6065-82-3, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 6065-82-3 as follows.
TMSOTf (55.2 muL, 305 mumol) was added to a suspension of 23 (31.8 mg, 50.8 mumol) and ethyl diethoxyacetate (27.3 muL, 152 mumol) in dichloroethane (2 mL), and the reaction mixture was heated at 100 C for 21.5 h. As a large amount of starting material still remained at this stage, TMSOTf (18.2 muL, 102 mumol) and ethyl diethoxyacetate (9.1 muL, 50.8 mumol) were added to the reaction mixture and the whole was heated at 100 C for 20.5 h. The reaction mixture was diluted with saturated NaHCO3 (10 mL) and extracted with chloroform (3¡Á30 mL). The combined extracts were washed with brine (30 mL), dried, and concentrated in vacuo to give a residue (60 mg). Chromatography of this residue on a silica gel (10 g) column with chloroform-methanol (100/1) gave 26a (16.1 mg, 46%) as a pale yellow oil. IR (KBr) 3375, 2927, 2854, 1734, 1645, 1460, 1178, 1058 cm-1; 1H NMR (CDCl3, 500 MHz) delta 1.289 (3H, t, J=7.2 Hz, OCH2CH3), 1.86 (3H, s, 12-CH3), 2.11 (3H, s, 3-CH3), 2.26 (1H, dd, J=17.1, 10.7 Hz, 14-Hbeta), 2.50 (3H, s, TsCH3), 2.55 (3H, s, NCH3), 2.78 (1H, d, J=17.4 Hz, 5-Hbeta), 2.97 (1H, dd, J=17.4, 7.6 Hz, 5-Halpha), 3.26 (1H, dd, J=17.1, 4.2 Hz, 14-Halpha), 3.69 (3H, s, 2-OCH3), 3.74 (3H, s, 11-OCH3), 3.83 (3H, s, 10-OCH3), 3.87 (3H, s, 1-OCH3), 3.86-3.90 (1H, overlapped, 6-H), 4.23 (2H, q, J=7.0 Hz, OCH2CH3), 4.24-4.29 (1H, m, 14a-H), 4.31 (1H, br s, 15-H), 4.70 (1H, br s, OH), 6.34 (1H, s, 9-H), 7.38 (2H, d, J=8.2 Hz, 2¡Á2′-H), 7.86 (2H, d, J=8.2 Hz, 2¡Á3′-H); 13C NMR (CDCl3, 125 Hz) delta 8.7 (3-CH3), 10.8 (12-CH3), 14.2 (OCH2CH3), 21.4 (TsCH3), 23.6 (C5), 26.5 (C14), 40.4 (NCH3), 51.2 (C9), 52.4 (C14a), 54.2 (C15), 58.6 (C6), 59.9 (10-OCH3), 60.0 (2-OCH3), 60.3 (1-OCH3), 60.6 (11-OCH3), 61.7 (OCH2CH3), 114.3 (C4a), 117.3 (C3), 122.4 (C9a), 123.0 (C15a), 125.0 (C13a), 127.1 (C12), 128.6 (2¡ÁCH), 129.7 (2¡ÁCH), 133.6 (C1′), 141.0 (C13), 144.7 (C1), 145.3 (C4′), 147.8 (C4), 148.9 (C10), 149.3 (C2), 149.6 (C11), 169.8 (C7), 171.4 (C16); FABMS m/z 711 [M+1]+; HRFABMS m/z 711.2585 (M++1, calcd for C36H43N2O11S, 711.2588).
According to the analysis of related databases, Ethyl diethoxyacetate, the application of this compound in the production field has become more and more popular.
Reference:
Article; Yokoya, Masashi; Shinada-Fujino, Kimiko; Yoshida, Saiko; Mimura, Masahiro; Takada, Hiroki; Saito, Naoki; Tetrahedron; vol. 68; 22; (2012); p. 4166 – 4181;,
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