((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

Base Information

• Chemical Name: ((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
• CAS No.: 454482-58-7
• Molecular Formula: C₂₆H₃₅NO₅S
• Molecular Weight: 473.634

Synonyms:((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

Chemical Property of ((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

Chemical Property:

Purity/Quality:

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Technology Process of ((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

There total 5 articles about ((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 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: 20.0%

benzyl bromide (100-39-0) + ((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-((1R,3S,4S,6R)-6-hydroxymethyl-4-methyl-7-oxa-bicyclo[4.1.0]hept-3-yl)-methanone (454482-57-6) → ((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[5.2.1.01,5]dec-4-yl)-methanone (454482-58-7)

Guidance literature:

((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-((1R,3S,4S,6R)-6-hydroxymethyl-4-methyl-7-oxa-bicyclo[4.1.0]hept-3-yl)-methanone; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.166667h;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; at 0 - 20 ℃;

DOI:10.1055/s-2002-28511

Reference yield:

(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-hydroxymethyl-3-methyl-hex-5-en-1-one (454482-55-4) → ((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[5.2.1.01,5]dec-4-yl)-methanone (454482-58-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 97 percent / Grubb's catalyst / CH₂Cl₂ / 23 h / 20 °C

2.1: (-)-diethyl tartrate; Ti(i-PrO)4; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.33 h / -20 °C

2.2: 84 percent / tert-butyl hydroperoxide / CH₂Cl₂ / 3 h / -20 °C

3.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

3.2: 20 percent / tetra-N-butylammonium iodide / 0 - 20 °C

With titanium(IV) isopropylate; 4 A molecular sieve; sodium hydride; (-)-diethyl tartrate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; 2.2: Sharpless epoxidation;

DOI:10.1055/s-2002-28511

Reference yield:

(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) → ((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[5.2.1.01,5]dec-4-yl)-methanone (454482-58-7)

Guidance literature:

Multi-step reaction with 5 steps

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

1.2: 64 percent / HMPA / tetrahydrofuran; toluene / 1.17 h / -78 °C

2.1: 97 percent / DDQ; H₂O / CH₂Cl₂ / 0.75 h

3.1: 97 percent / Grubb's catalyst / CH₂Cl₂ / 23 h / 20 °C

4.1: (-)-diethyl tartrate; Ti(i-PrO)4; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.33 h / -20 °C

4.2: 84 percent / tert-butyl hydroperoxide / CH₂Cl₂ / 3 h / -20 °C

5.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

5.2: 20 percent / tetra-N-butylammonium iodide / 0 - 20 °C

With titanium(IV) isopropylate; 4 A molecular sieve; water; potassium hexamethylsilazane; sodium hydride; (-)-diethyl tartrate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; toluene; 4.2: Sharpless epoxidation;

DOI:10.1055/s-2002-28511

upstream raw materials:

benzyl bromide

((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-((1R,3S,4S,6R)-6-hydroxymethyl-4-methyl-7-oxa-bicyclo[4.1.0]hept-3-yl)-methanone

((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

(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-hydroxymethyl-3-methyl-hex-5-en-1-one

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