4090-55-5, The chemical industry reduces the impact on the environment during synthesis 4090-55-5, name is 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide, I believe this compound will play a more active role in future production and life.
To a stirred solution of S2 (0.84 g, 1.50 mmol) in THF (5 mL) at rt, 60%NaH (0.24 g, 6.0 mmol) was added and stirred for 30 min. Then 2,2-dimethyltrimethylene phosphorochloridate (0.39 g, 2.2 mmol) was added in one portion. After stirring for 9 hours at rt, the reaction was quenched by saturated aqueous NaHCO3 and extracted with EtOAc. The organic layer was washed with water and brine and dried over MgSO4. After filtration, the reaction mixture was concentrated in vacuo and the crude product was purified by column chromatography to give 1c as colorless foam in 85% yield (0.90 g, 1.3 mmol). 4-Fluorophenyl 3,4,6-tri-O-benzyl-2-O-(2,2-dimethyltrimethylenephosphornoyl)-1-thio-alpha-D-mannopyranoside (1c). TLC (hexane/EtOAc 5:3):Rf 0.50. [alpha]D = +76.8 (c = 1.1, CHCl3). 1H NMR (CDCl3, 600 MHz) 7.45 (dd, J= 9.0, 5.4 Hz, 2 H), 7.41 – 7.40 (m, 2 H), 7.35 – 7.27 (m, 11 H), 7.25 – 7.23 (m, 2H), 6.94 (pseudo-t, J = 9.0 Hz, 2 H), 5.59 (d, J = 1.8 Hz, 1 H), 5.11 (dt, J = 7.8,2.4 Hz), 4.91 (d, J = 10.8 Hz, 1 H), 4.82 (d, J = 11.4 Hz, 1 H), 4.63 (d, J = 11.4Hz, 1 H), 4.62 (d, J = 11.4 Hz, 1 H), 4.59 (d, J = 10.8 Hz, 1 H), 4.48 (d, J = 12.0Hz, 1 H), 4.33 (ddd, J = 5.4, 4.2, 3.0 Hz, 1 H), 4.14 (d, J = 10.8 Hz, 1 H), 4.09 (d,J = 10.8 Hz, 1 H), 3.96 (pseudo-t, J = 9.6 Hz, 1 H), 3.91 – 3.85 (m, 2 H), 3.76(ddd, J = 21.6, 10.8, 3.0 Hz, 1 H) 3.75 (dd, J = 10.8, 3.0 Hz, 1 H) 3.67 (ddd, J =22.2, 11.4, 3.0 Hz, 1 H), 1.22 (s, 3 H), 0.63 (s, 3 H). 13C NMR (CDCl3, 150 MHz) 162.8 (d, J = 246.9 Hz), 138.2, 138.0, 137.4, 134.9 (d, J = 8.1 Hz), 128.5,128.4, 128.36, 128.34, 128.2 (d, J = 3.3 Hz), 128.1, 128.0, 127.9, 127.6, 116.2 (d,J = 21.9 Hz), 87.4, 79.1, 78.39, 78.35, 78.30, 78.25, 78.1, 75.2, 74.4, 74.3, 74.1,73.4, 72.6, 71.9, 69.0, 32.0, 21.8, 20.1. HRMS (ESI) m/z calcd for C38H42FNNaO8PS [M+Na]+, 731.2214; found, 731.2223.
The chemical industry reduces the impact on the environment during synthesis 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide. I believe this compound will play a more active role in future production and life.
Reference:
Article; Manmode, Sujit; Sato, Takumi; Sasaki, Norihiko; Notsu, Ikumi; Hayase, Shuichi; Nokami, Toshiki; Itoh, Toshiyuki; Carbohydrate Research; vol. 450; (2017); p. 44 – 48;,
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