Technology Process of 2-[(2R,3S,4aR,5S,7S,8aR,9aS,10aS)-5-Benzyloxy-7-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-4a,10a-dimethyl-decahydro-1,8,10-trioxa-anthracen-2-yl]-ethanol
There total 11 articles about 2-[(2R,3S,4aR,5S,7S,8aR,9aS,10aS)-5-Benzyloxy-7-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-4a,10a-dimethyl-decahydro-1,8,10-trioxa-anthracen-2-yl]-ethanol which
guide to synthetic route it.
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synthetic route:
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![[(2R,3S,4aR,5S,7S,8aR,9aS,10aS)-5-Benzyloxy-7-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-4a,10a-dimethyl-decahydro-1,8,10-trioxa-anthracen-2-yl]-acetic acid ethyl ester](/Databaselist/images/loading.webp)
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[(2R,3S,4aR,5S,7S,8aR,9aS,10aS)-5-Benzyloxy-7-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-4a,10a-dimethyl-decahydro-1,8,10-trioxa-anthracen-2-yl]-acetic acid ethyl ester
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494760-72-4
2-[(2R,3S,4aR,5S,7S,8aR,9aS,10aS)-5-Benzyloxy-7-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-4a,10a-dimethyl-decahydro-1,8,10-trioxa-anthracen-2-yl]-ethanol
- Guidance literature:
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With
lithium aluminium tetrahydride;
In
diethyl ether;
at 0 ℃;
for 0.666667h;
DOI:10.1021/ja036984k
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494760-72-4
2-[(2R,3S,4aR,5S,7S,8aR,9aS,10aS)-5-Benzyloxy-7-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-4a,10a-dimethyl-decahydro-1,8,10-trioxa-anthracen-2-yl]-ethanol
- Guidance literature:
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Multi-step reaction with 9 steps
1.1: cyclohexene; BH3*SMe2 / tetrahydrofuran / 1 h / 0 °C
1.2: 95 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 1 h / 0 °C
2.1: aq. KBr; TEMPO; NaClO / NaHCO3 / CH2Cl2 / 1 h / 0 °C
3.1: BF3*OEt3 / CH2Cl2 / -78 - 0 °C
4.1: 2.58 g / TBAF / tetrahydrofuran / 10 h / Heating
5.1: 94 percent / N-methylmorpholine / CH2Cl2 / 12 h / 20 °C
6.1: 94 percent / NaHCO3; MeI; H2O / acetonitrile / 2.5 h / 50 °C
7.1: 98 percent / SmI2; MeOH / tetrahydrofuran / 0.33 h / 0 °C
8.1: 2,6-lutidine / CH2Cl2 / 2 h / 0 °C
9.1: 695 mg / LiAlH4 / diethyl ether / 0.67 h / 0 °C
With
4-methyl-morpholine; 2,6-dimethylpyridine; methanol; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; lithium aluminium tetrahydride; samarium diiodide; dimethylsulfide borane complex; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; sodium hydrogencarbonate; potassium bromide; cyclohexene; methyl iodide;
sodium hydrogencarbonate;
In
tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;
7.1: Nakata reaction;
DOI:10.1021/ja036984k
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494760-72-4
2-[(2R,3S,4aR,5S,7S,8aR,9aS,10aS)-5-Benzyloxy-7-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-4a,10a-dimethyl-decahydro-1,8,10-trioxa-anthracen-2-yl]-ethanol
- Guidance literature:
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Multi-step reaction with 8 steps
1: aq. KBr; TEMPO; NaClO / NaHCO3 / CH2Cl2 / 1 h / 0 °C
2: BF3*OEt3 / CH2Cl2 / -78 - 0 °C
3: 2.58 g / TBAF / tetrahydrofuran / 10 h / Heating
4: 94 percent / N-methylmorpholine / CH2Cl2 / 12 h / 20 °C
5: 94 percent / NaHCO3; MeI; H2O / acetonitrile / 2.5 h / 50 °C
6: 98 percent / SmI2; MeOH / tetrahydrofuran / 0.33 h / 0 °C
7: 2,6-lutidine / CH2Cl2 / 2 h / 0 °C
8: 695 mg / LiAlH4 / diethyl ether / 0.67 h / 0 °C
With
4-methyl-morpholine; 2,6-dimethylpyridine; methanol; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; lithium aluminium tetrahydride; samarium diiodide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; sodium hydrogencarbonate; potassium bromide; methyl iodide;
sodium hydrogencarbonate;
In
tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;
6: Nakata reaction;
DOI:10.1021/ja036984k
