(4S,5R,7R)-9-(tert-butyldiphenylsilyloxy)-7-((naphthalen-2-ylmethoxy)methyl)non-1-en-4,5-diol

Base Information

• Chemical Name: (4S,5R,7R)-9-(tert-butyldiphenylsilyloxy)-7-((naphthalen-2-ylmethoxy)methyl)non-1-en-4,5-diol
• CAS No.: 1452373-19-1
• Molecular Formula: C₃₇H₄₆O₄Si
• Molecular Weight: 582.855
• Mol file: 1452373-19-1.mol

Synonyms:(4S,5R,7R)-9-(tert-butyldiphenylsilyloxy)-7-((naphthalen-2-ylmethoxy)methyl)non-1-en-4,5-diol

Chemical Property of (4S,5R,7R)-9-(tert-butyldiphenylsilyloxy)-7-((naphthalen-2-ylmethoxy)methyl)non-1-en-4,5-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R,7R)-9-(tert-butyldiphenylsilyloxy)-7-((naphthalen-2-ylmethoxy)methyl)non-1-en-4,5-diol

There total 11 articles about (4S,5R,7R)-9-(tert-butyldiphenylsilyloxy)-7-((naphthalen-2-ylmethoxy)methyl)non-1-en-4,5-diol 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: 83.0%

(4S,5R,7R)-9-(tert-butyldiphenylsilyloxy)-7-((naphthalen-2-ylmethoxy)methyl)-5-(trityloxy)non-1-en-4-ol (1452373-16-8) → (4S,5R,7R)-9-(tert-butyldiphenylsilyloxy)-7-((naphthalen-2-ylmethoxy)methyl)non-1-en-4,5-diol (1452373-19-1)

Guidance literature:

With boron trichloride; In dichloromethane; at -35 ℃; for 0.5h; Reagent/catalyst; Inert atmosphere;

DOI:10.3762/bjoc.9.132

Reference yield:

2-bromomethylnaphthyl bromide (939-26-4) → (4S,5R,7R)-9-(tert-butyldiphenylsilyloxy)-7-((naphthalen-2-ylmethoxy)methyl)non-1-en-4,5-diol (1452373-19-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride; tetra-(n-butyl)ammonium iodide; 1H-imidazole / tetrahydrofuran / 0 °C

2.1: Shi's ketone; oxone||potassium monopersulfate triple salt; tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate; potassium hydroxide; acetic acid; edetate disodium / acetonitrile; water / 9 h / 20 °C

3.1: copper(I) bromide dimethylsulfide complex; dimethylsulfide / tetrahydrofuran; diethyl ether / 1 h / -15 - 0 °C / Inert atmosphere

3.2: 18 h / 20 °C / Inert atmosphere

4.1: boron trichloride / dichloromethane / 0.5 h / -35 °C / Inert atmosphere

With 1H-imidazole; Shi's ketone; copper(I) bromide dimethylsulfide complex; dimethylsulfide; oxone||potassium monopersulfate triple salt; tetra(n-butyl)ammonium hydrogensulfate; edetate disodium; boron trichloride; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; acetic acid; potassium hydroxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetonitrile; 2.1: |Shi Asymmetric Epoxidation / 3.2: |Payne Rearrangement;

DOI:10.3762/bjoc.9.132

Reference yield:

C53H59NO4Si (1452372-81-4) → (4S,5R,7R)-9-(tert-butyldiphenylsilyloxy)-7-((naphthalen-2-ylmethoxy)methyl)non-1-en-4,5-diol (1452373-19-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: lithium amidotrihydridoborate / tetrahydrofuran / 0 - 20 °C

2.1: sodium hydride; tetra-(n-butyl)ammonium iodide; 1H-imidazole / tetrahydrofuran / 0 °C

3.1: Shi's ketone; oxone||potassium monopersulfate triple salt; tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate; potassium hydroxide; acetic acid; edetate disodium / acetonitrile; water / 9 h / 20 °C

4.1: copper(I) bromide dimethylsulfide complex; dimethylsulfide / tetrahydrofuran; diethyl ether / 1 h / -15 - 0 °C / Inert atmosphere

4.2: 18 h / 20 °C / Inert atmosphere

5.1: boron trichloride / dichloromethane / 0.5 h / -35 °C / Inert atmosphere

With 1H-imidazole; Shi's ketone; copper(I) bromide dimethylsulfide complex; lithium amidotrihydridoborate; dimethylsulfide; oxone||potassium monopersulfate triple salt; tetra(n-butyl)ammonium hydrogensulfate; edetate disodium; boron trichloride; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; acetic acid; potassium hydroxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetonitrile; 3.1: |Shi Asymmetric Epoxidation / 4.2: |Payne Rearrangement;

DOI:10.3762/bjoc.9.132

upstream raw materials:

C₃₀H₃₉NO₃Si

C₅₃H₅₉NO₄Si

C₄₃H₄₈O₃Si

2-bromomethylnaphthyl bromide