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[ CAS No. 34408-14-5 ] {[proInfo.proName]}

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Chemical Structure| 34408-14-5
Chemical Structure| 34408-14-5
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Product Details of [ 34408-14-5 ]

CAS No. :34408-14-5 MDL No. :MFCD01076457
Formula : C10H12ClN5O4 Boiling Point : -
Linear Structure Formula :- InChI Key :MHDPPLULTMGBSI-UUOKFMHZSA-N
M.W : 301.69 Pubchem ID :147569
Synonyms :
8-Cl-Ado

Safety of [ 34408-14-5 ]

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 [ 34408-14-5 ]

* 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.

  • Upstream synthesis route of [ 34408-14-5 ]
  • Downstream synthetic route of [ 34408-14-5 ]

[ 34408-14-5 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 58-61-7 ]
  • [ 34408-14-5 ]
YieldReaction ConditionsOperation in experiment
52% With N-chloro-succinimide; acetic acid In N,N-dimethyl-formamide at 20℃; for 48 h; Procedure 2: Adenosine (1.09g, 4.08 mmol) was suspended in DMF (50 mL) and glacial acetic acid (10 mL) was added. A solution of N-chlorosuccinimide (2 g, 15 mmol) in DMF (15 mL) was added dropwise. The reaction mixture was stirred at rt for 48 hours and the volatiles were evaporated in vacuo to give yellow gum. The crude was absorbed on silica and purified by silica gel CC (packed in 5percent MeOHICHC13, eluted with 7percent MeOHICHC13) to yield a white powder (0.65 g, 52 percent).‘H NIVIR (500 MHz, DMSO-d6) 8.16 (s, 1H, H-2), 7.55 (br s, 2H, NH2), 5.86 (d, J = 6.8 Hz, 1H, Hi’), 5.48 (d, J 6.2 Hz, iH, 2’OH), 5.45 (d, J 4.0 Hz, iH, 5’-OH), 5.23 (d, J4.6 Hz, iH, 3’OH), 5.08-5.06 (m, iH, H-2’), 4.23-4.i8 (m, iH, H3’), 4.01-3.96 (m, iH, H4’),3.72-3.65 (m, iH, H5’), 3.57-3.50 (m, iH, H5’).
Reference: [1] Patent: WO2017/207989, 2017, A1, . Location in patent: Page/Page column 55; 56
[2] Journal of Organic Chemistry, 1981, vol. 46, # 13, p. 2819 - 2823
[3] Nucleosides, nucleotides and nucleic acids, 2002, vol. 21, # 8-9, p. 599 - 617
  • 2
  • [ 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
  • 3
  • [ 7732-18-5 ]
  • [ 58-61-7 ]
  • [ 34408-14-5 ]
YieldReaction ConditionsOperation in experiment
65% With acetic acid In methanol; N,N-dimethyl-formamide Method B
to a solution of adenosine (1.09 g, 4.1 mmol) in DMF (50 mL) and AcOH (10 mL) was added N-Chlorosuccinamide (NCS, 2.0 g, 15 mmol).
The reaction mixture was stirred at room temperature for 6 days.
The solvents were evaporated to dryness and the residue was purified by HPLC on a C-18 reverse phase column using MeOH:AcOH:H2 O (18:1:18, v/v) to give 0.8 g (65percent) of 2, which was identical to the title compound prepared by Method A.
Reference: [1] Patent: US4861873, 1989, A,
  • 4
  • [ 3001-45-4 ]
  • [ 34408-14-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 15, p. 6248 - 6263
  • 5
  • [ 2946-39-6 ]
  • [ 34408-14-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 15, p. 6248 - 6263
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