6885-40-1

Basic information

• Product Name: 20-oxopregn-5-en-3-yl 4-methylbenzenesulfonate
• CAS NO: 6885-40-1
• Molecular Formula: C₂₈H₃₈O₄S
• Molecular Weight: 470.6639
• Mol File: 6885-40-1.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 591.3°C at 760 mmHg
• Flash Point: 311.4°C
• Density: 1.2g/cm³
• Vapor Pressure: 5.87E-14mmHg at 25°C
• Refractive Index: 1.581
• CAS DataBase Reference: 20-oxopregn-5-en-3-yl 4-methylbenzenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: 20-oxopregn-5-en-3-yl 4-methylbenzenesulfonate(6885-40-1)
• EPA Substance Registry System: 20-oxopregn-5-en-3-yl 4-methylbenzenesulfonate(6885-40-1)

Safety Data

• Hazardous Substances Data: 6885-40-1(Hazardous Substances Data)

Usage

Type

Synthetic compound

Usage

Production of pharmaceuticals and hormonal therapies

Source

Derived from pregnenolone

Function

Key intermediate in synthesis of corticosteroids and sex hormones

Industry

Pharmaceutical industry

Application

Treatment of hormonal imbalances, inflammation, autoimmune disorders

Research

Development of new drug formulations and therapeutic treatments

Upstream product

• 1778-02-5 Pregnenolone acetate 
• 979-02-2 16-dehydropregnenolone acetate 
• 145-13-1 Pregnenolone 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 17307-33-4 (20R)-pregn-5-ene-3β,20-diol 3-(4-methylbenzenesulfonate) 
• 26360-40-7 3β-acetoxy-19-hydroxy-Δ5-pregnen-20-one 
• 511-26-2 pregnenolone methyl ether 
• 465-53-2 6β-hydroxy-3α,5α-cyclo-pregnan-20-one 
• 17307-34-5 20β-Acetoxy-3β-tosyloxy-Δ⁵-pregnen 

Relevant articles and documents

Photoinduced Molecular Transformations. Part 131. Synthesis of 18-Norsteroids, Deoxofukujusonorone and the Related Steroids, based on a Selective β-Scission of Alkoxyl Radicals as the Key Step

A new transformation of steroids into 18-norsteroids under mild conditions is described.The key step was a regioselective β-scission of the alkoxyl radicals generated by photolysis of the hypoiodite of 18-hydroxy-18,20α-epoxy steroids, prepared by photoly

Facile Access to Bridged Ring Systems via Point-to-Planar Chirality Transfer: Unified Synthesis of Ten Cyclocitrinols

Bridged ring systems are found in a wide variety of biologically active molecules including pharmaceuticals and natural products. However, the development of practical methods to access such systems with precise control of the planar chirality presents considerable challenges to synthetic chemists. In the context of our work on the synthesis of cyclocitrinols, a family of steroidal natural products, we herein report the development of a point-to-planar chirality transfer strategy for preparing bridged ring systems from readily accessible fused ring systems. Inspired by the proposed pathway for biosynthesis of cyclocitrinols from ergosterol, our strategy involves a bioinspired cascade rearrangement, which enabled the gram-scale synthesis of a common intermediate in nine steps and subsequent unified synthesis of 10 cyclocitrinols in an additional one to three steps. Our work provides experimental support for the proposed biosynthetic pathway and for the possible interrelationships between members of the cyclocitrinol family. In addition to being a convenient route to 5(10→19)abeo-steroids, our strategy also offers a generalized approach to bridged ring systems via point-to-planar chirality transfer. Mechanistic investigations suggest that the key cascade rearrangement involves a regioselective ring scission of a cyclopropylcarbinyl cation rather than a direct Wagner-Meerwein rearrangement.

Scalable Synthesis of Cyclocitrinol

A 10-step synthesis of the C25 steroid natural product cyclocitrinol from inexpensive, commercially available pregnenolone is reported. This synthesis features a biomimetic cascade rearrangement to efficiently construct the challenging bicyclo[4.4.1] A/B ring system, which enabled a gram-scale synthesis of the bicyclo[4.4.1] enone intermediate 18 in only nine steps. This work also provides experimental support for the biosynthetic origin of cyclocitrinol.