{(S)-6-[4-(tert-Butyl-diphenyl-silanyloxy)-butyl]-1-oxy-2,3,4,5-tetrahydro-pyridin-2-yl}-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-methanone

Base Information

• Chemical Name: {(S)-6-[4-(tert-Butyl-diphenyl-silanyloxy)-butyl]-1-oxy-2,3,4,5-tetrahydro-pyridin-2-yl}-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-methanone
• CAS No.: 233757-50-1
• Molecular Formula: C₃₆H₅₀N₂O₅SSi
• Molecular Weight: 650.955

Synonyms:{(S)-6-[4-(tert-Butyl-diphenyl-silanyloxy)-butyl]-1-oxy-2,3,4,5-tetrahydro-pyridin-2-yl}-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-methanone

Chemical Property of {(S)-6-[4-(tert-Butyl-diphenyl-silanyloxy)-butyl]-1-oxy-2,3,4,5-tetrahydro-pyridin-2-yl}-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-methanone

Chemical Property:

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Technology Process of {(S)-6-[4-(tert-Butyl-diphenyl-silanyloxy)-butyl]-1-oxy-2,3,4,5-tetrahydro-pyridin-2-yl}-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-methanone

There total 12 articles about {(S)-6-[4-(tert-Butyl-diphenyl-silanyloxy)-butyl]-1-oxy-2,3,4,5-tetrahydro-pyridin-2-yl}-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-methanone 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:

(2S,2'S)-N-[10'-(tert-butyldiphenylsilyloxy)-2'-hydroxyaminodec-6'-ynoyl]bornane-10,2-sultam (233757-48-7) → {(S)-6-[4-(tert-Butyl-diphenyl-silanyloxy)-butyl]-1-oxy-2,3,4,5-tetrahydro-pyridin-2-yl}-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-methanone (233757-50-1)

Guidance literature:

In toluene; at 80 ℃; for 6h;

DOI:10.1021/ja990138l

Reference yield:

10-(tert-butyldiphenylsilyloxy)dec-6-yn-1-ol (233757-70-5) → {(S)-6-[4-(tert-Butyl-diphenyl-silanyloxy)-butyl]-1-oxy-2,3,4,5-tetrahydro-pyridin-2-yl}-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-methanone (233757-50-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 98 percent / CrO₃; H₂SO₄ / acetone / 3 h / 0 °C

2.1: Et₃N / tetrahydrofuran / 1 h / 25 °C

3.1: n-BuLi; pyren-1-ylacetic acid / tetrahydrofuran; hexane / 0.33 h / -78 °C

3.2: 3.54 g / tetrahydrofuran; hexane / 1.5 h / 25 °C

4.1: NaHMDS / tetrahydrofuran / 0.02 h / -78 °C

4.2: 1-chloro-1-nitrosocyclohexane / tetrahydrofuran / 0.5 h / -78 °C

4.3: 77 percent / aq. HCl / tetrahydrofuran / 1 h / 25 °C

5.1: toluene / 7 h / 75 °C

With chromium(VI) oxide; n-butyllithium; sulfuric acid; 1-pyreneacetic acid; sodium hexamethyldisilazane; triethylamine; In tetrahydrofuran; hexane; acetone; toluene;

DOI:10.1039/b200328g

Reference yield:

10-(tert-butyldiphenylsilyloxy)dec-6-ynoic acid (233757-44-3) → {(S)-6-[4-(tert-Butyl-diphenyl-silanyloxy)-butyl]-1-oxy-2,3,4,5-tetrahydro-pyridin-2-yl}-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-methanone (233757-50-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Et₃N / tetrahydrofuran / 1 h / 25 °C

2.1: n-BuLi; pyren-1-ylacetic acid / tetrahydrofuran; hexane / 0.33 h / -78 °C

2.2: 3.54 g / tetrahydrofuran; hexane / 1.5 h / 25 °C

3.1: NaHMDS / tetrahydrofuran / 0.02 h / -78 °C

3.2: 1-chloro-1-nitrosocyclohexane / tetrahydrofuran / 0.5 h / -78 °C

3.3: 77 percent / aq. HCl / tetrahydrofuran / 1 h / 25 °C

4.1: toluene / 7 h / 75 °C

With n-butyllithium; 1-pyreneacetic acid; sodium hexamethyldisilazane; triethylamine; In tetrahydrofuran; hexane; toluene;

DOI:10.1039/b200328g

upstream raw materials:

(2S,2'S)-N-[10'-(tert-butyldiphenylsilyloxy)-2'-hydroxyaminodec-6'-ynoyl]bornane-10,2-sultam

pent-1-yn-5-ol

5-(benzyloxy)-1-pentanol

(((5-iodopentyl)oxy)methyl)benzene

Downstream raw materials:

(2S,2'S,6'R,8'R)-N-{6'-[4''-(tert-butyldiphenylsilyloxy)-1''-butyl]-8'-phenyl-1'-aza-9'-oxabicyclo[4.3.0]nonan-2'-ylcarbonyl}bornane-10,2-sultam

(-)-histrionicotoxin

(2S,6R,8R)-2-(benzyloxymethyl)-6-(3'-formyl-1'-propyl)-8-phenyl-1-aza-9-oxabicyclo[4.3.0]nonane

(2S,6R,8R)-2-(benzyloxymethyl)-6-(4'-hydroxy-1'-butyl)-8-phenyl-1-aza-9-oxabicyclo[4.3.0]nonane

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