Technology Process of (4S,15aS)-4-((1S,2R)-1,2-Bis-benzyloxy-heptyl)-8-(toluene-4-sulfonyl)-1,4,6,7,8,9,10,11,12,13,15,15a-dodecahydro-5H-4a,8,13-triaza-benzocyclotridecen-14-one
There total 24 articles about (4S,15aS)-4-((1S,2R)-1,2-Bis-benzyloxy-heptyl)-8-(toluene-4-sulfonyl)-1,4,6,7,8,9,10,11,12,13,15,15a-dodecahydro-5H-4a,8,13-triaza-benzocyclotridecen-14-one which
guide to synthetic route it.
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synthetic route:
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135091-08-6
(4S,15aS)-4-((1S,2R)-1,2-Bis-benzyloxy-heptyl)-8-(toluene-4-sulfonyl)-1,4,6,7,8,9,10,11,12,13,15,15a-dodecahydro-5H-4a,8,13-triaza-benzocyclotridecen-14-one
- Guidance literature:
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With
dmap; 2-chloro-1-methyl-pyridinium iodide;
In
dichloromethane;
Yield given;
DOI:10.1016/S0040-4039(00)74295-X
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135091-08-6
(4S,15aS)-4-((1S,2R)-1,2-Bis-benzyloxy-heptyl)-8-(toluene-4-sulfonyl)-1,4,6,7,8,9,10,11,12,13,15,15a-dodecahydro-5H-4a,8,13-triaza-benzocyclotridecen-14-one
- Guidance literature:
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Multi-step reaction with 22 steps
2: (COCl)2, N(C2H5)3 / dimethylsulfoxide; CH2Cl2
3: NaH / diethyl ether
4: 90 percent / DIBAH / CH2Cl2
5: PDC / dimethylformamide
6: tetrahydrofuran
7: 81 percent / 144 h / 40 °C
8: 92 percent / LAH / diethyl ether
9: (COCl)2, N(C2H5)3 / dimethylsulfoxide; CH2Cl2 / -60 °C
10: tetrahydrofuran
11: 93 percent / CSA
12: 86 percent / Na, C10H8 / tetrahydrofuran
13: 94 percent / K2CO3 / benzene; toluene; H2O
14: 94 percent / LAH / tetrahydrofuran / Heating
15: 95 percent / K2CO3 / dimethylformamide
16: NH2NH2 / ethanol
17: CH2Cl2
18: TsOH/acetone
19: K2CO3/MeOH
20: 1.) NaOCl2 / 1.) 2-methyl-2-butene, t-BuOH, 2.) Et2O
21: Ba(OH)2 / methanol; H2O
22: 2-chloro-1-methylpyridinium iodide, DMAP / CH2Cl2
With
methanol; dmap; barium dihydroxide; lithium aluminium tetrahydride; dipyridinium dichromate; oxalyl dichloride; naphthalene; camphor-10-sulfonic acid; 2-chloro-1-methyl-pyridinium iodide; sodium; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; acetone; hydrazine;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1016/S0040-4039(00)74295-X
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135091-08-6
(4S,15aS)-4-((1S,2R)-1,2-Bis-benzyloxy-heptyl)-8-(toluene-4-sulfonyl)-1,4,6,7,8,9,10,11,12,13,15,15a-dodecahydro-5H-4a,8,13-triaza-benzocyclotridecen-14-one
- Guidance literature:
-
Multi-step reaction with 22 steps
2: (COCl)2, N(C2H5)3 / dimethylsulfoxide; CH2Cl2
3: NaH / diethyl ether
4: 90 percent / DIBAH / CH2Cl2
5: PDC / dimethylformamide
6: tetrahydrofuran
7: 81 percent / 144 h / 40 °C
8: 92 percent / LAH / diethyl ether
9: (COCl)2, N(C2H5)3 / dimethylsulfoxide; CH2Cl2 / -60 °C
10: tetrahydrofuran
11: 93 percent / CSA
12: 86 percent / Na, C10H8 / tetrahydrofuran
13: 94 percent / K2CO3 / benzene; toluene; H2O
14: 94 percent / LAH / tetrahydrofuran / Heating
15: 95 percent / K2CO3 / dimethylformamide
16: NH2NH2 / ethanol
17: CH2Cl2
18: TsOH/acetone
19: K2CO3/MeOH
20: 1.) NaOCl2 / 1.) 2-methyl-2-butene, t-BuOH, 2.) Et2O
21: Ba(OH)2 / methanol; H2O
22: 2-chloro-1-methylpyridinium iodide, DMAP / CH2Cl2
With
methanol; dmap; barium dihydroxide; lithium aluminium tetrahydride; dipyridinium dichromate; oxalyl dichloride; naphthalene; camphor-10-sulfonic acid; 2-chloro-1-methyl-pyridinium iodide; sodium; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; acetone; hydrazine;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1016/S0040-4039(00)74295-X