344798-32-9

Basic information

• Product Name: (6S)-6-[[tert-ButyldiMethylsilyloxy]-1,3,4,5,6,7-hexahydro-1-[(E)-[(1R,3aS,7aR)-octahydro-1-[(1S)-2-iodo-1-Methylethyl]-7a-Methyl-4H-inden-4-ylidene]Methyl]benzo[c]thiophene 2,2-Dioxide
• Synonyms: (6S)-6-[[tert-ButyldiMethylsilyloxy]-1,3,4,5,6,7-hexahydro-1-[(E)-[(1R,3aS,7aR)-octahydro-1-[(1S)-2-iodo-1-Methylethyl]-7a-Methyl-4H-inden-4-ylidene]Methyl]benzo[c]thiophene 2,2-Dioxide
• CAS NO: 344798-32-9
• Molecular Formula: C₂₈H₄₇IO₃SSi
• Molecular Weight: 618.73
• Product Categories: Chiral Reagents, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 344798-32-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (6S)-6-[[tert-ButyldiMethylsilyloxy]-1,3,4,5,6,7-hexahydro-1-[(E)-[(1R,3aS,7aR)-octahydro-1-[(1S)-2-iodo-1-Methylethyl]-7a-Methyl-4H-inden-4-ylidene]Methyl]benzo[c]thiophene 2,2-Dioxide(CAS DataBase Reference)
• NIST Chemistry Reference: (6S)-6-[[tert-ButyldiMethylsilyloxy]-1,3,4,5,6,7-hexahydro-1-[(E)-[(1R,3aS,7aR)-octahydro-1-[(1S)-2-iodo-1-Methylethyl]-7a-Methyl-4H-inden-4-ylidene]Methyl]benzo[c]thiophene 2,2-Dioxide(344798-32-9)
• EPA Substance Registry System: (6S)-6-[[tert-ButyldiMethylsilyloxy]-1,3,4,5,6,7-hexahydro-1-[(E)-[(1R,3aS,7aR)-octahydro-1-[(1S)-2-iodo-1-Methylethyl]-7a-Methyl-4H-inden-4-ylidene]Methyl]benzo[c]thiophene 2,2-Dioxide(344798-32-9)

Safety Data

• Hazardous Substances Data: 344798-32-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(6S)-6-[[tert-ButyldiMethylsilyloxy]-1,3,4,5,6,7-hexahydro-1-[(E)-[(1R,3aS,7aR)-octahydro-1-[(1S)-2-iodo-1-Methylethyl]-7a-Methyl-4H-inden-4-ylidene]Methyl]benzo[c]thiophene 2,2-Dioxide is used as an intermediate in the synthesis of Secalciferol (S211500), a metabolite of Vitamin D. Secalciferol has potential anti-inflammatory properties, making it a valuable compound in the development of new pharmaceuticals for the treatment of various inflammatory conditions.
Used in Vitamin D Research:
As an intermediate in the synthesis of Secalciferol, (6S)-6-[[tert-ButyldiMethylsilyloxy]-1,3,4,5,6,7-hexahydro-1-[(E)-[(1R,3aS,7aR)-octahydro-1-[(1S)-2-iodo-1-Methylethyl]-7a-Methyl-4H-inden-4-ylidene]Methyl]benzo[c]thiophene 2,2-Dioxide plays a crucial role in research related to Vitamin D and its metabolites. (6S)-6-[[tert-ButyldiMethylsilyloxy]-1,3,4,5,6,7-hexahydro-1-[(E)-[(1R,3aS,7aR)-octahydro-1-[(1S)-2-iodo-1-Methylethyl]-7a-Methyl-4H-inden-4-ylidene]Methyl]benzo[c]thiophene 2,2-Dioxide can be used to study the biological activities and potential therapeutic applications of Secalciferol and other Vitamin D-related compounds.
Used in Chemical Synthesis:
Due to its complex molecular structure, (6S)-6-[[tert-ButyldiMethylsilyloxy]-1,3,4,5,6,7-hexahydro-1-[(E)-[(1R,3aS,7aR)-octahydro-1-[(1S)-2-iodo-1-Methylethyl]-7a-Methyl-4H-inden-4-ylidene]Methyl]benzo[c]thiophene 2,2-Dioxide can also be used as a building block or starting material in the synthesis of other complex organic compounds. This makes it a valuable tool for chemists working in various fields, including materials science, pharmaceuticals, and agrochemicals.

Upstream product

• 50-14-6 Calciferol 
• 87680-65-7 (S)-3-[(1R,3aS,7aR)-7a-Methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidenemethyl]-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ⁶-benzo[c]thiophen-5-ol 
• 866453-60-3 3(S)-tert-butyldimethylsilyloxy-20(S)-formyl-9,10-secoprega-5,7(E),10⁽¹⁹⁾-triene 
• 170081-43-3 SO2-adduct of 3(S)-<(tert-butyldimethylsilyl)oxy>-9,10-secoergosta-5,7(E),10(19),22(E)-tetraene 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 344798-31-8 3(S)-<(tert-butyldimethylsilyl)oxy>-20(S)-(hydroxymethyl)-9,10-secopregna-5(Z),7(E),10(19)-triene SO2 adduct 

Downstream Products

• 58050-56-9 C₂₈H₄₄O₂ 
• 120707-37-1 24(S)-hydroxyvitamin D₂ 
• 147125-20-0 (1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-25-keto-9,10-seco-27-norcholesta-5(E),7(E),10(19)-triene 
• 147125-14-2 ethyl 3(S)-<(tert-butyldimethylsilyl)oxy>-9,10-seco-26,27-bisnorcholesta-5(E),7(E),10(19)-trien-25-oate 
• 147125-18-6 3(S)-<(tert-butyldimethylsilyl)oxy>-25-keto-9,10-seco-27-norcholesta-5(E),7(E),10(19)-triene 
• 170081-45-5 3(S)-<(tert-butyldimethylsilyl)oxy>-20(S)-(iodomethyl)-9,10-secopregna-5(E),7(E),10(19)-triene 

Relevant articles and documents

A stereospecific synthesis of 24(S)-hydroxyvitamin D2, a prodrug for 1α,24(S)-dihydroxyvitamin D2

This contribution describes the first stereospecific synthesis of 24(S)-hydroxyvitamin D2 (1), a metabolite of vitamin D2. This metabolite acts as a prodrug for 1α,24(S)-dihydroxyvitamin D2 (2), which is under development for treatment of various diseases characterized by cellular hyperproliferation. The key step of the synthesis involves the Wittig-Horner olefination of (S)-2,3-dimethyl-2-triethysilyloxybutyraldehyde (17) and a vitamin D2 phosphine oxide derivative (22). The synthesis of the requisite aldehyde started with the commercially available L-(+)-valine and was completed in seven steps. The vitamin D2 phosphine oxide derivative was synthesized in seven steps starting from vitamin D2.

Nickel-Mediated Conjugate Addition. Elaboration of Calcitriol from Ergocalciferol

A convenient method for introduction the side chain of the hormone calcitriol (3) was achieved by coupling the nickel(0) complex derived from ethyl acrylate with the C-22 iodides 15, 16, 27, and 30 to give the corresponding esters 18, 21, 28, and 23 in yields of 73-82percent.Iodide 15 was also coupled with the Ni(0) complex derived from methyl vinyl ketone.The C-22 iodides 15 and 27 were obtained from ergocalciferol (6) and the 1(S),3(R)-bis-(5E,7E)-ergocalciferol derivative 24, respectively, by selective ozonolysis of their SO2 adducts, followed by in situ reduction of the ozonides with NaBH4 and iodination of the derived alcohols 14 and 26 with I2/PPh3/imidazole.The triene iodide 16 was prepared by extrusion of SO2 from 15, while 30 was obtained from the corresponding alcohol 29.Extrusion of SO2 from 21 and 28 gave the 5(E),7(E)-trienes 18 and 23, respectively.The latter was also made from the former by C-1 hydroxylation with selenium dioxide followed by silylation with tert-butyldimethylsilyl chloride and chromatographic separation.Completion of the synthesis of 3 was accomplished by treating 23 with methylmagnesium bromide to give 31, followed by desilylation with n-Bu4NF and triplet-sensitized photoisomerization.Alternatively, 31 was photoisomerized to 33, desilylation of which gave 3.Alcohol 33 was also prepared by the reaction of the 5Z,7E-triene ester 34, which was obtained by the photoisomerization of 23, with methylmagnesium bromide.