39968-95-1

Basic information

• Product Name: 2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]corey lactone
• 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
• CAS NO: 39968-95-1
• Molecular Formula: C₁₄H₂₆O₄Si
• Molecular Weight: 286.43934
• Mol File: 39968-95-1.mol

Chemical Properties

• Appearance: /
• Density: 1.07
• CAS DataBase Reference: 2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]corey lactone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]corey lactone(39968-95-1)
• EPA Substance Registry System: 2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]corey lactone(39968-95-1)

Safety Data

• Hazardous Substances Data: 39968-95-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]corey lactone is used as a protecting group in organic synthesis for hydroxyl groups, ensuring that these groups remain intact and unreacted during complex chemical reactions. This application is crucial for the successful synthesis of target molecules with specific functional groups.
Used in Chemical Research:
In the field of chemical research, 2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]corey lactone serves as a valuable compound for studying the properties and reactivity of lactones and their derivatives. Its unique structure, including the TBDMS group, allows researchers to explore novel reaction pathways and develop innovative synthetic strategies.
Used in Pharmaceutical Industry:
2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]corey lactone is used as an intermediate in the synthesis of pharmaceutical compounds, particularly those containing lactone moieties. Its stability and reactivity make it suitable for the development of new drugs with potential therapeutic applications.
Used in Material Science:
In material science, 2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]corey lactone can be employed as a component in the design and synthesis of advanced materials, such as polymers and coatings, that exhibit specific properties due to the presence of the lactone ring and the TBDMS group.
Overall, 2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]corey lactone is a multifaceted compound with a wide range of applications across various industries, including organic synthesis, chemical research, pharmaceuticals, and material science, due to its unique structure and properties.

Upstream product

• 912445-64-8 (3aR,4S,5R,6aS)-5-(tert-butyldimethylsilyloxy)-4-(trityloxymethyl)-hexahydrocyclopenta(b)furan-2-one 
• 101208-17-7 (3aR,4S,5R,6aS)-5-(benzoyloxy)hexahydro-4-[(triphenylmethoxy)methyl]-2H-cyclopenta[b]furan-2-one 
• 39746-00-4 (1S,5R,6S,7R)-7-benzoyloxy-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-3-one 
• 62939-85-9 (-)-7α-hydroxy-6β-triphenylmethoxymethyl-cis-2-oxabicyclo<3.3.0>octan-3-one 
• 117624-93-8 (1S,5R,6R,7R)-6-<<(tert-butyldimethylsilyl)oxy>methyl>-7-<(tert-butyldimethylsilyl)oxy>-2-oxabicyclo<3.3.0>octane-3-one 
• 32233-40-2 (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 57930-46-8 (1S,5R,6R,7R)-(-)-6-acetoxymethyl-7-hydroxy-2-oxabicyclo<3.3.0>octan-3-one 
• 64091-14-1 (3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-2-oxohexahydro-2H-cyclopenta[b]furan-4-carbaldehyde 

Downstream Products

• 26198-80-1 (Z)-9-((1R,2S,3R)-3-hydroxy-2-((S,E)-3-hydroxyoct-1-en-1-yl)-5-oxocyclopentyl)non-7-enoic acid 
• 57944-39-5 (Z)-9-((1R,2S,3R,5S)-3,5-dihydroxy-2-((S,E)-3-hydroxyoct-1-en-1-yl)cyclopentyl)non-7-enoic acid 
• 551-11-1 dinoprost 

Relevant articles and documents

Synthetic method of bimatoprost

The invention relates to a synthetic method of bimatoprost, and belongs to the technical field of chemical synthesis. According to the method, doxazosin is synthesized by adopting the following synthesis route different from the conventional technology, s

Synthesis method of carboprost and tretrel carprost

The invention relates to a synthesis method of carboprost and tretrel carprost. According to the synthesis method of the carboprost, Corey lactone which is low in price and easy to obtain serves as the initial raw matrial, the carboprost is synthesized through the seven-step reaction, operation is convenient, intermediates are stable, environmental protection and economical performance are realized, and reaction is easy to control. Compared with the prior art, the synthesis method has the advantages that when the intermediates are synthesized, no isomers can be generated, products are easy toseparate, the yield of the end product (carboprost) is high, the novel more effective method is provided for the artificial synthesis of the carboprost, and the method can also be used for simple andhigh-yield synthesis of related carboprost derivatives such as tretrel carprost.

Stereoselective preparation of key intermediates for the synthesis of iso-, neuro- and phyto-prostane family members: Inaugural asymmetric synthesis of 17-E2c-dihomo- and 17-F2c-dihomo-isoprostanes

A practical methodology for the synthesis of key intermediates for isoprostane, neuroprostane and dihomo-isoprostane preparation has been described. The key strategy involved a three stage C-12 stereocenter inversion of the configuration of a Corey lacton

Novel synthetic approach to alfaprostol key intermediates via Stille coupling with an alkyne

Novel intermediates based on the Corey skeleton for preparation of the ω-chain of non-halogenated unnatural prostaglandin analogues containing a triple bond at position 13–14 (PG numbering) were synthesized. The utilization of a novel synthetic approach towards a new tin intermediate, and subsequent Stille coupling opens up new possibilities for preparing these important pharmaceutical intermediates.

Stereospecific Synthesis of Fluoroalkenes by Silver-Mediated Fluorination of Functionalized Alkenylstannanes

The known procedures for the conversion of alkenylstannanes into the corresponding fluoroalkenes suffer from largely variable yields and a limited compatibility with functional groups; most notably, protodestannation becomes a serious issue whenever protic sites are present in the substrate. Outlined in this paper is a convenient alternative with a much improved application profile, which is largely unperturbed by free alcohols and amides of all sorts. Key to success is the use of F-TEDA-PF6in combination with non-hygroscopic and bench-stable silver phosphinate (AgOP(O)Ph2) that acts as an essentially neutral, non-nucleophilic promotor and effective tin-scavenger at the same time. This new method opens many opportunities for late-stage fluorination of elaborate compounds far beyond the scope of the literature procedures, as witnessed by the preparation of a fluorinated macrolide antibiotic, a fluorinated prostaglandin derivative, and a set of fluorinated amino acid surrogates and peptide isosteres.

A synthetic Corey Lactone 3 - TBS method (by machine translation)

The present invention relates to the technical field of prostaglandins synthesis of compounds, in particular to a synthetic Corey Lactone 3 - TBS new method. In particular, in order to Corey Lactone as raw materials, firstly silicon ether base protection, then selectively remove primary alcohol TBS protecting group, so as to obtain the Corey Lactone 3 - TBS. The mild reaction conditions used in this invention, the operation is simple, and cheap raw material, without adverse effects to the environment, is suitable for mass production. (by machine translation)

Effect of allylic and homoallylic substituents on cross metathesis: syntheses of prostaglandins F2α and J2

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