(9R,10S,13S,14R,17S)-10,13-Dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)-1,2,4,9,10,11,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolane]
[CAS# 5488-51-7]

Identification

• Classification: Organic raw materials >> Heterocyclic compound
• Name: (9R,10S,13S,14R,17S)-10,13-Dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)-1,2,4,9,10,11,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolane]
• Molecular Formula: C₂₅H₃₆O₄
• Molecular Weight: 400.55
• CAS Registry Number: 5488-51-7
• EC Number: 611-207-6
• SMILES: C[C@]12CC[C@@H]3C(=CC=C4[C@]3(CCC5(C4)OCCO5)C)[C@@H]1CC[C@@H]2C6(OCCO6)C

Properties

• Density: 1.2±0.1 g/cm³ Calc.^*
• Boiling point: 511.4±50.0 ºC 760 mmHg (Calc.)^*
• Flash point: 124.2±36.9 ºC (Calc.)^*
• Index of refraction: 1.572 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS09 Warning
• Hazard Statements: H410
• Precautionary Statements: P273-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410

Discovory and Applicatios

(9R,10S,13S,14R,17S)-10,13-Dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)-1,2,4,9,10,11,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2′-[1,3]dioxolane] is a synthetic steroidal derivative that belongs to the class of spiroketal-protected steroids. The compound features a cyclopenta[a]phenanthrene backbone, characteristic of natural steroids such as cholesterol, estradiol, and testosterone, and a spiro-fused 1,3-dioxolane ring attached at the 17-position. This structural modification plays a significant role in modifying the physicochemical properties and metabolic stability of the steroid core.

The compound is not a naturally occurring molecule but was developed as part of efforts in synthetic organic and medicinal chemistry to explore functionalized steroids. The introduction of the spiro[1,3]dioxolane moiety serves primarily as a protecting group for the 17-position hydroxyl or carbonyl functionality, commonly encountered in steroid hormones. This protective function is useful during multistep synthesis, where selective reactivity is necessary. Spiroketal derivatives such as this one are known to enhance steric hindrance and can improve the compound’s stability under acidic or basic conditions compared to unprotected counterparts.

The development and use of spiroketal-steroid derivatives like this compound have been well-documented in steroid chemistry literature dating back to the mid-20th century, as part of studies aimed at synthesizing analogs of natural hormones or corticosteroids. These analogs are often designed to investigate structure-activity relationships or to produce candidates with improved therapeutic profiles. The dioxolane ring can be removed under mild acidic conditions, regenerating the corresponding hydroxyl or carbonyl group at C17, allowing the compound to serve as a key intermediate in the synthesis of bioactive steroids.

This particular compound is used in the synthesis of functionalized derivatives of progesterone, androgens, and glucocorticoids. Such derivatives are valuable in pharmaceutical development, especially in designing steroid-based drugs with anti-inflammatory, contraceptive, or anticancer properties. The rigid spiro system can influence the compound’s binding affinity to steroid receptors or its resistance to metabolic degradation, depending on the target biological system and the substituents present elsewhere in the molecule.

In synthetic chemistry, spiroketal groups like the 1,3-dioxolane in this compound are often employed in protecting sensitive functionalities during complex transformations. Their formation is typically achieved by the acid-catalyzed reaction of ketones or aldehydes with 1,2- or 1,3-diols. In the case of steroid synthesis, 2-methyl-1,3-dioxolane formation at the 17-position is well-established as a means to temporarily mask reactive ketone or alcohol groups to avoid undesired side reactions.

Additionally, spiro derivatives of steroidal frameworks are of interest in structural studies using NMR and X-ray crystallography, as the rigid structure imposed by the spiro junction can facilitate analysis of conformation and stereochemistry. The defined stereocenters at positions 9, 10, 13, 14, and 17 correspond to the natural stereochemistry of many endogenous steroids, ensuring compatibility with enzymatic and receptor systems in later transformations or evaluations.

In summary, (9R,10S,13S,14R,17S)-10,13-Dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)-1,2,4,9,10,11,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2′-[1,3]dioxolane] is a synthetic spiroketal-protected steroid used as an intermediate in the synthesis of functionalized steroids. Its role in protecting the 17-position of the steroid nucleus makes it a valuable compound in steroid chemistry, facilitating the synthesis of pharmacologically active steroidal derivatives and supporting research into steroid structure-function relationships.