Hydrogen Peroxide → (1S,2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(4-chloro-2-(4-ethylbenzyl)phenoxy)cyclohexanol

温度

0 °C

To a stirred 0° C. THF solution of ((1S,2S,3R,6R)-4-(benzyloxymethyl)-6-(4-chloro-2-(4-ethylbenzyl)phenoxy)cyclohex-4-ene-1,2,3-triyl)tris(oxy)tris(methylene)tribenzene (27, 150 mg, 0.196 mmol) was added dropwise BH3OEt2 (2M, 0.98 mL, 1.962 mmol). After stirring for 2 h at 0° C., the mixture was warmed to 25° C. and stirred overnight. H2O2 (30%, 4.2 mL) was added, followed by added aqueous NaOH solution (1M, 3.93 mL, 3.93 mmol) to the reaction mixture at 0° C. After complete addition, the reaction mixture was warmed to 25° C. and stirred for 3 h. The reaction was quenched by addition of dilute HCl (1N, 10 mL) and extracted with ethyl acetate (3×30 mL). The organic layers were washed with water and brine prior to drying over anhydrous Na2SO4. The residue was purified by preparative TLC (EA:PE=1:8 v/v) to obtain 59 mg of (1S,2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(4-chloro-2-(4-ethylbenzyl)phenoxy)cyclohexanol (28).

1. customTo a stirred 0° C
2. temperaturethe mixture was warmed to 25° C.
3. stirringstirred overnight
4. additionAfter complete addition
5. temperaturethe reaction mixture was warmed to 25° C.
6. stirringstirred for 3 h
7. customThe reaction was quenched by addition of dilute HCl (1N, 10 mL)
8. extractionextracted with ethyl acetate (3×30 mL)
9. washThe organic layers were washed with water and brine
10. dry with materialto drying over anhydrous Na2SO4
11. customThe residue was purified by preparative TLC (EA:PE=1:8 v/v)

ORDレコード

ord-59a5452ffdba466494a8ac4a7752a089

出典データセット

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08129434B2