs, —CH2—), 5.08 (dd, J=5.3 Hz, 7.2 Hz, H2′), 6.07 (d, J=7.2 Hz, H1′), 7.24 (m, H4-Ph), 7.31 (m, H3-Ph), 7.38 (m, H2-Ph), 8.19 (s, H2). MS ESI+ (8-bromoadenosine): 346.3 [M+H+]. GC: Rt (benzaldehyde)=321 s. MS EI (benzyldehyde): 105 (100percent), 77 (25percent). Rt (bromobenzyldehyde)=722 s. MS EI: 185 (100percent), 155 (50percent), 77 (45percent).
Reference: [1] Patent: US2013/72506, 2013, A1, . Location in patent: Paragraph 0128
  • 4
  • [ 4294-16-0 ]
  • [ 34408-14-5 ]
  • [ 1427459-38-8 ]
YieldReaction ConditionsOperation in experiment
20% With N-chloro-succinimide In N,N-dimethyl-formamide at 45℃; for 18 h; 6-Benzylamino-9-(β-D-ribofuranosyl)purine (115 mg, 0.322 mmol) and 51.6 mg (0.386 mmol) N-chlorosuccinimide was dissolved in 3 ml DMF and the solution was heated at 45° C. for 18 h.
The mixture was evaporated and residue was purified by column chromatography in CHCl3-MeOH-NH4OH (95:5:0.5).
Yield 25.2 mg 6-benzylamino-8-chloro-9-(β-D-ribofuranosyl)purine (20percent) a 62.1 mg starting compound (54percent); mp=90-92° C. MS ESI+: 392.2 [M+H+].
For C17H18ClN5O4 calculated 391.1047, found 392.1119 [M+H+].
1H NMR (300 MHz; CDCl3) δ 3.61 (dd, J=4.1 Hz, 8.2 Hz, H5'), 3.89 (d, J=12.7 Hz, H5'), 4.27 (s, H4'), 4.45 (d, J=5.7 Hz, H3'), 4.74 (bs, -CH2-), 4.79 (bs, -CH2-), 5.00 (dd, J=5.7 Hz, 6.3 Hz, H2'), 6.01 (d, J=7.3 Hz, H1'), 6.38 (bs, H-N), 7.28 (m, H-Ph), 8.21 (s, H2).
8-Chloroadenosine was isolated as an analytical sample for MS ESI by wash out from TLC. MS ESI+: 302.3 [M+H+].
Reference: [1] Patent: US2013/72506, 2013, A1, . Location in patent: Paragraph 0127
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