77086-38-5

Usage

Uses

Used in Organic Synthesis:
1-(TERT-BUTYLDIMETHYLSILYLOXY)-1is used as a building block for the construction of complex organic molecules, providing a stable and easily modifiable platform for the attachment and manipulation of various functional groups.
Used as a Protecting Group for Alcohols:
In chemical reactions, 1-(TERT-BUTYLDIMETHYLSILYLOXY)-1serves as a protecting group for alcohols, preventing unwanted side reactions and ensuring the selective modification of other functional groups within the molecule.
Used in Pharmaceutical Intermediates Synthesis:
1-(TERT-BUTYLDIMETHYLSILYLOXY)-1is utilized in the synthesis of pharmaceutical intermediates, where its protective properties and reactivity are leveraged to create molecules with specific biological activities.
Used in Drug Development:
1-(TERT-BUTYLDIMETHYLSILYLOXY)-1contributes to the development of new drugs by enabling the synthesis of complex molecular structures with potential therapeutic applications.
Used in Material Science:
Its application extends to material science, where it aids in the creation of new materials with unique properties, thanks to its role in the synthesis of complex organic compounds.

InChI:InChI=1/C9H20O2Si/c1-8(10-5)11-12(6,7)9(2,3)4/h1H2,2-7H3

Upstream product

• 125606-54-4 (2S)-2-(phenylsulfinylmethyl)butanamide 
• 79-20-9 acetic acid methyl ester 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 109-72-8 n-butyllithium 
• 108-18-9 diisopropylamine 

Downstream Products

• 132925-06-5 methyl 3-(t-butyldimethylsilyloxy)-5-phenylpentanoate 
• 84784-67-8 C₂₂H₃₁NO₃Si 
• 125257-81-0 3-phenyl-5-(tert-butyldimethylsiloxy)-5-methoxyisoxazoline 
• 79293-84-8 N-(tert-butyldimethylsilyl)phthalimide 
• 344867-60-3 3-(tert-Butyl-dimethyl-silanyloxy)-4-phenyl-pentanoic acid methyl ester 
• 138879-08-0 methyl (1α,2α,3β)-2-(methoxycarbonyl)-3-<(methoxycarbonyl)methyl>cyclohexaneacetate 
• 138879-10-4 (1R,2S,6R)-2,6-Bis-methoxycarbonylmethyl-cyclohexanecarboxylic acid methyl ester 
• 138879-09-1 (1S,2R,6S)-2,6-Bis-methoxycarbonylmethyl-cyclohexanecarboxylic acid methyl ester 
• 137207-22-8 Cyano-(1-methoxycarbonylmethyl-cyclohexyl)-acetic acid ethyl ester 
• 113107-61-2 1-tert-butyldimethylsiloxyallyl phenyl sulfide 
• 113107-74-7 dimethyl 2-succinate 
• 113107-57-6 methyl 4-tert-butyldimethylsiloxy-4-(phenylthio)butanonate 
• 113107-63-4 methyl 4-tert-butyldimethylsiloxy-3-phenyl-4-(phenylthio)butanonate 
• 74262-67-2 methyl (3SR,4RS)-4-(benzyloxy)-3-hydroxypentanoate 

Relevant academic research and scientific papers

Nucleophilic Addition to Nitrones Using a Flow Microreactor

Nucleophilic addition reactions of soft carbon nucleophiles to nitrones in a flow microreactor are reported for the first time. Under microflow conditions at 30 to 0 °C, a range of nitrones can be efficiently transformed into the corresponding oxyiminium ions by reaction with either acyl halides or trialkylsilyl triflates. These can subsequently undergo the addition of nucleophiles including allyltributylstannane, ketene methyl tert-butyldimethylsilyl acetal, and N-silyl ketene imines to afford the corresponding adducts in high yields; such reactions at a similar temperature under batch conditions resulted in lower yields because of undesired side reactions.

Organocatalytic Enantioselective Mukaiyama–Mannich Reaction of Isatin-Derived Ketimines for the Synthesis of Oxindolyl-β3, 3-Amino Acid Esters

Mukaiyama–Mannich reactions of ester enolate equivalents with aldimines have been elegantly used for the asymmetric synthesis of β-amino acids; nevertheless, the corresponding asymmetric reaction employing ketimines are unexplored. Herein, the first organocatalytic enantioselective Mukaiyama–Mannich reaction employing isatin-derived ketimines with unsubstituted silyl ketene acetals is disclosed towards the scalable synthesis of 2-oxoindolinyl-β3, 3-amino acid esters at room temperature with excellent enantioselectivities (ee >99.5 %). Ultra-low catalyst loadings (as low as 250 ppm) could be used for the quantitative product formation with high enantiopurity. The synthetic utility of this protocol has been showcased in the short formal synthesis of pharmaceutically demanded (+)-AG-041R, a potent gastrin/CCK-B receptor antagonist.

Triflimide: An Overlooked High-Performance Catalyst of the Mukaiyama Aldol Reaction of Silyl Ketene Acetals with Ketones

The Mukaiyama aldol reaction is a widely applied carbon–carbon bond forming reaction. However, despite numerous well-established methods using aldehydes as acceptors, only few examples exist with ketones. Here we report a highly practical catalytic approach to this transformation, namely, the triflimide catalyzed Mukaiyama aldol reaction of silyl ketene acetals with ketones. This method exhibits a broad substrate scope, is very rapid, tolerates functionalized substrates, and requires only parts-per-million catalyst loadings with preparative scale reactions up to hundreds of grams in excellent purity (>99 %).

1,1,3,3-Tetratriflylpropene (TTP): A Strong, Allylic C–H Acid for Br?nsted and Lewis Acid Catalysis

Tetratrifylpropene (TTP) has been developed as a highly acidic, allylic C–H acid for Br?nsted and Lewis acid catalysis. It can readily be obtained in two steps and consistently shows exceptional catalytic activities for Mukaiyama aldol, Hosomi–Sakurai, an

Chiral helical oligotriazoles: New class of anion-binding catalysts for the asymmetric dearomatization of electron-deficient N -heteroarenes

Helical chirality and selective anion-binding processes are key strategies used in nature to promote highly enantioselective chemical reactions. Although enormous efforts have been made to develop simple helical chiral systems and thus open new possibilities in asymmetric catalysis and synthesis, the efficient use of synthetic oligo- and polymeric helical chiral catalysts is still very challenging and rather unusual. In this work, structural unique chiral oligotriazoles have been developed as C-H bond-based anion-binding catalysts for the asymmetric dearomatization of N-heteroarenes. These rotational flexible catalysts adopt a reinforced chiral helical conformation upon binding to a chloride anion, allowing high levels of chirality transfer via a close chiral anion-pair complex with a preformed ionic substrate. This methodology offers a straightforward and potent entry to the synthesis of chiral (bioactive)heterocycles with added synthetic value from simple and abundant heteroarenes.

Replacement of HMPA in samarium diiodide promoted cyclizations and reactions of organolithium compounds

Tripyrrolidinophosphoric acid triamide (TPPA) can replace carcinogenic HMPA as a Lewis basic additive in many reactions involving samarium ketyls. In most cases, yields and selectivities of cyclizations of (het)aryl, alkenyl, and alkynyl ketones are simil

Asymmetric catalytic Mannich reactions catalyzed by urea derivatives: Enantioselective synthesis of β-aryl-β-amino acids

Highly enantioselective addition reactions between silyl ketene acetals and N-Boc aldimines are catalyzed by the thiourea-based catalyst 1c. Extraordinary scope is observed in this methodology with regard to the imine substrate, with aryl and heteroaromatic derivatives generally affording nearly quantitative yields of β-amino ester product in up to 98% enantioselectivity. Copyright

Chemistry of O-silylated ketene acetals: A stereoselective synthesis of optically active carbapenem antibiotics, (+)-thienamycin and (+)-PS-5

A stereoselective synthesis of the chiral thienamycin intermediate (16) involving a diastereoselective Michael addition and a silicon-induced Pummerer-type reaction is described. In a similar way, the key intermediate for (+)-PS-5 was also prepared from 4

Acyclic Stereoselection. 36. Simple Diastereoselection in the Lewis Acid Mediated Reactions of Enol Silanes with Aldehydes

The Lewis acid mediated aldol reactions of enol silanes with aldehydes have been investigated.The effects of enol silane structure, both nature of the ligand at the silyloxy carbon and the geometry of the double bond, the aldehyde structure, and the nature of the Lewis acid have been studied.In general, the reactions of prochiral enol silanes with prochiral aldehydes show little simple diastereoselection (Table I).An exception is Z enol silane 7, derived from ethyl tert-butyl ketone, which shows synthetically useful anti selectivity.Enol silane 36 may therefore be used as an anti-selective propionate equivalent.The chiral α-alkoxy aldehyde 43 shows a high diastereofacial preference in its reactions with enol silanes 42c and 42d provided a Lewis acid capable of expanding its coordination beyond four is used (TiCl4 or SnCl4) (Table II).However, with the related ketene acetal 41b, only modest diastereofacial selectivity is seen (Table II).Aldehyde 43 also shows a high diastereofacial preference, in the chelation-controlled sense, in its reactions with prochiral enol silanes 5-9.However, the simple diastereoselection observed in the latter reactions (Table III) is quite different from that observed in the reactions of prochiral aldehydes with the same enol silanes.For example, enol silane 7, which shows good anti selectivity in its reactions with prochiral aldehydes, gives a 15:1 mixture of the two syn aldols in its reaction with 43; while the reverse is true with the propiophenone-derived enol silanes 8 and 9.Finally, the results obtained in this study, along with those reported by other investigators, have been formulated into a coherent mechanistic rationale involving open transition states of the sort depicted in Figures 1 and 3.

Keten Silyl Acetal Chemistry; Simple Synthesis of Methyl Jasmonate and Related Compounds by Utilising Keten Methyl Dimethyl-t-butylsilyl Acetal

Conjugate addition of keten silyl acetals to α,β-unsaturated carbonyl compounds in acetonitrile gave a quantitative yield of the corresponding methyl (3-trialkylsiloxyalk-2-enyl)acetates; subsequent site-specific electrophilic substitution yielded the corresponding 2-substituted 3-(alkoxycarbonylmethyl)alkanones.These novel addition and sequential alkylation reactions could be applied to a simple synthesis of methyl jasmonate, methyl didehydrojasmonate, and methyl dihydrojasmonate.