136379-65-2 Usage
Uses
Used in Organic Synthesis:
(4aR,5R,8R,8aR)-5-[tert-butyl(dimethyl)silyl]oxy-8-hydroxy-4a,8-dimethyloctahydronaphthalen-2(1H)-one is used as an intermediate in organic synthesis for the production of various complex organic molecules. Its unique structure allows for selective functionalization and manipulation, making it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used as a Protecting Group in Organic Synthesis:
In the field of organic synthesis, (4aR,5R,8R,8aR)-5-{[tert-butyl(dimethyl)silyl]oxy}-8-hydroxy-4a,8-dimethyloctahydronaphthalen-2(1H)-one is used as a protecting group for hydroxyl groups. The tert-butyl(dimethyl)silyl group provides a stable and easily removable protecting group, which is crucial for the selective deprotection and further functionalization of the molecule. This application is particularly important in the synthesis of complex natural products and the development of new pharmaceutical agents.
Used in Chemical Reactions as a Reagent:
(4aR,5R,8R,8aR)-5-[tert-butyl(dimethyl)silyl]oxy-8-hydroxy-4a,8-dimethyloctahydronaphthalen-2(1H)-one also serves as a reagent in various chemical reactions, such as oxidation, reduction, and substitution reactions. Its unique structure and functional groups enable it to participate in a wide range of reactions, making it a useful tool for chemists in the development of new synthetic methods and the preparation of novel compounds.
Check Digit Verification of cas no
The CAS Registry Mumber 136379-65-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,6,3,7 and 9 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 136379-65:
(8*1)+(7*3)+(6*6)+(5*3)+(4*7)+(3*9)+(2*6)+(1*5)=152
152 % 10 = 2
So 136379-65-2 is a valid CAS Registry Number.
136379-65-2Relevant academic research and scientific papers
Base-Induced and -Directed Elimination and Rearrangement of Perhydronaphthalene-1,4-diol Monosulfonate Esters. Total Synthesis of (+/-)-Alloaromadendrane-4β,10α-diol and (+/-)-Alloaromadendrane-4α,10α-diol
Jenniskens, Louis H. D.,Wijnberg, Joannes B. P. A.,Groot, Aede de
, p. 6585 - 6591 (2007/10/02)
The total synthesis of (+/-)-alloaromadendrane-4β,10α-diol (1), supposedly isolated from Ambrosia peruviana Willd., is described.The strategically positioned axial hydroxyl group at C(4) played a crucial role in the two key steps of this synthesis (2 and 11 -> 3; 4 -> 5).Upon treatment with sodium tert-amylate in refluxing toluene, both the mesylates 2 and 11 predominantly gave the olefin 3.A mechanism for this regioselective elimination is proposed.The double bond of 3 at C(6)-C(7) was used to introduce a dimethylcyclopropane ring at this position.The intramolecular base-induced rearrangement of 4 proceeded with high selectivity, again guided by the alkoxide at C(4).The resulting exo olefin 5 was converted into diol 1, but its spectral data did not agree with those reported for the natural diol.The epimeric (+/-)-alloaromadendrane-4α,10α-diol (23) was prepared from 5 via a dehydratation, epoxidation, reduction sequence.Now the spectral data of the natural and the synthetic diol agreed very well and a revision of the structure of the natural product is postulated.
