136379-61-8

Basic information

• Product Name: (2R,4aS,5S,8R,8aR)-5-{[tert-butyl(dimethyl)silyl]oxy}-8-hydroxy-4a,8-dimethyldecahydronaphthalen-2-yl methanesulfonate
• CAS NO: 136379-61-8
• Molecular Formula: C₁₉H₃₈O₅SSi
• Molecular Weight: 406.6525
• Mol File: 136379-61-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 472.3°C at 760 mmHg
• Flash Point: 239.4°C
• Density: 1.09g/cm³
• Vapor Pressure: 6.63E-11mmHg at 25°C
• Refractive Index: 1.496
• CAS DataBase Reference: (2R,4aS,5S,8R,8aR)-5-{[tert-butyl(dimethyl)silyl]oxy}-8-hydroxy-4a,8-dimethyldecahydronaphthalen-2-yl methanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,4aS,5S,8R,8aR)-5-{[tert-butyl(dimethyl)silyl]oxy}-8-hydroxy-4a,8-dimethyldecahydronaphthalen-2-yl methanesulfonate(136379-61-8)
• EPA Substance Registry System: (2R,4aS,5S,8R,8aR)-5-{[tert-butyl(dimethyl)silyl]oxy}-8-hydroxy-4a,8-dimethyldecahydronaphthalen-2-yl methanesulfonate(136379-61-8)

Safety Data

• Hazardous Substances Data: 136379-61-8(Hazardous Substances Data)

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 136379-64-1 (4α,4aα,8aβ)-4-[(tert-Butyldimethylsilyl)oxy]octahydro-7,7-dimethoxy-4a-methyl-1(2H)-naphthalenone 
• 144494-49-5 (1R,4S,4aS,8aS)-4-(tert-Butyl-dimethyl-silanyloxy)-7,7-dimethoxy-1,4a-dimethyl-decahydro-naphthalen-1-ol 
• 87262-05-3 4β-Hydroxy-4aβ-methyl-3,4,4a,5,6,8aα-hexahydronaphthalene-1(2H),7(8H)-dione 7-dimethyl acetal 
• 136379-65-2 (4aα,5α,8α,8aβ)-5-<(tert-Butyldimethylsilyl)oxy>octahydro-8-hydroxy-4a,8-dimethyl-2(1H)-naphthalenone 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 136379-62-9 (1α,4α,4aα,8aβ)-4-<(tert-Butyldimethylsilyl)oxy>-1,2,3,4,4a,5,6,8a-octahydro-1,4a-dimethyl-1-naphthalenol 
• 136379-69-6 (1α,4α,4aα,8aβ)-4-<(tert-Butyldimethylsilyl)oxy>-1,2,3,4,4a,5,8,8a-octahydro-1,4a-dimethyl-1-naphthalenol 

Relevant articles and documents

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

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.