(2S,4aR,6S,9R,9aS)-9-Benzenesulfonylmethyl-6-[(S)-2-benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-propyl]-2-(tert-butyl-diphenyl-silanyloxymethyl)-4a,6,9,9a-tetrahydro-2H-1,5-dioxa-benzocycloheptene

Base Information

• Chemical Name: (2S,4aR,6S,9R,9aS)-9-Benzenesulfonylmethyl-6-[(S)-2-benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-propyl]-2-(tert-butyl-diphenyl-silanyloxymethyl)-4a,6,9,9a-tetrahydro-2H-1,5-dioxa-benzocycloheptene
• CAS No.: 287194-54-1
• Molecular Formula: C₅₉H₆₈O₇SSi₂
• Molecular Weight: 977.422
• Mol file: 287194-54-1.mol

Synonyms:(2S,4aR,6S,9R,9aS)-9-Benzenesulfonylmethyl-6-[(S)-2-benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-propyl]-2-(tert-butyl-diphenyl-silanyloxymethyl)-4a,6,9,9a-tetrahydro-2H-1,5-dioxa-benzocycloheptene

Chemical Property of (2S,4aR,6S,9R,9aS)-9-Benzenesulfonylmethyl-6-[(S)-2-benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-propyl]-2-(tert-butyl-diphenyl-silanyloxymethyl)-4a,6,9,9a-tetrahydro-2H-1,5-dioxa-benzocycloheptene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4aR,6S,9R,9aS)-9-Benzenesulfonylmethyl-6-[(S)-2-benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-propyl]-2-(tert-butyl-diphenyl-silanyloxymethyl)-4a,6,9,9a-tetrahydro-2H-1,5-dioxa-benzocycloheptene

There total 8 articles about (2S,4aR,6S,9R,9aS)-9-Benzenesulfonylmethyl-6-[(S)-2-benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-propyl]-2-(tert-butyl-diphenyl-silanyloxymethyl)-4a,6,9,9a-tetrahydro-2H-1,5-dioxa-benzocycloheptene 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:

2-[1-benzenesulfonylmethyl-6-benzyloxy-7-(tert-butyldiphenylsilyloxy)-1-ethyl-4-methoxy-hex-2-ynyl]-6-(tert-butyldiphenylsilyloxymethyl)-3,6-dihydro-2H-pyran-3-ol (287194-52-9) → (2S,4aR,6S,9R,9aS)-9-Benzenesulfonylmethyl-6-[(S)-2-benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-propyl]-2-(tert-butyl-diphenyl-silanyloxymethyl)-4a,6,9,9a-tetrahydro-2H-1,5-dioxa-benzocycloheptene (287194-54-1)

Guidance literature:

2-[1-benzenesulfonylmethyl-6-benzyloxy-7-(tert-butyldiphenylsilyloxy)-1-ethyl-4-methoxy-hex-2-ynyl]-6-(tert-butyldiphenylsilyloxymethyl)-3,6-dihydro-2H-pyran-3-ol; With dicobalt octacarbonyl; In dichloromethane; at 20 ℃; pH=0;

With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 0.833333h;

With tri-n-butyl-tin hydride; In toluene; at 55 ℃;

Reference yield:

(2-benzyloxy-4-methoxy-hex-5-ynyloxy)-tert-butyl-diphenyl-silane (287194-42-7) → (2S,4aR,6S,9R,9aS)-9-Benzenesulfonylmethyl-6-[(S)-2-benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-propyl]-2-(tert-butyl-diphenyl-silanyloxymethyl)-4a,6,9,9a-tetrahydro-2H-1,5-dioxa-benzocycloheptene (287194-54-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

1.2: 82 percent / TBAF / tetrahydrofuran / 0.08 h / 0 °C

2.1: Co₂(CO)8 / CH₂Cl₂ / 2 h / 20 °C

2.2: BF₃*OEt₂ / CH₂Cl₂ / 0.92 h / 0 °C

2.3: n-Bu₃SnH / toluene / 2 h / 55 °C

With n-butyllithium; dicobalt octacarbonyl; In tetrahydrofuran; hexane; dichloromethane; 1.1: Addition / 1.2: Hydrolysis / 2.1: complexation / 2.2: Cyclization / 2.3: Reduction;

DOI:10.1016/S0040-4020(00)00467-1

Reference yield:

1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-4-trimethylsilylbut-3-yn-2-ol (272787-64-1) → (2S,4aR,6S,9R,9aS)-9-Benzenesulfonylmethyl-6-[(S)-2-benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-propyl]-2-(tert-butyl-diphenyl-silanyloxymethyl)-4a,6,9,9a-tetrahydro-2H-1,5-dioxa-benzocycloheptene (287194-54-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 83 percent / KOH / dimethylsulfoxide / 0.17 h / 20 °C

2.1: 93 percent / TsOH / methanol / 20 °C

3.1: 85 percent / Et₃N; DMAP / CH₂Cl₂

4.1: 89 percent / NaH / dimethylformamide / 0 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

5.2: 82 percent / TBAF / tetrahydrofuran / 0.08 h / 0 °C

6.1: Co₂(CO)8 / CH₂Cl₂ / 2 h / 20 °C

6.2: BF₃*OEt₂ / CH₂Cl₂ / 0.92 h / 0 °C

6.3: n-Bu₃SnH / toluene / 2 h / 55 °C

With dmap; potassium hydroxide; n-butyllithium; dicobalt octacarbonyl; sodium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 1.1: Methylation / 2.1: Hydrolysis / 3.1: silylation / 4.1: Alkylation / 5.1: Addition / 5.2: Hydrolysis / 6.1: complexation / 6.2: Cyclization / 6.3: Reduction;

DOI:10.1016/S0040-4020(00)00467-1

upstream raw materials:

2-[1-benzenesulfonylmethyl-6-benzyloxy-7-(tert-butyldiphenylsilyloxy)-1-ethyl-4-methoxy-hex-2-ynyl]-6-(tert-butyldiphenylsilyloxymethyl)-3,6-dihydro-2H-pyran-3-ol

1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-4-trimethylsilylbut-3-yn-2-ol

4-(2-methoxybut-3-ynyl)-2,2-dimethyl-[1,3]dioxolane

(2-benzyloxy-4-methoxy-hex-5-ynyloxy)-tert-butyl-diphenyl-silane

Downstream raw materials:

(2S,4aR,6S,9R,9aS)-6-[(S)-2-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-propyl]-2-(tert-butyl-diphenyl-silanyloxymethyl)-9-methyl-4a,6,9,9a-tetrahydro-2H-1,5-dioxa-benzocycloheptene

(S)-2-Benzyloxy-3-((2S,4aR,6S,9R,9aS)-2-hydroxymethyl-9-methyl-4a,6,9,9a-tetrahydro-2H-1,5-dioxa-benzocyclohepten-6-yl)-propan-1-ol