(E)-(20S,25S)-20,23-Diacetyl-5β-furost-22-ene-3β,26-diyl diacetate

Meza‐Reyes, Socorro; Montiel‐Smith, Sara; Sandoval‐Ramírez, Jesús; Bernès, Syl­vain; Hernández-Linares, Guadalupe; Santillán, Rosa; Rincón, Susana

doi:10.1107/s1600536804013443

Cited by 1 publication

(2 citation statements)

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“…The acetyl group substituting the furostenic atom C23 forms a s-cis α,β-unsaturated ketone system with the E configuration at the C22?C23 double bond. The methyl group C21 is placed on the α steroidal face, in agreement with a general rule followed by furostenes: the bulkier group at C20 avoids steric hindrance with groups substituting C23 (Meza-Reyes et al, 2004). The solid-state conformation of the title compound is retained in solution, as confirmed by NMR data.…”

Section: Data Collectionsupporting

confidence: 67%

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(E)-(25S)-23-Acetyl-5β-furost-22-ene-3β,26-diol

Linares¹,

Ramírez

Meza‐Reyes

et al. 2008

Acta Cryst E

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The title steroid, C29H46O4, is a furostene derivative with a C=C double-bond length of 1.353 (3) Å and an E configuration. The side chain is oriented toward the α face of the A–E steroidal nucleus and presents a disordered terminal CH2—OH group [occupancies for resolved sites are 0.591 (9) and 0.409 (9)]. The methyl group at C20 attached to ring E is also oriented toward the α face, avoiding steric hindrance with the carbonyl O atom of the acetyl group. The furostene and acetyl functionalities form an α,β-unsaturated ketone system, with an s-cis configuration. All hydroxy and carbonyl groups are involved in weak intermolecular hydrogen bonds. The absolute configuration was assigned from the synthesis.

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Section: Data Collectionsupporting

confidence: 67%

“…The diacetate of the title compound has been characterized by X-ray crystallography (Sandoval-Ramírez et al, 2003), as well as a related furost-22-ene derivate with the C20 site substituted by a methyl group and an acetyl group (Meza-Reyes et al, 2004).…”

Section: Related Literaturementioning

confidence: 99%