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Technology Process of N-{4-[{3-[(2R,6S)-6-((1S,2R)-1,2-Bis-benzyloxy-heptyl)-2-(2,2-dimethoxy-ethyl)-3,6-dihydro-2H-pyridin-1-yl]-propyl}-(toluene-4-sulfonyl)-amino]-butyl}-2,2,2-trifluoro-acetamide

N-{4-[{3-[(2R,6S)-6-((1S,2R)-1,2-Bis-benzyloxy-heptyl)-2-(2,2-dimethoxy-ethyl)-3,6-dihydro-2H-pyridin-1-yl]-propyl}-(toluene-4-sulfonyl)-amino]-butyl}-2,2,2-trifluoro-acetamide

Base Information
  • Chemical Name:N-{4-[{3-[(2R,6S)-6-((1S,2R)-1,2-Bis-benzyloxy-heptyl)-2-(2,2-dimethoxy-ethyl)-3,6-dihydro-2H-pyridin-1-yl]-propyl}-(toluene-4-sulfonyl)-amino]-butyl}-2,2,2-trifluoro-acetamide
  • CAS No.:135068-33-6
  • Molecular Formula:C46H64F3N3O7S
  • Molecular Weight:860.091
  • Hs Code.:
N-{4-[{3-[(2R,6S)-6-((1S,2R)-1,2-Bis-benzyloxy-heptyl)-2-(2,2-dimethoxy-ethyl)-3,6-dihydro-2H-pyridin-1-yl]-propyl}-(toluene-4-sulfonyl)-amino]-butyl}-2,2,2-trifluoro-acetamide

Synonyms:

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Chemical Property of N-{4-[{3-[(2R,6S)-6-((1S,2R)-1,2-Bis-benzyloxy-heptyl)-2-(2,2-dimethoxy-ethyl)-3,6-dihydro-2H-pyridin-1-yl]-propyl}-(toluene-4-sulfonyl)-amino]-butyl}-2,2,2-trifluoro-acetamide
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Technology Process of N-{4-[{3-[(2R,6S)-6-((1S,2R)-1,2-Bis-benzyloxy-heptyl)-2-(2,2-dimethoxy-ethyl)-3,6-dihydro-2H-pyridin-1-yl]-propyl}-(toluene-4-sulfonyl)-amino]-butyl}-2,2,2-trifluoro-acetamide

There total 19 articles about N-{4-[{3-[(2R,6S)-6-((1S,2R)-1,2-Bis-benzyloxy-heptyl)-2-(2,2-dimethoxy-ethyl)-3,6-dihydro-2H-pyridin-1-yl]-propyl}-(toluene-4-sulfonyl)-amino]-butyl}-2,2,2-trifluoro-acetamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

Tetrakis(benzyloxy)titanium
19803-37-3

Tetrakis(benzyloxy)titanium

N-{4-[{3-[(2R,6S)-6-((1S,2R)-1,2-Bis-benzyloxy-heptyl)-2-(2,2-dimethoxy-ethyl)-3,6-dihydro-2H-pyridin-1-yl]-propyl}-(toluene-4-sulfonyl)-amino]-butyl}-2,2,2-trifluoro-acetamide
135068-33-6

N-{4-[{3-[(2R,6S)-6-((1S,2R)-1,2-Bis-benzyloxy-heptyl)-2-(2,2-dimethoxy-ethyl)-3,6-dihydro-2H-pyridin-1-yl]-propyl}-(toluene-4-sulfonyl)-amino]-butyl}-2,2,2-trifluoro-acetamide

Guidance literature:
Multi-step reaction with 17 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
With lithium aluminium tetrahydride; dipyridinium dichromate; oxalyl dichloride; naphthalene; camphor-10-sulfonic acid; sodium; sodium hydride; diisobutylaluminium hydride; potassium carbonate; triethylamine; hydrazine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1016/S0040-4039(00)74295-X

Reference yield:

[(2S,3S)-3-pentyloxiran-2-yl]methanol
89461-51-8

[(2S,3S)-3-pentyloxiran-2-yl]methanol

N-{4-[{3-[(2R,6S)-6-((1S,2R)-1,2-Bis-benzyloxy-heptyl)-2-(2,2-dimethoxy-ethyl)-3,6-dihydro-2H-pyridin-1-yl]-propyl}-(toluene-4-sulfonyl)-amino]-butyl}-2,2,2-trifluoro-acetamide
135068-33-6

N-{4-[{3-[(2R,6S)-6-((1S,2R)-1,2-Bis-benzyloxy-heptyl)-2-(2,2-dimethoxy-ethyl)-3,6-dihydro-2H-pyridin-1-yl]-propyl}-(toluene-4-sulfonyl)-amino]-butyl}-2,2,2-trifluoro-acetamide

Guidance literature:
Multi-step reaction with 17 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
With lithium aluminium tetrahydride; dipyridinium dichromate; oxalyl dichloride; naphthalene; camphor-10-sulfonic acid; sodium; sodium hydride; diisobutylaluminium hydride; potassium carbonate; triethylamine; hydrazine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1016/S0040-4039(00)74295-X

Reference yield:

benzyl chloride
100-44-7

benzyl chloride

N-{4-[{3-[(2R,6S)-6-((1S,2R)-1,2-Bis-benzyloxy-heptyl)-2-(2,2-dimethoxy-ethyl)-3,6-dihydro-2H-pyridin-1-yl]-propyl}-(toluene-4-sulfonyl)-amino]-butyl}-2,2,2-trifluoro-acetamide
135068-33-6

N-{4-[{3-[(2R,6S)-6-((1S,2R)-1,2-Bis-benzyloxy-heptyl)-2-(2,2-dimethoxy-ethyl)-3,6-dihydro-2H-pyridin-1-yl]-propyl}-(toluene-4-sulfonyl)-amino]-butyl}-2,2,2-trifluoro-acetamide

Guidance literature:
Multi-step reaction with 17 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
With lithium aluminium tetrahydride; dipyridinium dichromate; oxalyl dichloride; naphthalene; camphor-10-sulfonic acid; sodium; sodium hydride; diisobutylaluminium hydride; potassium carbonate; triethylamine; hydrazine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1016/S0040-4039(00)74295-X
upstream raw materials:

trifluoroacetic anhydride

Tetrakis(benzyloxy)titanium

[(2S,3S)-3-pentyloxiran-2-yl]methanol

benzyl chloride

Downstream raw materials:

(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

[(2S,6S)-6-((1S,2R)-1,2-Bis-benzyloxy-heptyl)-1-(3-{(toluene-4-sulfonyl)-[4-(2,2,2-trifluoro-acetylamino)-butyl]-amino}-propyl)-1,2,3,6-tetrahydro-pyridin-2-yl]-acetic acid methyl ester

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