* 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.
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃; for 2 h; Inert atmosphere; Schlenk technique
General procedure: To a solution of trityl alcohol (0.6 mmol, 1.2 equiv.) in dry CH2Cl2 (5 mL) in a round-bottomed flask was added trifluoroacetic anhydride (0.21 mL, 1.5 mmol, 3 equiv.) at rt under argon from a Schlenk line. A deep red solution was formed immediately (with 1a, the color was slightly lighter). After stirring for 2 h, the mixture was concentrated to dryness on a rotary evaporator under reduced pressure provided by a water aspirator. The flask was reattached to the Schlenk line and flushed with argon. The intermediate trityl cation was re-dissolved in dry THF (5 mL), and added via a cannula to a solution of alcohol substrate (0.5 mmol, 1 equiv.) and DIEA (0.175 mL, 1 mmol, 2 equiv.) in dry THF (5 mL) at rt (5-8) or 0 °C (3, 9-11). After stirring for 2 h (while warming to rt slowly if applicable), the reaction mixture was poured into a separatory funnel containing 5percent NaHCO3 (15 mL), and extracted with EtOAc (10 mL×2). The extracts were dried over anhydrous Na2SO4, filtered, and concentrated.
Reference:
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3
[ 40615-36-9 ]
[ 4546-72-9 ]
[ 64325-78-6 ]
Reference:
[1] Patent: EP1253154, 2002, A1, . Location in patent: Example 2
4
[ 65-85-0 ]
[ 958-09-8 ]
[ 4546-72-9 ]
Reference:
[1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 22, p. 5045 - 5048
5
[ 64325-78-6 ]
[ 4546-72-9 ]
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6
[ 98-88-4 ]
[ 958-09-8 ]
[ 4546-72-9 ]
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[1] Chemical and Pharmaceutical Bulletin, 1981, vol. 29, # 11, p. 3274 - 3280
[2] Patent: US4667017, 1987, A,
[3] Journal of the American Chemical Society, 2010, vol. 132, # 11, p. 3862 - 3869
7
[ 958-09-8 ]
[ 4546-72-9 ]
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[1] Synthetic Communications, 2003, vol. 33, # 7, p. 1233 - 1243
[2] Nucleosides, Nucleotides and Nucleic Acids, 2002, vol. 21, # 4-5, p. 393 - 400
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8
[ 64723-02-0 ]
[ 4546-72-9 ]
Reference:
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9
[ 64911-19-9 ]
[ 4546-72-9 ]
Reference:
[1] Synthetic Communications, 2003, vol. 33, # 7, p. 1233 - 1243
[2] Journal of the American Chemical Society, 1982, vol. 104, # 5, p. 1316 - 1319
10
[ 167872-05-1 ]
[ 4546-72-9 ]
Reference:
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11
[ 961-07-9 ]
[ 4005-49-6 ]
[ 4546-72-9 ]
Reference:
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{(2R,3S,5R)-5-(6-Benzoylamino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yloxymethyl}-phosphonic acid dimethyl ester[ No CAS ]
{(2R,3S,5R)-5-(6-Benzoylamino-purin-9-yl)-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-tetrahydro-furan-2-ylmethoxymethyl}-phosphonic acid dimethyl ester[ No CAS ]
<i>N</i>-{9-[4-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(<i>tert</i>-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-9<i>H</i>-purin-6-yl}-benzamide[ No CAS ]
{(2R,3S,5R)-5-(6-Benzoylamino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yloxymethyl}-phosphonic acid 4-methoxy-1-oxy-pyridin-2-ylmethyl ester methyl ester[ No CAS ]
{(2R,3S,5R)-5-(6-Benzoylamino-purin-9-yl)-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-tetrahydro-furan-2-ylmethoxymethyl}-phosphonic acid 4-methoxy-1-oxy-pyridin-2-ylmethyl ester methyl ester[ No CAS ]
4-methoxy-1-oxy-2-pyridylmethyl 2-deoxy-3-O-(4,4'-dimethoxytrityl)-1-(6-N-benzoyladenin-9-yl)-β-D-erythro-pentofuranos-5-yloxymethylphosphonate[ No CAS ]
4-methoxy-1-oxy-2-pyridylmethyl 2-deoxy-5-O-(4,4'-dimethoxytrityl)-1-(6-N-benzoyladenin-9-yl)-β-D-erythro-pentofuranos-3-yloxymethylphosphonate[ No CAS ]
Carbonic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxy]-tetrahydro-furan-2-ylmethyl ester 3-trifluoromethyl-phenyl ester[ No CAS ]
Diisopropyl-phosphoramidous acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl ester methyl ester[ No CAS ]
N6-benzoyl-5'-O-tert-butyldimethylsilyl-3'-O-methylene-2'-deoxyadenosynyl-(3'->5')-N6-benzoyl-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thioadenosine[ No CAS ]
5'-O-dimethoxytrityl-3'-O-methylene-2'-deoxycitydylyl-(3'->5')-3'-O-methylene-5'-deoxy-5'-thiothymidylyl-(3'->5')-3'-O-tert-butyldimethylsilyl-2',5'-dideoxy-5'-thioadenosine[ No CAS ]
Acetic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-(hydroxy-{hydroxy-[2-(4-nitro-phenyl)-ethoxy]-phosphorylmethyl}-phosphinoyloxymethyl)-tetrahydro-furan-3-yl ester[ No CAS ]