Technology Process of Benzoic acid (R)-2-benzyloxy-1-{6-[(2R,4R,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-1,5,9,10-tetramethoxy-anthracen-2-yl}-2-methyl-pent-4-enyl ester
There total 30 articles about Benzoic acid (R)-2-benzyloxy-1-{6-[(2R,4R,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yl]-1,5,9,10-tetramethoxy-anthracen-2-yl}-2-methyl-pent-4-enyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 10 steps
1: 100 percent / (i-Pr)2NEt / CH2Cl2 / Ambient temperature
2: H2 / 10percent Pd/C / dimethylformamide / 0.25 h / 760 Torr / Ambient temperature
3: 1.) NaH / 1.) DMF, RT, 15 min, 2.) DMF, RT, 20 min
4: 92.3 percent / EtSH, BF3*OEt2 / CH2Cl2 / 1.) -78 deg C, 20 min, 2.) from -78 deg C to -20 deg C , 30 min
5: 85.5 percent / Cp2HfCl2, AgClO4, molecular sieves 4A / CH2Cl2 / 0.83 h / -78 - 0 °C
6: 100 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature
7: 96.2 percent / 3 N aq. NaOH / methanol / Ambient temperature
8: 96.4 percent / 2,6-lutidine / CH2Cl2 / 2 h / Ambient temperature
10: 4-(dimethylamino)pyridine (4-DMAP), pyridine / Ambient temperature
With
pyridine; 2,6-dimethylpyridine; dmap; sodium hydroxide; bis(cyclopentadienyl)hafnium dichloride; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; silver perchlorate; sodium hydride; N-ethyl-N,N-diisopropylamine; ethanethiol;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00018a041
- Guidance literature:
-
Multi-step reaction with 10 steps
1: 100 percent / (i-Pr)2NEt / CH2Cl2 / Ambient temperature
2: H2 / 10percent Pd/C / dimethylformamide / 0.25 h / 760 Torr / Ambient temperature
3: 1.) NaH / 1.) DMF, RT, 15 min, 2.) DMF, RT, 20 min
4: 92.3 percent / EtSH, BF3*OEt2 / CH2Cl2 / 1.) -78 deg C, 20 min, 2.) from -78 deg C to -20 deg C , 30 min
5: 85.5 percent / Cp2HfCl2, AgClO4, molecular sieves 4A / CH2Cl2 / 0.83 h / -78 - 0 °C
6: 100 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature
7: 96.2 percent / 3 N aq. NaOH / methanol / Ambient temperature
8: 96.4 percent / 2,6-lutidine / CH2Cl2 / 2 h / Ambient temperature
10: 4-(dimethylamino)pyridine (4-DMAP), pyridine / Ambient temperature
With
pyridine; 2,6-dimethylpyridine; dmap; sodium hydroxide; bis(cyclopentadienyl)hafnium dichloride; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; silver perchlorate; sodium hydride; N-ethyl-N,N-diisopropylamine; ethanethiol;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00018a041
- Guidance literature:
-
Multi-step reaction with 9 steps
1: H2 / 10percent Pd/C / dimethylformamide / 0.25 h / 760 Torr / Ambient temperature
2: 1.) NaH / 1.) DMF, RT, 15 min, 2.) DMF, RT, 20 min
3: 92.3 percent / EtSH, BF3*OEt2 / CH2Cl2 / 1.) -78 deg C, 20 min, 2.) from -78 deg C to -20 deg C , 30 min
4: 85.5 percent / Cp2HfCl2, AgClO4, molecular sieves 4A / CH2Cl2 / 0.83 h / -78 - 0 °C
5: 100 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature
6: 96.2 percent / 3 N aq. NaOH / methanol / Ambient temperature
7: 96.4 percent / 2,6-lutidine / CH2Cl2 / 2 h / Ambient temperature
9: 4-(dimethylamino)pyridine (4-DMAP), pyridine / Ambient temperature
With
pyridine; 2,6-dimethylpyridine; dmap; sodium hydroxide; bis(cyclopentadienyl)hafnium dichloride; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; silver perchlorate; sodium hydride; ethanethiol;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00018a041
