(S)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-5-(4-methoxy-benzyloxymethyl)-3-methyl-hex-5-en-1-one

Base Information

• Chemical Name: (S)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-5-(4-methoxy-benzyloxymethyl)-3-methyl-hex-5-en-1-one
• CAS No.: 454482-52-1
• Molecular Formula: C₂₆H₃₇NO₅S
• Molecular Weight: 475.649

Synonyms:(S)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-5-(4-methoxy-benzyloxymethyl)-3-methyl-hex-5-en-1-one

Chemical Property of (S)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-5-(4-methoxy-benzyloxymethyl)-3-methyl-hex-5-en-1-one

Chemical Property:

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Technology Process of (S)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-5-(4-methoxy-benzyloxymethyl)-3-methyl-hex-5-en-1-one

There total 2 articles about (S)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-5-(4-methoxy-benzyloxymethyl)-3-methyl-hex-5-en-1-one 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: 98.0%

(E)-1-((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)but-2-en-1-one (94594-81-7) + 1-(((2-(chloromethyl)allyl)oxy)methyl)-4-methoxybenzene (454482-62-3) → (S)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-5-(4-methoxy-benzyloxymethyl)-3-methyl-hex-5-en-1-one (454482-52-1)

Guidance literature:

1-(((2-(chloromethyl)allyl)oxy)methyl)-4-methoxybenzene; With magnesium; ethylene dibromide; In tetrahydrofuran; at -5 - 20 ℃; for 1.5h;

With copper(I) bromide dimethylsulfide complex; lithium chloride; In tetrahydrofuran; at -78 ℃;

(E)-1-((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)but-2-en-1-one; With chloro-trimethyl-silane; In tetrahydrofuran; at -78 ℃; for 1.5h;

DOI:10.1055/s-2002-28511

Reference yield:

4-Methoxybenzyl alcohol (105-13-5) → (S)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-5-(4-methoxy-benzyloxymethyl)-3-methyl-hex-5-en-1-one (454482-52-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / tetrahydrofuran; dimethylformamide / 1.5 h

1.2: 75 percent / tetrahydrofuran; dimethylformamide / 20 °C

2.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 1.5 h / -5 - 20 °C

2.2: CuBr*Me₂S; LiCl / tetrahydrofuran / -78 °C

2.3: 98 percent / TMSCl / tetrahydrofuran / 1.5 h / -78 °C

With sodium hydride; magnesium; ethylene dibromide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1055/s-2002-28511

Reference yield: 64.0%

allyl iodid (556-56-9) + (S)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-5-(4-methoxy-benzyloxymethyl)-3-methyl-hex-5-en-1-one (454482-52-1) → (2S,3S)-2-Allyl-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-5-(4-methoxy-benzyloxymethyl)-3-methyl-hex-5-en-1-one (454482-54-3)

Guidance literature:

(S)-1-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-5-(4-methoxy-benzyloxymethyl)-3-methyl-hex-5-en-1-one; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 1.5h;

allyl iodid; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; toluene; at -78 ℃; for 1.16667h;

DOI:10.1055/s-2002-28511

upstream raw materials:

(E)-1-((3aR,6S,7aS)-8,8-dimethyl-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)but-2-en-1-one

1-(((2-(chloromethyl)allyl)oxy)methyl)-4-methoxybenzene

4-Methoxybenzyl alcohol

Downstream raw materials:

(2S,3S)-2-Allyl-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-5-(4-methoxy-benzyloxymethyl)-3-methyl-hex-5-en-1-one

((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-((1S,6S)-4-hydroxymethyl-6-methyl-cyclohex-3-enyl)-methanone

((1R,3S,4S,6R)-6-Benzyloxymethyl-4-methyl-7-oxa-bicyclo[4.1.0]hept-3-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

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