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

Base Information

• Chemical Name: (-)-7α-triethylsilyloxy-6β-triethylsilyloxymethyl-cis-2-oxabicyclo<3.3.0>octan-3-one
• CAS No.: 128948-09-4
• Molecular Formula: C₂₀H₄₀O₄Si₂
• Molecular Weight: 400.706
• Mol file: 128948-09-4.mol

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

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

There total 1 articles about (-)-7α-triethylsilyloxy-6β-triethylsilyloxymethyl-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-triethylsilyloxymethyl-cis-2-oxabicyclo<3.3.0>octan-3-one (128948-09-4)

Guidance literature:

Multi-step reaction with 3 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

With pyridine; sulfuric acid; sodium; In methanol;

Reference yield:

(-)-7α-triethylsilyloxy-6β-triethylsilyloxymethyl-cis-2-oxabicyclo<3.3.0>octan-3-one (128948-09-4) → latanoprost (130209-82-4,145773-22-4,913258-34-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 4 h / -72 °C

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

2.2: 0.92 h / 5 °C

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

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

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

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

7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 16 h / 30 °C

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

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

With sodium tetrahydroborate; oxalyl dichloride; nickel(II) chloride hexahydrate; lithium hydroxide monohydrate; potassium tert-butylate; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; dichloromethane; tert-butyl methyl ether; water; acetone; 2.2: |Wittig-Horner Reaction / 6.1: |Wittig Olefination;

DOI:10.1007/s12039-015-0963-2

Reference yield:

(-)-7α-triethylsilyloxy-6β-triethylsilyloxymethyl-cis-2-oxabicyclo<3.3.0>octan-3-one (128948-09-4) → bimatoprost (155206-00-1)

Guidance literature:

Multi-step reaction with 7 steps

1: oxalyl dichloride; triethylamine / dichloromethane; dimethyl sulfoxide / 4 h / -72 °C / Inert atmosphere

2: lithium hydroxide monohydrate / tert-butyl methyl ether / 0.75 h / 5 °C / Inert atmosphere

3: Candida antarctica lipase B / aq. phosphate buffer / pH 7 - 7.5 / Inert atmosphere

4: diisobutylaluminium hydride / tetrahydrofuran / Inert atmosphere

5: potassium tert-butylate / tetrahydrofuran / 5 °C / Inert atmosphere

6: potassium carbonate / acetone / 16 h / 30 °C / Inert atmosphere

7: 25 °C / Inert atmosphere

With Candida antarctica lipase B; oxalyl dichloride; lithium hydroxide monohydrate; potassium tert-butylate; diisobutylaluminium hydride; potassium carbonate; triethylamine; In tetrahydrofuran; aq. phosphate buffer; dichloromethane; tert-butyl methyl ether; dimethyl sulfoxide; acetone; 1: |Swern Oxidation / 2: |Wittig-Horner Reaction / 5: |Wittig Olefination;

DOI:10.14233/ajchem.2017.20878

upstream raw materials:

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

Downstream raw materials:

latanoprost

C₄₄H₈₂O₅Si₃

bimatoprost

Refernces