324024-12-6

Basic information

• Product Name: (S)-2-[(S)-1-Hydroxy-2-(tetrahydro-pyran-2-yloxy)-propyl]-12-(4-methoxy-benzyloxy)-5-methoxymethoxy-dodecanoic acid methyl ester
• Synonyms: (S)-2-[(S)-1-Hydroxy-2-(tetrahydro-pyran-2-yloxy)-propyl]-12-(4-methoxy-benzyloxy)-5-methoxymethoxy-dodecanoic acid methyl ester
• CAS NO: 324024-12-6
• Molecular Weight: 568.748
• Mol File: 324024-12-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (S)-2-[(S)-1-Hydroxy-2-(tetrahydro-pyran-2-yloxy)-propyl]-12-(4-methoxy-benzyloxy)-5-methoxymethoxy-dodecanoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-[(S)-1-Hydroxy-2-(tetrahydro-pyran-2-yloxy)-propyl]-12-(4-methoxy-benzyloxy)-5-methoxymethoxy-dodecanoic acid methyl ester(324024-12-6)
• EPA Substance Registry System: (S)-2-[(S)-1-Hydroxy-2-(tetrahydro-pyran-2-yloxy)-propyl]-12-(4-methoxy-benzyloxy)-5-methoxymethoxy-dodecanoic acid methyl ester(324024-12-6)

Safety Data

• Hazardous Substances Data: 324024-12-6(Hazardous Substances Data)

Upstream product

• 76438-34-1 (S)-2-(tetrahydropyranyloxy)propanal 
• 322765-07-1 methyl (5S)-5-methoxymethoxy-12-p-methoxybenzyloxydodecanoate 
• 105192-33-4 6-<(4-methoxyphenyl)methoxy>hexan-1-ol 
• 244168-10-3 methyl (5R,6R)-6,7-dihydroxy-6,7-O-isopropylidene-5-methoxymethoxy-heptanoate 
• 322765-10-6 methyl (5R)-5-methoxymethoxy-6-oxohexanoate 
• 310396-80-6 1-(((6-bromohexyl)oxy)methyl)-4-methoxybenzene 
• 176485-60-2 (E)-3-((4R,5S,4'R)-2,2,2',2'-Tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-acrylic acid ethyl ester 
• 824-94-2 p-methoxybenzyl chloride 
• 79308-47-7 methyl (5R,6R)-6,7-O-isopropylidene-5,6,7-trihydroxy-heptanoate 
• 629-11-8 1,6-hexanediol 

Downstream Products

• 322765-08-2 (5S,3'S)-3-(3'-methoxymethoxy-10'-p-methoxybenzyloxydodecan-1'-yl)-5-methylfuran-2(5H)-one 

Relevant articles and documents

Enantioselective syntheses of monotetrahydrofuran annonaceous acetogenins tonkinecin and annonacin starting from carbohydrates

The total synthesis of two mono-THF acetogenins, tonkinecin (1) and annonacin (2), is reported in full detail. Terminal acetylene 3 prepared from D-glucono-δ-lactone and asymmetric dihydroxylation was employed as a common intermediate for both targets 1 and 2. Pd(0)-catalyzed coupling reaction of 3 with vinyl iodides 4 and 5, the chiral centers of which were taken from D-xylose and S-(-)-ethyl lactate, afforded enyne 26 and 27, respectively. Selective hydrogenation of 26 or 27 with diimide followed by removal of MOM ethers completed the synthesis of 1. A coupling reaction between the lithium derivative of 3 and epoxide 6 in the presence of boron trifluoride etherate gave 42. Both chiral centers in epoxide 6 were taken from L-ascorbic acid. Subsequent catalytic hydrogenation and MOM protection led to 43b. Introduction of the butenolide moiety by aldol condensation of protected S-lactal followed by cleavage of all MOM ethers completed the synthesis of 2.