103775-34-4

Basic information

• Product Name: (R)-2-[(1R,2S,3S,4R)-2-Formyl-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl ester
• Synonyms: (R)-2-[(1R,2S,3S,4R)-2-Formyl-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl ester
• CAS NO: 103775-34-4
• Molecular Weight: 282.38
• Mol File: 103775-34-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (R)-2-[(1R,2S,3S,4R)-2-Formyl-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-[(1R,2S,3S,4R)-2-Formyl-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl ester(103775-34-4)
• EPA Substance Registry System: (R)-2-[(1R,2S,3S,4R)-2-Formyl-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl ester(103775-34-4)

Safety Data

• Hazardous Substances Data: 103775-34-4(Hazardous Substances Data)

Upstream product

• 92590-56-2 [3R-(3α,3aβ,6β,6aβ,9b,9aα,9bβ)]-decahydro-3-hydroxy-3,8,9-trimethyl-naphtho-[1,8-bc]-pyran-2(3H)-one 
• 129145-25-1 (3aS,6R,6aS,9R,9aS,9bS)-3,6,9-Trimethyl-dodecahydro-benzo[de]chromen-9-ol 
• 80286-58-4 artemisinic acid 
• 85031-63-6 5α-hydroperoxy-amorph-5-en-12-oic acid methyl ester 
• 186581-53-3 diazomethane 
• 105250-95-1 (R)-2-[(1R,2S,3S,4R)-2-Formyl-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid 
• 129145-24-0 (3aS,6R,6aS,9aS,9bS)-3,6,9-Trimethyl-2,3,3a,4,5,6,6a,7,9a,9b-decahydro-benzo[de]chromene 
• 129145-26-2 Sodium; (R)-2-((1R,4R,4aS,7R,8S,8aS)-7,8-dihydroxy-4,7-dimethyl-decahydro-naphthalen-1-yl)-propionate 
• 93913-63-4 1α-Δ⁵-10α-methyl-7β-<2'β-(1'-benzyloxy)-propyl>-decalone-4 
• 93913-62-3 3(R)-methyl-6(S)-<1(R)-methyl-2-(phenylmethoxy)ethyl>-2(S)-(3-oxobutyl)cyclohexanone 
• 93913-64-5 1α,10α-methyl-7β-<2'β-(1'-benzyloxy)-propyl>-decalone-4 
• 84051-32-1 (2S,5R)-2-((R)-1-(benzyloxy)propan-2-yl)-5-methylcyclohexanone 
• 85031-59-0 dihydroartemisinic acid 
• 13834-07-6 (1R,5R)-2-(2-Hydroxy-1-methyl-ethyl)-5-methyl-cyclohexanol 

Downstream Products

• 63968-64-9 arteannuin (Qinghaosu) 
• 87322-20-1 (R)-2-[(1S,3S,4R)-2-[1-Methoxy-meth-(Z)-ylidene]-4-methyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid methyl ester 
• 87322-21-2 (R)-2-{(1S,3S,4R)-2-[1-Methoxy-meth-(Z)-ylidene]-4-methyl-3-[2-(2-methyl-[1,3]dithian-2-yl)-ethyl]-cyclohexyl}-propionic acid methyl ester 
• 106623-24-9 (R)-2-{(1R,2S,3S,4R)-2-Formyl-4-methyl-3-[2-(2-methyl-[1,3]dithian-2-yl)-ethyl]-cyclohexyl}-propionic acid methyl ester 

Relevant articles and documents

The role of the 12-carboxylic acid group in the spontaneous autoxidation of dihydroartemisinic acid

Three of the four steps in the slow spontaneous autoxidation of dihydroartemisinic acid to artemisinin ('ene-type' reaction of molecular oxygen with the Δ4,5 double bond, Hock cleavage of the resulting tertiary allylic hydroperoxide, oxygenation of the enol product from Hock cleavage and cyclization of the resulting vicinal hydroperoxyl-aldehyde to the 1,2,4-trioxane system of artemisinin) are shown to be assisted by the proximity of the 12-carboxylic acid functional group in dihydroartemisinic acid to the functional groups participating in these reactions.

TOTAL SYNTHESIS OF ARTEANNUIN AND DEOXYARTEANNUIN

Arteannuin 1 is a new sesquiterpene lactone containing a peroxide linkage and is an antimalarial principle isolated from Artemisia annua L. .R(+)-Citronellal 5 as a starting material for the total synthesis was converted into 11R(-)-methyl dihydroarteannuinate 12 in 14 steps.The key intermediate 4 was obtained from compound 12 in 5 steps.The introduction of hydroperoxide in 4 by photooxidation followed by acid treatment gave 1.Hydroxylation of 4 with osmium tetraoxide afforded deoxyarteannuin 2.