(-)-7α-triethylsilyloxy-6β-formyl-cis-2-oxabicyclo<3.3.0>octan-3-one

Base Information

• Chemical Name: (-)-7α-triethylsilyloxy-6β-formyl-cis-2-oxabicyclo<3.3.0>octan-3-one
• CAS No.: 128948-10-7
• Molecular Formula: C₁₄H₂₄O₄Si
• Molecular Weight: 284.428
• Mol file: 128948-10-7.mol

Synonyms:(-)-7α-triethylsilyloxy-6β-formyl-cis-2-oxabicyclo<3.3.0>octan-3-one

Chemical Property of (-)-7α-triethylsilyloxy-6β-formyl-cis-2-oxabicyclo<3.3.0>octan-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-7α-triethylsilyloxy-6β-formyl-cis-2-oxabicyclo<3.3.0>octan-3-one

There total 1 articles about (-)-7α-triethylsilyloxy-6β-formyl-cis-2-oxabicyclo<3.3.0>octan-3-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:

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one (26054-46-6) → (-)-7α-triethylsilyloxy-6β-formyl-cis-2-oxabicyclo<3.3.0>octan-3-one (128948-10-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / conc. sulfuric acid / 1.) 80 deg C, 5 h, 2.) RT, 12 h

2: 6.2 g / sodium / methanol / 0.5 h / 0 °C

3: 97 percent / pyridine / 1 h / 60 °C

4: 62 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.67 h / -60 °C

With pyridine; oxalyl dichloride; sulfuric acid; sodium; dimethyl sulfoxide; In methanol; dichloromethane;

Reference yield: 51.0%

dimethyl(2-oxo-4-phenylbutyl)phosphonate (41162-19-0) + (-)-7α-triethylsilyloxy-6β-formyl-cis-2-oxabicyclo<3.3.0>octan-3-one (128948-10-7) → C24H34O4Si

Guidance literature:

dimethyl(2-oxo-4-phenylbutyl)phosphonate; With triethylamine; lithium chloride; In tetrahydrofuran; at -15 - -5 ℃;

(-)-7α-triethylsilyloxy-6β-formyl-cis-2-oxabicyclo<3.3.0>octan-3-one; In tetrahydrofuran; for 1h;

Reference yield:

(-)-7α-triethylsilyloxy-6β-formyl-cis-2-oxabicyclo<3.3.0>octan-3-one (128948-10-7) → latanoprost (130209-82-4,145773-22-4,913258-34-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: lithium hydroxide monohydrate / tert-butyl methyl ether / 1 h / 20 °C

1.2: 0.92 h / 5 °C

2.1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / methanol / 3 h / 0 °C

3.1: triethylamine / dichloromethane / 5 h / 5 - 10 °C

4.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / -70 °C

5.1: potassium tert-butylate / tetrahydrofuran / 6 h / 5 °C

6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 16 h / 30 °C

7.1: triethylamine / dichloromethane / 6 h / 5 - 10 °C

8.1: acetic acid / water; tetrahydrofuran / 8 h / 30 °C

With sodium tetrahydroborate; nickel(II) chloride hexahydrate; lithium hydroxide monohydrate; potassium tert-butylate; diisobutylaluminium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; dichloromethane; tert-butyl methyl ether; water; acetone; 1.2: |Wittig-Horner Reaction / 5.1: |Wittig Olefination;

DOI:10.1007/s12039-015-0963-2

upstream raw materials:

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one

Downstream raw materials:

latanoprost

C₄₄H₈₂O₅Si₃

bimatoprost

Refernces