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[ CAS No. 533-67-5 ]

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Chemical Structure| 533-67-5
Chemical Structure| 533-67-5
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Product Details of [ 533-67-5 ]

CAS No. :533-67-5 MDL No. :MFCD00135904
Formula : C5H10O4 Boiling Point : 379.7°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :134.13 g/mol Pubchem ID :5460005
Synonyms :

1. Thyminose

Safety of [ 533-67-5 ]

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 [ 533-67-5 ]

  • Upstream synthesis route of [ 533-67-5 ]
  • Downstream synthetic route of [ 533-67-5 ]

[ 533-67-5 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 533-67-5 ]
  • [ 34371-14-7 ]
YieldReaction ConditionsOperation in experiment
78% With bromine In water at 20℃; for 120 h; Example 1A
(4S,5R)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one
A 500 mL round-bottomed flask was charged with 2-deoxy-D-ribose (10 g, 74.6 mmol) and water (60 mL), followed by the dropwise addition of bromine (59.6 g, 373 mmol).
The contents were then stirred at room temperature for 5 days.
The reaction mixture was then diluted with water (300 mL) and then extracted with tert-butyl methyl ether (3*200 mL).
The aqueous layer was then neutralized with the addition of silver carbonate until the pH of the aqueous solution reached 6.
The resulting solids were removed by filtration and the filtrate was concentrated under vacuum to provide a residue which was dissolved in ethyl acetate (200 mL), followed by the addition of magnesium sulfate.
After sitting overnight, the solids were filtered off and the filtrate was concentrated to provide the title compound as an oil (7.72 g, 78percent).
1H NMR (400 MHz, CDCl3) δ 1.83 (t, J=5.9 Hz, 1H), 2.13 (d, J=4.3 Hz, 1H), 2.57 (dd, J=18.1, 4.0 Hz, 1H), 3.00 (dd, J=18.0, 7.2 Hz, 1H), 3.85 (m, 1H), 3.97 (m, 1H), 4.46 (q, J=3.2 Hz, 1H), 4.65 (m, 1H).
Reference: [1] European Journal of Organic Chemistry, 2013, # 7, p. 1306 - 1317
[2] Patent: US2017/57981, 2017, A1, . Location in patent: Paragraph 0268; 0269; 0320; 0321
[3] RSC Advances, 2014, vol. 4, # 22, p. 11023 - 11028
[4] Patent: WO2011/3018, 2011, A2, . Location in patent: Page/Page column 40-41
[5] Patent: WO2015/81297, 2015, A1, . Location in patent: Paragraph 00291
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