(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

Base Information

• Chemical Name: (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
• CAS No.: 454482-54-3
• Molecular Formula: C₂₉H₄₁NO₅S
• Molecular Weight: 515.714

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Technology Process of (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

There total 3 articles about (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 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: 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

Reference yield:

4-Methoxybenzyl alcohol (105-13-5) → (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:

Multi-step reaction with 3 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

3.1: KHMDS / tetrahydrofuran; toluene / 1.5 h / -78 °C

3.2: 64 percent / HMPA / tetrahydrofuran; toluene / 1.17 h / -78 °C

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

DOI:10.1055/s-2002-28511

Reference yield:

1-(((2-(chloromethyl)allyl)oxy)methyl)-4-methoxybenzene (454482-62-3) → (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:

Multi-step reaction with 2 steps

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

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

1.3: 98 percent / TMSCl / tetrahydrofuran / 1.5 h / -78 °C

2.1: KHMDS / tetrahydrofuran; toluene / 1.5 h / -78 °C

2.2: 64 percent / HMPA / tetrahydrofuran; toluene / 1.17 h / -78 °C

With potassium hexamethylsilazane; magnesium; ethylene dibromide; In tetrahydrofuran; toluene;

DOI:10.1055/s-2002-28511

upstream raw materials:

allyl iodid

(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

4-Methoxybenzyl alcohol

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

Downstream raw materials:

((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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