95452-06-5

Usage

Uses

Used in Organic Synthesis:
2-(TERT-BUTYLDIMETHYLSILYL)-1,3-DITHIANE is used as a precursor in the synthesis of acylsilanes. Its anion can undergo alkylation with electrophiles, providing a general synthesis route to these important compounds.
Used in Chemical Reactions:
The anion of 2-(TERT-BUTYLDIMETHYLSILYL)-1,3-DITHIANE can participate in various chemical reactions, making it a versatile building block in the synthesis of complex organic molecules.
Physical Properties:
2-(TERT-BUTYLDIMETHYLSILYL)-1,3-DITHIANE exhibits a boiling point of 115°C at 0.03mmHg and 124°C at 5mmHg, with a density of 1.010. These properties make it suitable for various applications in the chemical industry, including as a reagent or intermediate in the production of other organosilicon compounds.

Preparation

prepared by alkylation of 2-lithio-1,3-dithiane with t-butyldimethylsilyl chloride (eq 1).

InChI:InChI=1/C10H22S2Si/c1-10(2,3)13(4,5)9-11-7-6-8-12-9/h9H,6-8H2,1-5H3

Upstream product

• 505-23-7 1,3 dithiane 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 36049-90-8 2-lithio-1,3-dithiane 

Downstream Products

• 410077-59-7 (2S,4R)-1-{2-[(2S,4R)-5-Benzyloxy-2,4-bis-(tert-butyl-dimethyl-silanyloxy)-pentyl]-[1,3]dithian-2-yl}-4-(tert-butyl-dimethyl-silanyloxy)-6-methylene-octan-2-ol 
• 253431-90-2 (2S,4S)-1,5-Bis-{2-[(R)-3-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-[1,3]dithian-2-yl}-pentane-2,4-diol 
• 192047-48-6 (1R)-(1-benzyloxymethyl-2-[1,3]dithian-2-yl-ethoxy)-tert-butyl-dimethyl-silane 
• 201275-61-8 (S)-1-{2-[(2S,4R)-5-Benzyloxy-2,4-bis-(tert-butyl-dimethyl-silanyloxy)-pentyl]-[1,3]dithian-2-yl}-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propan-2-ol 
• 692730-44-2 (-)-N-((1R)-{2-[(2R,5S)-2,5-bis-(tert-butyldimethylsilyloxy)nonyl]-(1,3-dithian-2-yl)methyl}butyl)-4-methylbenzenesulfonamide 
• 1093413-40-1 C₂₉H₄₄O₃S₂Si 
• 1160697-64-2 C₂₂H₃₆O₃S₂ 
• 1178869-80-1 C₅₅H₈₈O₇S₆Si 
• 1178870-00-2 C₂₄H₂₈O₅ 
• 1178869-99-2 C₄₇H₈₂O₃S₄Si₃ 
• 1178869-97-0 C₇₁H₁₁₀O₈S₄Si₃ 
• 1178870-01-3 C₇₁H₁₁₀O₈S₄Si₃ 
• 1178869-90-3 C₆₆H₁₀₈O₇S₄Si₃ 

Relevant academic research and scientific papers

Kinetic Resolution of Acylsilane Cyanohydrins via Organocatalytic Cycloetherification

An asymmetric cyanation of acylsilanes involving the in-situ formation of chiral acylsilane cyanohydrins followed by their kinetic resolution via organocatalytic cycloetherification is described. The highly enantio- and diastereoselective cycloetherificat

The Rickiols: 20-, 22-, and 24-membered Macrolides from the Ascomycete Hypoxylon rickii

In preceding studies the neotropical ascomycete Hypoxylon rickii turned out to be a prolific source of new secondary metabolites, considering that we had obtained terpenoids with five different scaffolds along with a series of terphenyls. From the mycelial extracts of a 70 L scale fermentation of this strain we additionally isolated nine new macrolides (1–9) by RP-HPLC. The planar structures were elucidated by NMR spectroscopy complemented by HR-ESIMS. The relative configurations were assigned by J-based configuration analyses and confirmed by Kishi′s Universal Database. Subsequently, the absolute configurations were assigned by Mosher′s method using the shift analysis of a tetra-MTPA derivative. For rickiol A (1) and E (5) we observed transesterification of 20-membered ring structures to 22-membered isomers rickiol A2 (6) and E2 (7), and to 24-membered isomers rickiol A3 (8) and rickiol E3 (9), respectively. Cytotoxic effects and moderate antibiotic activity against Gram-positive bacteria were observed for 1–8 and 1–6 and 8, respectively. The total synthesis of rickiol E3 (9) established easier access to these compounds.

Access to skipped polyene macrolides through ring-closing metathesis: Total synthesis of the RNA polymerase inhibitor ripostatin B

Rip-Roaring! A convergent total synthesis of antibiotic ripostatin B was developed. A key step in the synthesis is a metathesis reaction allowing for a ring closure to the labile doubly skipped triene macrolide. Copyright

Anticancer agents from the Australian tropical rainforest: Spiroacetals EBC-23, 24, 25, 72, 73, 75 and 76

EBC-23, 24, 25, 72, 73, 75 and 76 were isolated from the fruit of Cinnamomum laubatii (family Lauraceae) in the Australian tropical rainforests. EBC-23 (1) was synthesized stereoselectively, in nine linear steps in 8% overall yield, to confirm the reported relative stereochemistry and determine the absolute stereochemistry. Key to the total synthesis was a series of Tietze - Smith linchpin reactions. The novel spiroacetal structural motif, exemplified by EBC-23 (1), was found to inhibit the growth of the androgen-independent prostate tumor cell line DU145 in the mouse model, indicating potential for the treatment of refractory solid tumors in adults.

Reductions, reductive alkylations, and intramolecular cyclizations of acyl silanes with samarium diiodide or tributyltin hydride

A series of acyl silanes including aliphatic-, aromatic-, and bis-acyl silanes, as well as the acyl silanes bearing other substituents such as a bromine atom and alkenyl, succinimide, and carbonyl groups, were prepared, and their reactions with samarium diiodide or tributylstannane were studied. The reactions of acyl silanes occurred in various manners such as reductions, reductive alkylations, intramolecular radical cyclizations, pinacol couplings, aldol reactions, and Tishchenko reactions, depending on the nature of substrates and reaction conditions. Acyl silanes were generally reduced to give the corresponding α-silyl alcohols without transfer of silyl groups. Intramolecular radical cyclizations of 5-hexenoyl silanes and 1-silyl-1,5-pentanedione were realized to give α-silyl cyclopentanols and 1,2-cyclopentanediol derivatives, respectively. On treatment with samarium diiodide in tetrahydrofuran, 1-(trimethylsilyl)-1,6-hexanedione underwent a pinacol coupling reaction in the presence of t-BuOH, whereas it underwent a Tishchenko reaction in the presence of MeOH. The Tishchenko reaction of 1-silyl-1,5-pentanedione gave a δ-silyl-δ-lactone. On treating with samarium diiodide, 1-(trimethylsilyl)-1,5-hexanedione and 1,5-bis(trimethylsilyl)-1,6-hexanedione, underwent, respectively, intramolecular aldol reactions.

Formylsilanes. Chemoenzymatic and Chemical Syntheses of the 2,4-Dinitrophenylhydrazones of These Apparently Air- and Water-Stable Compounds

Formylsilanes have long been reported to be notoriously unstable compounds.In fact, no formylsilane has been reported that was stable in air or in water nor are there any known hydrates, imines, or hydrazones of formylsilanes.We have found that monoamine

Photochemical Reactions; Photochemistry of Acylsilanes: 1. Siloxycarbene Formation versus γ-H-Abstraction

The syntheses and the photolyses of the acylsilane 1 and the corresponding methyl ketone 2 are described.On n,?*-excitation, the silyl ketone 1 as well as the methyl ketone 2 undergo a Norrish type II reaction involving γ-H-abstraction and fragmentation to the diene 12, and acetone (20) or the acylsilane 26, respectively.The methyl ketone 2, but not the acylsilane 1, isomerizes to cyclobutanols (21A-D).Additionally, compound 1 shows photochemical behavior typical of acylsilanes undergoing rearrangement to the siloxycarbene intermediate c.Insertion of c into the O-H-bond of the enol 28 leads to compound 13.Initial trapping of the siloxycarbene c by H2O, however, gives rise to the formation of compounds 16-18.As minor photolysis products of 1, the isomers 14 and (Z)-15 were formed; however, on vapor phase thermolysis (520o) of 1, compounds 14 and (E/Z)-15 were obtained in 92percent combined yield.To a small extent the acylsilane 1 also undergoes Norrish type I cleavage leading to the acid 19.