(6-{[4-(tert-butyl-dimethyl-silanyloxy)-1,1-dioxo-hexahydro-1λ⁶-thiopyran-3-yl]-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionyl]-amino}-hexyl)-carbamic acid tert-butyl ester

Base Information

• Chemical Name: (6-{[4-(tert-butyl-dimethyl-silanyloxy)-1,1-dioxo-hexahydro-1λ⁶-thiopyran-3-yl]-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionyl]-amino}-hexyl)-carbamic acid tert-butyl ester
• CAS No.: 868700-47-4
• Molecular Formula: C₄₆H₆₅N₃O₈SSi
• Molecular Weight: 848.189

Synonyms:

Chemical Property of (6-{[4-(tert-butyl-dimethyl-silanyloxy)-1,1-dioxo-hexahydro-1λ⁶-thiopyran-3-yl]-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionyl]-amino}-hexyl)-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (6-{[4-(tert-butyl-dimethyl-silanyloxy)-1,1-dioxo-hexahydro-1λ⁶-thiopyran-3-yl]-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionyl]-amino}-hexyl)-carbamic acid tert-butyl ester

There total 10 articles about (6-{[4-(tert-butyl-dimethyl-silanyloxy)-1,1-dioxo-hexahydro-1λ⁶-thiopyran-3-yl]-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionyl]-amino}-hexyl)-carbamic acid tert-butyl ester 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:

tert-Butyl-((3R,4R)-3-isocyanato-tetrahydro-thiopyran-4-yloxy)-dimethyl-silane → (6-{[4-(tert-butyl-dimethyl-silanyloxy)-1,1-dioxo-hexahydro-1λ6-thiopyran-3-yl]-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionyl]-amino}-hexyl)-carbamic acid tert-butyl ester (868700-47-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / 0 °C

1.2: 3.60 g / tetrahydrofuran; hexane / 0.5 h / 0 - 20 °C

2.1: 74 percent / NaIO₄; KMnO₄; NaHCO₃ / acetone; H₂O / 6 h / 20 °C

3.1: 100 percent / H₂ / Pd/C / methanol / 5 h / 20 °C / 760 Torr

4.1: 1,2-dichloro-ethane / 0.42 h

5.1: 387 mg / sodium triacetoxyborohydride / 1,2-dichloro-ethane / 5 h / 20 °C

6.1: acetonitrile / 2 h / 20 °C

7.1: 230 mg / tetrabutylammonium fluoride / acetonitrile / 4 h / 60 °C

With potassium permanganate; sodium periodate; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; water; 1,2-dichloro-ethane; acetone; acetonitrile;

DOI:10.1021/jo0508954

Reference yield:

(3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-tetrahydro-thiopyran-3-carboxylic acid → (6-{[4-(tert-butyl-dimethyl-silanyloxy)-1,1-dioxo-hexahydro-1λ6-thiopyran-3-yl]-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionyl]-amino}-hexyl)-carbamic acid tert-butyl ester (868700-47-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: diphenylphosphoryl azide; N,N-diisopropylethylamine / toluene / 4 h / 60 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / 0 °C

2.2: 3.60 g / tetrahydrofuran; hexane / 0.5 h / 0 - 20 °C

3.1: 74 percent / NaIO₄; KMnO₄; NaHCO₃ / acetone; H₂O / 6 h / 20 °C

4.1: 100 percent / H₂ / Pd/C / methanol / 5 h / 20 °C / 760 Torr

5.1: 1,2-dichloro-ethane / 0.42 h

6.1: 387 mg / sodium triacetoxyborohydride / 1,2-dichloro-ethane / 5 h / 20 °C

7.1: acetonitrile / 2 h / 20 °C

8.1: 230 mg / tetrabutylammonium fluoride / acetonitrile / 4 h / 60 °C

With potassium permanganate; sodium periodate; n-butyllithium; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; hydrogen; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; water; 1,2-dichloro-ethane; acetone; toluene; acetonitrile; 1.1: Curtius rearrangement;

DOI:10.1021/jo0508954

Reference yield:

(3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-tetrahydro-thiopyran-3-carboxylic acid methyl ester → (6-{[4-(tert-butyl-dimethyl-silanyloxy)-1,1-dioxo-hexahydro-1λ6-thiopyran-3-yl]-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenyl-propionyl]-amino}-hexyl)-carbamic acid tert-butyl ester (868700-47-4)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 70 percent / aq. NaOH / methanol / 24 h / Heating

2.1: diphenylphosphoryl azide; N,N-diisopropylethylamine / toluene / 4 h / 60 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / 0 °C

3.2: 3.60 g / tetrahydrofuran; hexane / 0.5 h / 0 - 20 °C

4.1: 74 percent / NaIO₄; KMnO₄; NaHCO₃ / acetone; H₂O / 6 h / 20 °C

5.1: 100 percent / H₂ / Pd/C / methanol / 5 h / 20 °C / 760 Torr

6.1: 1,2-dichloro-ethane / 0.42 h

7.1: 387 mg / sodium triacetoxyborohydride / 1,2-dichloro-ethane / 5 h / 20 °C

8.1: acetonitrile / 2 h / 20 °C

9.1: 230 mg / tetrabutylammonium fluoride / acetonitrile / 4 h / 60 °C

With sodium hydroxide; potassium permanganate; sodium periodate; n-butyllithium; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; hydrogen; sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; water; 1,2-dichloro-ethane; acetone; toluene; acetonitrile; 2.1: Curtius rearrangement;

DOI:10.1021/jo0508954

upstream raw materials:

3-methoxycarbonyltetrahydropyran-4-one

Downstream raw materials:

(6-{[2-(2-tert-butoxycarbonylamino-3-methyl-pentanoylamino)-3-phenyl-propionyl]-[4-(tert-butyl-dimethyl-silanyloxy)-1,1-dioxo-hexahydro-1λ⁶-thiopyran-3-yl]-amino}-hexyl)-carbamic acid tert-butyl ester

{6-[[2-(2-tert-butoxycarbonylamino-3-methyl-pentanoylamino)-3-phenyl-propionyl]-(1,1,4-trioxo-hexahydro-1λ⁶-thiopyran-3-yl)-amino]-hexyl}-carbamic acid tert-butyl ester

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