53139-42-7

Basic information

• Product Name: stigmasteryl tosylate
• Synonyms: stigmasteryl tosylate
• CAS NO: 53139-42-7
• Molecular Weight: 566.889
• Mol File: 53139-42-7.mol
• Article Data: 24

Chemical Properties

• CAS DataBase Reference: stigmasteryl tosylate(CAS DataBase Reference)
• NIST Chemistry Reference: stigmasteryl tosylate(53139-42-7)
• EPA Substance Registry System: stigmasteryl tosylate(53139-42-7)

Safety Data

• Hazardous Substances Data: 53139-42-7(Hazardous Substances Data)

Upstream product

• 32345-19-0 24-ethylcholesta-5,22-dien-3β-ol 
• 98-59-9 p-toluenesulfonyl chloride 
• 83-48-7 Stigmasterol 
• 83-48-7 stigmasterol 

Downstream Products

• 34428-91-6 acetate of 24-Nor-cholesta-5,22-diene-3b-ol 
• 281659-15-2 (22E)-5α,6α-epoxy-3β-tosyloxystigmast-22-ene 
• 1263469-78-8 5-(((S)-2-((1aR,3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethylhexadecahydrocyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)propyl)thio)-1-phenyl-1H-tetrazole 
• 1263469-80-2 5-(((S)-2-((1aR,3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethylhexadecahydrocyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)propyl)sulfonyl)-1-phenyl-1H-tetrazole 
• 1263469-87-9 (3α,5R,6β,22E,24S)-24-benzyloxy-6-methoxy-3,5-cyclocholest-22-ene 
• 1263469-89-1 (3α,5R,6β,22Z,24R)-24-benzyloxy-6-methoxy-3,5-cyclocholest-22-ene 
• 1263469-88-0 (3α,5R,6β,22E,24R)-24-benzyloxy-6-methoxy-3,5-cyclocholest-22-ene 
• 25819-77-6 (20S)-6β-methoxy-3α,5-cyclo-5α-pregnane-20-carbaldehyde 
• 55064-56-7 6β-methoxy-3α,5-cyclo-22(R),23(S)-methylenecholestan-24-one 
• 10453-25-5 iso-stigmasteryl methyl ether 
• 53603-94-4 stigmasterol methyl ether 
• 51231-23-3 3α,5-cyclo-22-hydroxy-5α-23,24-bisnorcholan-6β-ol 6-methyl ether 
• 38788-81-7 (22E)-24-norcholesta-5,22-dien-3β-ol 
• 54278-89-6 occelasterol 

Relevant articles and documents

New Synthesis of Castasterone

An improved synthesis that could produce gram quantities of castasterone was proposed. The starting material was stigmasterol, the cyclic part of which was transformed in the first synthetic step into the 3α,5-cyclo-6-ketone. The side-chain carbon skeleton in the target compound was constructed with the required stereochemistry of the C-24 methyl via addition of methylacetylene, hydrogenation of the propargyl alcohol over Lindlar catalyst, and Claisen rearrangement. Diols were introduced using Sharpless asymmetric dihydroxylation of the intermediate ?2,22-dienone in the presence of (DHQD)2AQN. A unique feature of the synthesis was the avoidance of chromatographic separations of propargyl alcohols with similar chromatographic mobilities because the C-22 diastereomers were enriched in subsequent redox reactions.

Formal Semisynthesis of Demethylgorgosterol Utilizing a Stereoselective Intermolecular Cyclopropanation Reaction

In this study, we report a convenient and high yielding formal semisynthesis of demethylgorgosterol, a marine steroid with an intriguing sidechain containing a cyclopropane unit. This was achieved through the synthesis of an advanced ketone intermediate.

Practical and facile route to a functional intermediate from stigmasterol for the synthesis of 1α-hydroxyvitamin D5 and related compounds

As a functional and versatile intermediate for the synthesis of 1α-hydroxyvitamin D5 and related compounds, 1α,2α-epoxy-3β-hydroxystigmasta-5,7-diene was synthesized by a practical and facile 17-step route from stigmasterol in 17% overall yield.