2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]corey lactone

Base Information

• Chemical Name: 2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]corey lactone
• CAS No.: 39968-95-1
• Molecular Formula: C14H26O4Si
• Molecular Weight: 286.444
• Mol file: 39968-95-1.mol

Synonyms:2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]corey lactone;(3aR,4S,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

Chemical Property of 2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]corey lactone

Chemical Property:

• PSA: 55.76000
• Density: 1.07
• LogP: 2.32070

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]corey lactone

There total 12 articles about 2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]corey lactone 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: 98.0%

(3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-2-oxohexahydro-2H-cyclopenta[b]furan-4-carbaldehyde (64091-14-1) → (3aR,4S,5R,6aS)-5-[(tert-butyldimethylsilyl)oxy]-4-(hydroxymethyl)-hexahydro-2H-cyclopenta[b]furan-2-one (39968-95-1)

Guidance literature:

With methanol; sodium tetrahydroborate; at 0 ℃;

DOI:10.1039/c8ob00489g

Reference yield: 83.0%

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one (32233-40-2) + tert-butyldimethylsilyl chloride (18162-48-6) → (3aR,4S,5R,6aS)-5-[(tert-butyldimethylsilyl)oxy]-4-(hydroxymethyl)-hexahydro-2H-cyclopenta[b]furan-2-one (39968-95-1)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃; for 8h; Reagent/catalyst;

Reference yield: 58.0%

(1S,5R,6R,7R)-6-<<(tert-butyldimethylsilyl)oxy>methyl>-7-<(tert-butyldimethylsilyl)oxy>-2-oxabicyclo<3.3.0>octane-3-one (117624-93-8) → (3aR,4S,5R,6aS)-5-[(tert-butyldimethylsilyl)oxy]-4-(hydroxymethyl)-hexahydro-2H-cyclopenta[b]furan-2-one (39968-95-1)

Guidance literature:

With acetic acid; In tetrahydrofuran; water; at 20 ℃; for 15h; Inert atmosphere;

DOI:10.1002/chem.201605444

upstream raw materials:

(3aR,4S,5R,6aS)-5-(tert-butyldimethylsilyloxy)-4-(trityloxymethyl)-hexahydrocyclopenta(b)furan-2-one

(3aR,4S,5R,6aS)-5-(benzoyloxy)hexahydro-4-[(triphenylmethoxy)methyl]-2H-cyclopenta[b]furan-2-one

(1S,5R,6S,7R)-7-benzoyloxy-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-3-one

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

Downstream raw materials:

dinoprost

(Z)-9-((1R,2S,3R)-3-hydroxy-2-((S,E)-3-hydroxyoct-1-en-1-yl)-5-oxocyclopentyl)non-7-enoic acid

(Z)-9-((1R,2S,3R,5S)-3,5-dihydroxy-2-((S,E)-3-hydroxyoct-1-en-1-yl)cyclopentyl)non-7-enoic acid

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