105539-78-4

Basic information

• Product Name: 6-Oxabicyclo[3.2.1]octan-7-one, 4-(benzoyloxy)-3-bromo-1-hydroxy-, (1R,3S,4S,5R)-
• CAS NO: 105539-78-4
• Molecular Formula: C14H13BrO5
• Molecular Weight: 341.158
• Mol File: 105539-78-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 6-Oxabicyclo[3.2.1]octan-7-one, 4-(benzoyloxy)-3-bromo-1-hydroxy-, (1R,3S,4S,5R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Oxabicyclo[3.2.1]octan-7-one, 4-(benzoyloxy)-3-bromo-1-hydroxy-, (1R,3S,4S,5R)-(105539-78-4)
• EPA Substance Registry System: 6-Oxabicyclo[3.2.1]octan-7-one, 4-(benzoyloxy)-3-bromo-1-hydroxy-, (1R,3S,4S,5R)-(105539-78-4)

Safety Data

• Hazardous Substances Data: 105539-78-4(Hazardous Substances Data)

Upstream product

• 32384-44-4 (1S,3R,4R,5R)-4,5-Benzylidenedioxy-1-hydroxycyclohexane-1,3-carbolactone 
• 100-52-7 benzaldehyde 
• 77-95-2 D-(-)-quinic acid 

Downstream Products

• 335417-41-9 methyl (3S,4S,5S)-5-allyl-3-azido-4-hydroxy-1-cyclohexene-1-carboxylate 
• 335418-35-4 methyl (3R,4R,5R)-4-(acetylamino)-3-isopropoxy-5-vinyl-1-cyclohexene-1-carboxylate 
• 335417-43-1 methyl (3S,4S,5S)-5-allyl-3-azido-4-[(methylsulfonyl)oxy]-1-cyclohexene-1-carboxylate 
• 335417-50-0 methyl (3R,4R,5S)-4-(acetylamino)-5-allyl-3-isopropoxy-1-cyclohexene-1-carboxylate 
• 335417-88-4 methyl (3R,4R,5R)-4-(acetylamino)-5-(2-hydroxyethyl)-3-isopropoxy-1-cyclohexene-1-carboxylate 
• 335417-13-5 (3R,4R,5S)-4-(acetylamino)-5-allyl-3-isopropoxy-1-cyclohexene-1-carboxylic acid 
• 335417-26-0 methyl (1S,3S,4R,5R)-3-allyl-4,5-dihydroxy-1-[(methylsulfonyl)oxy]cyclohexanecarboxylate 
• 335417-54-4 methyl (3R,4R,5S)-4-(acetylamino)-5-allyl-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate 
• 335417-83-9 methyl (3R,4R,5R)-4-(acetylamino)-5-(2,3-dihydroxypropyl)-3-isopropoxy-1-cyclohexene-1-carboxylate 
• 335417-35-1 methyl (1S,3S,4R,5R)-3-allyl-5-hydroxy-1,4-bis[(methylsulfonyl)oxy]cyclohexanecarboxylate 
• 335417-22-6 (1S,3S,4R,5R)-3-allyl-1-[(methylsulfonyl)oxy]-7-oxo-6-oxabicyclo[3.2.1]oct-4-yl benzoate 
• 335417-98-6 2-(trimethylsilyl)ethyl (3R,4R,5R)-4-(acetylamino)-3-isopropoxy-5-(2-oxoethyl)-1-cyclohexene-1-carboxylate 
• 335417-94-2 2-(trimethylsilyl)ethyl (3R,4R,5S)-4-(acetylamino)-5-allyl-3-isopropoxy-1-cyclohexene-1-carboxylate 
• 335417-29-3 (1R,2R,3S,5S)-3-allyl-2-hydroxy-5-(methoxycarbonyl)-5-[(methylsulfonyl)oxy]cyclohexyl benzoate 

Relevant articles and documents

Application of stereocontrolled aldol coupling to synthesis of segments of immunosuppressants FK-506 and rapamycin

The sector comprising C24-C34 of FK-506 containing five of the stereogenic centers in this macrolide was synthesized from (-)-quinic acid. Aldol coupling of the C24-C34 unit with a methyl ketone representing C20-C23 of FK-506 proceeded with complete Felkin stereoselectivity to afford the C20-C34 portion of the immunosuppressant. A chelate transition state invoking coordination of a lithium enolate with a trityl ether is proposed to explain this stereoselectivity. The strategy adopted for construction of the C26-C34 moiety of FK-506 was extended to the C34-C42 subunit of rapamycin. A Mukaiyama asymmetric anti-aldol coupling was used to set in place the vicinal diol functionality at C27,28 in the C26-C33 segment of this macrolide.

The synthesis and absolute configuration of mycosporins. A novel application of the Staudinger reaction

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