4H-Cyclopenta-1,3-dioxole-5-ethanol,2,2-diethyltetrahydro-,(3aR,6aS)-rel-(9CI)

Base Information

• Chemical Name: 4H-Cyclopenta-1,3-dioxole-5-ethanol,2,2-diethyltetrahydro-,(3aR,6aS)-rel-(9CI)
• CAS No.: 773148-29-1
• Molecular Formula: C₁₂H₂₂O₃
• Molecular Weight: 214.305
• Mol file: 773148-29-1.mol

Synonyms:4H-Cyclopenta-1,3-dioxole-5-ethanol,2,2-diethyltetrahydro-,(3aR,6aS)-rel-(9CI)

Chemical Property of 4H-Cyclopenta-1,3-dioxole-5-ethanol,2,2-diethyltetrahydro-,(3aR,6aS)-rel-(9CI)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4H-Cyclopenta-1,3-dioxole-5-ethanol,2,2-diethyltetrahydro-,(3aR,6aS)-rel-(9CI)

There total 5 articles about 4H-Cyclopenta-1,3-dioxole-5-ethanol,2,2-diethyltetrahydro-,(3aR,6aS)-rel-(9CI) 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:

(2E)-2,3,4,7-tetradeoxy-7-iodo-5,6-O-(1-ethylpropylidene)-D-ribo-hept-2-enitol (771569-68-7) → (3aR,5R,6aS)-2,2-Diethyl-5-vinyl-tetrahydro-cyclopenta[1,3]dioxole + (3aR,5S,6aS)-2,2-Diethyl-5-vinyl-tetrahydro-cyclopenta[1,3]dioxole + 2-((3aR,5S,6aS)-2,2-Diethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl)-ethanol (773148-29-1)

Guidance literature:

With methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide; In tetrahydrofuran; at -78 ℃; for 1.75h; Title compound not separated from byproducts.; visible light;

DOI:10.1016/j.tet.2004.06.099

Reference yield:

(2E)-2,3,4,7-tetradeoxy-7-iodo-5,6-O-(1-ethylpropylidene)-D-ribo-hept-2-enitol (771569-68-7) → 2-((3aR,5R,6aS)-2,2-Diethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl)-ethanol + 2-((3aR,5S,6aS)-2,2-Diethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl)-ethanol (773148-29-1)

Guidance literature:

With triethyl borane; tri-n-butyl-tin hydride; In hexane; toluene; at 20 ℃; for 4h;

DOI:10.1016/j.tet.2004.06.099

Reference yield:

pentan-3-one (96-22-0) → 2-((3aR,5S,6aS)-2,2-Diethyl-tetrahydro-cyclopenta[1,3]dioxol-5-yl)-ethanol (773148-29-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 35 percent / pTSA*H₂O / 24 h / 70 °C

2: 63 percent / DIBAL / toluene / 5 h / 0 °C

3: SmI₂; MeOH; HMPA / tetrahydrofuran / 1.75 h / -78 °C / visible light

With methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide; diisobutylaluminium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; toluene;

DOI:10.1016/j.tet.2004.06.099

upstream raw materials:

(2E)-2,3,4,7-tetradeoxy-7-iodo-5,6-O-(1-ethylpropylidene)-D-ribo-hept-2-enitol

pentan-3-one

tert-butyl (2E)-2,3,4,7-tetradeoxy-7-iodo-D-ribo-hept-2-enoate

(2E)-2,3,4,7-tetradeoxy-7-iodo-5,6-O-(1-ethylpropylidene)-D-ribo-hept-2-enoic acid tert-butyl ester