Method for synthesizing 1,3,4,6-tetraacetyl-l-gulose
A tetraacetyl, gulose technology, applied in chemical instruments and methods, sugar derivatives, sugar derivatives and other directions, can solve the problems of high requirements for experimental operators, difficult to scale up production, long synthesis routes, etc., and easy to achieve conditions. Control, easy operation, short route effect
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Embodiment 1
[0035] Preparation of compound Ⅲ
[0036] 28.8g of compound II was dissolved in 130ml of dichloromethane, under the condition of ice-water bath, 16.5g of imidazole and 20.1g of TBSCl were added, stirred at room temperature for 15h, washed with water and saturated saline in sequence, dried over anhydrous sodium sulfate, and obtained a colorless viscous liquid by silica gel column chromatography , Compound III 38.1g, yield 89%.
[0037] 1 H NMR (400MHz, CDCl 3 )δ4.81(q, J=5.0Hz, 1H), 4.74(q, J=5.1Hz, 1H), 4.15(d, J= 12.6Hz, 1H), 4.00–3.92(m, 1H), 3.91– 3.84(m, 2H), 3.83–3.74(m, 2H), 3.56(d, J=8.8Hz, 1H), 3.51(s, 1H), 2.51(d, J=7.5Hz, 1H), 1.41(t , J=4.9Hz, 6H), 0.90(s, 9H), 0.08(s, 6H).
Embodiment 2
[0039] Preparation of compound Ⅳ
[0040] N 2 Under airflow, 5.2g of sodium hydride was suspended in 70ml of THF, under the condition of ice-water bath, 38.1g of compound III was dissolved in 160ml of THF and added, and 14.2ml of benzyl bromide was slowly added dropwise, and stirred at room temperature for 12h. Add water to quench the reaction, extract three times with ethyl acetate, combine the organic phases, wash with water and saturated brine successively, and dry over anhydrous sodium sulfate. Silica gel column chromatography gave 44.3 g of a white solid, compound IV, with a yield of 92%.
[0041] 1 H NMR (400MHz, CDCl 3)δ7.38–7.27(m,5H), 4.78(d,J=11.5Hz,1H),4.74(q,J=5.2Hz,1H),4.67(q,J=5.0Hz,1H),4.54( d,J=11.5Hz,1H),4.14(d,J=12.6Hz,1H),3.94(d,J=10.9Hz,1H),3.89–3.78(m,3H),3.77–3.67(m,2H ), 3.48 (s, 1H), 1.41 (d, J=5.1Hz, 3H), 1.35 (d, J=5.0Hz, 3H), 0.91 (s, 9H), 0.07 (s, 6H).
Embodiment 3
[0043] Preparation of Compound V
[0044] Compound IV 33.6g was dissolved in THF, and 39.5g TBAF·3H was added in batches 2 0, stirred at room temperature for 6 h, added water and ethyl acetate to separate the liquids, extracted the aqueous phase twice with ethyl acetate, combined with the organic phase, washed successively with saturated aqueous ammonium chloride solution and saturated brine, and dried over anhydrous sodium sulfate. Suction filtration, the filtrate was spin-dried, petroleum ether was added and stirred for 2 h, and a white solid was obtained by suction filtration, 19.9 g of compound V, with a yield of 74%.
[0045] 1 H NMR (400MHz, CDCl 3 )δ7.41–7.27(m,5H),4.79(q,J=5.1Hz,1H),4.71–4.62(m,2H),4.54(d,J=11.4Hz,1H),4.13(dd,J =12.6,0.9Hz,1H),3.91–3.80(m,3H),3.80–3.70(m,3H),3.49(s,1H),2.01(dd,J=8.9,3.1Hz,1H),1.41( d, J=5.1 Hz, 3H), 1.35 (d, J=5.1 Hz, 3H).
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