7'-tert-ButyldiMethylsilyloxy-6',7'-dihydro-6'-hydroxy-4',6'-diMethyl-spiro[cyclopropane-1,5'-[5H]inden]-2'(3'H)-one

Base Information

• Chemical Name: 7'-tert-ButyldiMethylsilyloxy-6',7'-dihydro-6'-hydroxy-4',6'-diMethyl-spiro[cyclopropane-1,5'-[5H]inden]-2'(3'H)-one
• CAS No.: 955978-16-2
• Molecular Formula: C₁₉H₃₀O₃Si
• Molecular Weight: 334.531
• Mol file: 955978-16-2.mol

Synonyms:

Chemical Property of 7'-tert-ButyldiMethylsilyloxy-6',7'-dihydro-6'-hydroxy-4',6'-diMethyl-spiro[cyclopropane-1,5'-[5H]inden]-2'(3'H)-one

Chemical Property:

• Solubility.: Dichloromethane, Ethyl Acetate

Purity/Quality:

7''-tert-Butyldimethylsilyloxy-6'',7''-dihydro-6''-hydroxy-4'',6''-dimethyl-spiro[cyclopropane-1,5''-[5H]inden]-2''(3''H)-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Intermediate in the preparation of Acylfulvene, a class of antitumor agents that exert their cytotoxic effects by forming covalent adducts with DNA and proteins.

Technology Process of 7'-tert-ButyldiMethylsilyloxy-6',7'-dihydro-6'-hydroxy-4',6'-diMethyl-spiro[cyclopropane-1,5'-[5H]inden]-2'(3'H)-one

There total 7 articles about 7'-tert-ButyldiMethylsilyloxy-6',7'-dihydro-6'-hydroxy-4',6'-diMethyl-spiro[cyclopropane-1,5'-[5H]inden]-2'(3'H)-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: 69.0%

3-(tert-butyl-dimethyl-silanyloxy)-2-[1-(1-methyl-propa-1,2-dienyl)-cyclopropyl]-pent-4-yn-2-ol (1035807-76-1) → C19H30O3Si (955978-16-2)

Guidance literature:

In dimethyl sulfoxide; toluene; at 110 ℃; for 0.166667h;

DOI:10.1021/ja990426h

Reference yield:

1,1-diacetylcyclopropane (695-70-5) → C19H30O3Si (955978-16-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) t-BuLi

2: 97 percent / CeCl₃

3: 98 percent / Et₃N, DMAP

4: 54 percent / 3)>6

5: 95 percent / aq. K₂CO₃ / methanol

6: 69 percent / dimethylsulfoxide; toluene / 0.17 h / 110 °C

With dmap; cerium(III) chloride; hydrido(triphenylphosphine)copper(I) hexamer; tert.-butyl lithium; potassium carbonate; triethylamine; In methanol; dimethyl sulfoxide; toluene;

DOI:10.1021/ja990426h

Reference yield:

3-trimethylsilyl-1-[(1,1-dimethylethyl)dimethylsilyloxy]-2-propyne (83578-59-0) → C19H30O3Si (955978-16-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) t-BuLi

2: 97 percent / CeCl₃

3: 98 percent / Et₃N, DMAP

4: 54 percent / 3)>6

5: 95 percent / aq. K₂CO₃ / methanol

6: 69 percent / dimethylsulfoxide; toluene / 0.17 h / 110 °C

With dmap; cerium(III) chloride; hydrido(triphenylphosphine)copper(I) hexamer; tert.-butyl lithium; potassium carbonate; triethylamine; In methanol; dimethyl sulfoxide; toluene;

DOI:10.1021/ja990426h

upstream raw materials:

3-(tert-butyl-dimethyl-silanyloxy)-2-[1-(1-methyl-propa-1,2-dienyl)-cyclopropyl]-pent-4-yn-2-ol

1,1-diacetylcyclopropane

3-trimethylsilyl-1-[(1,1-dimethylethyl)dimethylsilyloxy]-2-propyne