753488-75-4

Upstream product

• 753488-73-2 3α-benzoyloxy-4β,7α-dibenzyloxymethoxy-5α-cholan-24-oic acid 
• 3587-60-8 Benzyloxymethyl chloride 
• 753488-61-8 (R)-4-((7R,8S,9S,10R,13R,14S,17R)-7-Benzyloxymethoxy-4-hydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester 
• 610313-09-2 (R)-4-((7R,8S,9S,10R,13R,14S,17R)-4,7-Dihydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-pentanoic acid methyl ester 
• 65-85-0 benzoic acid 
• 14773-00-3 methyl (5β,7α)-12-hydroxy-3-oxo-cholan-24-oate 
• 610313-26-3 (R)-4-((3aS,5aR,5bS,7aR,8R,10aS,10bS,11R,12bR)-11-Benzyloxymethoxy-5a,7a-dimethyl-2-oxo-hexadecahydro-1,3-dioxa-2λ⁴-thia-dicyclopenta[a,i]phenathren-8-yl)-pentanoic acid methyl ester 
• 753488-70-9 methyl 3α-benzoyloxy-4β,7α-dibenzyloxymethoxy-5α-cholan-24-oate 
• 753488-67-4 Benzoic acid (3R,4R,5R,7R,8S,9S,10R,13R,14S,17R)-7-benzyloxymethoxy-4-hydroxy-17-((R)-3-methoxycarbonyl-1-methyl-propyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 
• 610313-13-8 methyl 7α-benzyloxymethoxy-3β,4β-cyclic sulfate-5α-cholan-24-oate 

Downstream Products

• 753488-78-7 3-α-benzoyloxy-4β,7α-dibenzyloxymethoxy-24-nor-5α-cholan-23-al 
• 753488-82-3 (25S)-4β,7α-dibenzyloxymethoxy-5α-cholest-23-ene-3α,26-diol 
• 753488-80-1 (25S)-4β,7α-dibenzyloxymethoxy-5α-cholest-23-ene-3α,26-diol 3α-benzoate 

Relevant academic research and scientific papers

Synthesis and identification of an endogenous sperm activating and attracting factor isolated from eggs of the ascidian Ciona intestinalis; An example of nanomolar-level structure elucidation of novel natural compound

A sperm-activating and attracting factor (SAAF) was isolated from the eggs of the ascidian Ciona intestinalis, and its structure was deduced with only approximately 4 μg of the specimen. Based upon the proposed structure, two epimers were synthesized from chenodeoxycholic acid in 16 steps. Comparison between synthetic and natural compounds led to the unambiguous structure determination of SAAF to be (3R,4R,7R,25S)-3,4,7,26-tetrahydroxycholestane-3,26- disulfate. The synthetic pure specimen was also utilized to confirm that both sperm-activation and attraction were elicited by a single compound.

Synthesis of endogenous sperm-activating and attracting factor isolated from ascidian Ciona intestinalis

A chemoattractant candidate named sperm-activating and attracting factor (SAAF) from the eggs of ascidian Ciona intestinalis, was synthesized from chenodeoxycholic acid in 16 steps. The present synthesis led to the unambiguous structure determination of SAAF to be (3R,4R,7R,25S)-3,4,7,26-tetrahydroxycholestane-3,26-disulfate. The synthetic pure specimen was also used to confirm the dual sperm-activating and attracting activity.