(-)-[S_S,N(1S),3S,7R]-N-{1-[tert-butyl(dimethyl)silanyloxymethyl]-2-methyl-propyl}-2-(3-hydroxy-3-{8-[1-(p-tolyl-sulfonimidoyl)meth-(Z)-ylidene]-1,4-dioxa-spiro[4.5]dec-7-yl}propyl)isoindole-1,3-dione

Base Information

• Chemical Name: (-)-[S_S,N(1S),3S,7R]-N-{1-[tert-butyl(dimethyl)silanyloxymethyl]-2-methyl-propyl}-2-(3-hydroxy-3-{8-[1-(p-tolyl-sulfonimidoyl)meth-(Z)-ylidene]-1,4-dioxa-spiro[4.5]dec-7-yl}propyl)isoindole-1,3-dione
• CAS No.: 911381-65-2
• Molecular Formula: C₃₈H₅₄N₂O₇SSi
• Molecular Weight: 711.007

Synonyms:(-)-[S_S,N(1S),3S,7R]-N-{1-[tert-butyl(dimethyl)silanyloxymethyl]-2-methyl-propyl}-2-(3-hydroxy-3-{8-[1-(p-tolyl-sulfonimidoyl)meth-(Z)-ylidene]-1,4-dioxa-spiro[4.5]dec-7-yl}propyl)isoindole-1,3-dione

Chemical Property of (-)-[S_S,N(1S),3S,7R]-N-{1-[tert-butyl(dimethyl)silanyloxymethyl]-2-methyl-propyl}-2-(3-hydroxy-3-{8-[1-(p-tolyl-sulfonimidoyl)meth-(Z)-ylidene]-1,4-dioxa-spiro[4.5]dec-7-yl}propyl)isoindole-1,3-dione

Chemical Property:

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Technology Process of (-)-[S_S,N(1S),3S,7R]-N-{1-[tert-butyl(dimethyl)silanyloxymethyl]-2-methyl-propyl}-2-(3-hydroxy-3-{8-[1-(p-tolyl-sulfonimidoyl)meth-(Z)-ylidene]-1,4-dioxa-spiro[4.5]dec-7-yl}propyl)isoindole-1,3-dione

There total 5 articles about (-)-[S_S,N(1S),3S,7R]-N-{1-[tert-butyl(dimethyl)silanyloxymethyl]-2-methyl-propyl}-2-(3-hydroxy-3-{8-[1-(p-tolyl-sulfonimidoyl)meth-(Z)-ylidene]-1,4-dioxa-spiro[4.5]dec-7-yl}propyl)isoindole-1,3-dione 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: 81.0%

(+)-[SS,N(1S)]-N-{1-[tert-butyl(dimethyl)silanyloxymethyl]-2-methyl-propyl}-4-(p-tolyl-sulfonimidomethyl)-1,4-dioxa-spiro[4.5]dec-7-ene (911381-59-4) + 3-(N-phthaloyl)propionaldehyde (2436-29-5) → (-)-[SS,N(1S),3S,7R]-N-{1-[tert-butyl(dimethyl)silanyloxymethyl]-2-methyl-propyl}-2-(3-hydroxy-3-{8-[1-(p-tolyl-sulfonimidoyl)meth-(Z)-ylidene]-1,4-dioxa-spiro[4.5]dec-7-yl}propyl)isoindole-1,3-dione (911381-65-2)

Guidance literature:

(+)-[S_S,N(1S)]-N-{1-[tert-butyl(dimethyl)silanyloxymethyl]-2-methyl-propyl}-4-(p-tolyl-sulfonimidomethyl)-1,4-dioxa-spiro[4.5]dec-7-ene; With n-butyllithium; In hexane; toluene; at -78 ℃; for 0.25h;

With triisopropoxytitanium(IV) chloride; In hexane; toluene; at -78 - 20 ℃; for 1.25h;

3-(N-phthaloyl)propionaldehyde; In tetrahydrofuran; hexane; toluene; at 0 ℃; Further stages.;

DOI:10.1055/s-2006-942427

Reference yield:

C19H35NO2SSi → (-)-[SS,N(1S),3S,7R]-N-{1-[tert-butyl(dimethyl)silanyloxymethyl]-2-methyl-propyl}-2-(3-hydroxy-3-{8-[1-(p-tolyl-sulfonimidoyl)meth-(Z)-ylidene]-1,4-dioxa-spiro[4.5]dec-7-yl}propyl)isoindole-1,3-dione (911381-65-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

1.2: tetrahydrofuran; hexane / 0.67 h / -78 - 20 °C

2.1: Me₂NEt; 4-dimethylaminopyridine / CH₂Cl₂ / 20 °C

3.1: 2.09 g / KO-t-Bu; n-BuLi / toluene; hexane / -78 - 20 °C

4.1: n-BuLi / toluene; hexane / 0.25 h / -78 °C

4.2: ClTi(O-i-Pr)3 / toluene; hexane / 1.25 h / -78 - 20 °C

4.3: 81 percent / toluene; hexane; tetrahydrofuran / 0 °C

With dmap; n-butyllithium; N,N-dimethyl-ethanamine; potassium tert-butylate; In tetrahydrofuran; hexane; dichloromethane; toluene;

DOI:10.1055/s-2006-942427

Reference yield:

C30H55NO5SSi2 → (-)-[SS,N(1S),3S,7R]-N-{1-[tert-butyl(dimethyl)silanyloxymethyl]-2-methyl-propyl}-2-(3-hydroxy-3-{8-[1-(p-tolyl-sulfonimidoyl)meth-(Z)-ylidene]-1,4-dioxa-spiro[4.5]dec-7-yl}propyl)isoindole-1,3-dione (911381-65-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 2.09 g / KO-t-Bu; n-BuLi / toluene; hexane / -78 - 20 °C

2.1: n-BuLi / toluene; hexane / 0.25 h / -78 °C

2.2: ClTi(O-i-Pr)3 / toluene; hexane / 1.25 h / -78 - 20 °C

2.3: 81 percent / toluene; hexane; tetrahydrofuran / 0 °C

With n-butyllithium; potassium tert-butylate; In hexane; toluene;

DOI:10.1055/s-2006-942427

upstream raw materials:

(+)-[S_S,N(1S)]-N-{1-[tert-butyl(dimethyl)silanyloxymethyl]-2-methyl-propyl}-4-(p-tolyl-sulfonimidomethyl)-1,4-dioxa-spiro[4.5]dec-7-ene

3-(N-phthaloyl)propionaldehyde

cyclohexanedione monoethylene ketal

Downstream raw materials:

(+)-[S_S,N(1S),4S,4aR,8aS]-N-{1-[tert-butyl(dimethyl)silanyloxymethyl]-2-methyl-propyl}-4-hydroxy-8a-(p-tolyl-sulfonimidoylmethyl)octahydro-quinolin-6-one-ethylene-ketal

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