220235-68-7

Upstream product

• 27871-49-4 (S)-Methyl lactate 
• 220235-77-8 4-methoxybenzyl-2-pyridylthio carbonate 
• 89238-99-3 O-(4-methoxybenzyl)-trichloroacetimidate 
• 105-13-5 4-Methoxybenzyl alcohol 
• 824-94-2 p-methoxybenzyl chloride 

Downstream Products

• 229647-61-4 (S)-2-((4-methoxybenzyl)oxy)propanoic acid 
• 126361-27-1 (S)-(p-methoxybenzyloxy)propanal 
• 214892-50-9 (4S,5S)-4-hydroxy-5-(4-methoxybenzyloxy)-1-hexene 
• 122151-36-4 (S)-2-O-(4'-methoxybenzyl)propan-1,2-diol 
• 917839-04-4 (S)-dimethyl 3-(4-methoxybenzyloxy)-2-oxobutylphosphonate 
• 332837-94-2 (S)-2-(4-methoxybenzyloxy)propanoyl chloride 
• 332837-95-3 (3R,4S)-4-((E)-2-Iodo-propenyl)-1-[(S)-2-(4-methoxy-benzyloxy)-propionyl]-3-methyl-azetidin-2-one 
• 861902-93-4 (S)-N-methoxy-2-((4-methoxybenzyl)oxy)-N-methylpropanamide 
• 1058681-56-3 (S)-3-((4-methoxybenzyl)oxy)butan-2-one 
• 1058681-93-8 (2S,5S)-5-hydroxy-2-((4-methoxybenzyl)oxy)-6-methylhept-6-en-3-one 
• 1415121-62-8 (2S,5R)-5-hydroxy-2-((4-methoxybenzyl)oxy)-6-methylhept-6-en-3-one 
• 1058681-85-8 (2S,5S)-5-hydroxy-2-((4-methoxybenzyl)oxy)-6-methylheptan-3-one 
• 1415121-54-8 (2S,5R)-5-hydroxy-2-((4-methoxybenzyl)oxy)-6-methylheptan-3-one 
• 1415121-60-6 (2S,5S)-5-hydroxy-2-((4-methoxybenzyl)oxy)heptan-3-one 

Relevant academic research and scientific papers

INHIBITORS OF INDOLEAMINE 2,3-DIOXYGENASE AND METHODS OF THEIR USE

The present invention provides a compound of formula (II): an inhibitor of indoleamine 2,3-dioxygenase (IDO), which may be used as medicaments for the treatment of proliferative disorders, such as cancer, viral infections and/or autoimmune diseases. Its prodrugs are disclosed.

Polyoxygenated Tertiary Alcohols: A Kiyooka Approach

A Kiyooka aldol approach for the stereoselective synthesis of tertiary alcohols is presented. This approach allows for the incorporation of different substituents at all three remaining positions at the chiral center bearing the tertiary alcohol. To demon

Diastereoselectivity in the boron aldol reaction of α-alkoxy and α,β-bis-alkoxy methyl ketones

In this work, using DFT calculations, we investigated the 1,4 and 1,5 asymmetric induction in boron enolate aldol reactions of α-alkoxy and α,β-bisalkoxy methyl ketones. We evaluated the steric influence of alkyl substituents at the α position and the stereoelectronic influence of the oxygen protecting groups at the α and β positions. Theoretical calculations revealed the origins of the 1,4 asymmetric induction in terms of the nature of the β-substituent. The synergistic effect between the α,β-syn and α,β-anti-bisalkoxy stereocenters was elucidated. In the presence of the β-alkoxy center, the reaction proceeds through the Goodman-Paton 1,5-stereoinduction model, experiencing a minor influence of the α-alkoxy center.

Stereodivergent approach in the protected glycal synthesis of L-vancosamine, L-saccharosamine, L-daunosamine and L-ristosamine involving a ring-closing metathesis step

In this paper, a new access to several chiral 3-aminoglycals as potential precursors for glycosylated natural products is reported from a common starting material, (?)-methyl-L-lactate. The stereodivergent strategy is based on the implementation of a ring

Structure determination and total synthesis of (+)-16-hydroxy-16,22- dihydroapparicine

Herein, we describe the first asymmetric total synthesis and determination of the relative and absolute stereochemistry of naturally occurring 16-hydroxy-16,22-dihydroapparicine. The key steps include 1) a novel phosphinimine-mediated cascade reaction to

Streamlined, asymmetric synthesis of 8,4′-oxyneolignans

Highly direct, modular syntheses of several natural 8,4′- oxyneolignans [(-)-1, (+)-1, (-)-2, and (-)-3] and some related variants [(-)-26, (+)-26, (+)-27, and (-)-28] are reported. Utilizing (S)- or (R)-methyl lactate as the chiral sources, two complementary syn- or anti-oriented routes were designed, encompassing nine and five steps, which were carried out to deliver the targets in an enantiomerically pure form. The embodiment of the two independent aryl and aryloxy moieties onto the lactate frame was performed according to a diversity-oriented protocol from the common precursors, aldehydes 6 and ent-6 for the syn-oriented routes and mesyl esters 19 and ent-19 for the anti-oriented routes. These syntheses set the stage for the generation of a wide and diverse repertoire of 8,4′-oxyneolignan compounds and the broad biological interrogation of its members.

Stereocontrolled route to vicinal diamines by [3.3] sigmatropic rearrangement of allyl cyanate: Asymmetric synthesis of anti-(2R,3R)- and syn-(2R,3S)-2,3-diaminobutanoic acids

(Diagram presented) A stereocontrolled route via allyl 1,2-diols to vicinal diamines based on the [3.3] sigmatropic rearrangement of allyl cyanate has been developed. Our approach consists of two consecutive steps: stereoselective construction of allyl an

Total synthesis of actinobolin from d-glucose by way of the stereoselective three-component coupling reaction

The total synthesis of (-)-actinobolin 3, an antipode of the natural product, starting from d-glucose is described. A three-component coupling reaction of functionalized cyclohexenone (+)-6 derived from d-glucose by way of Ferrier's carbocyclization react

Studies on the synthesis of landomycin A: Synthesis and glycosidation reactions of L-rhodinosyl acetate derivatives

An efficient, eight-step synthesis of L-rhodinosyl acetate derivative 3 is described. The synthesis originates from methyl (S)-lactate and involves a highly stereoselective, chelate-controlled addition of allyltributylstannane to the lactaldehyde derivative 7. The β-anomeric configuration of 3 was established with high selectivity by acetylation of the pyranose precursor with Ac2O and Et3N in CH2Cl2. Preliminary studies of glycosidation reactions of 3 and L-rhodinosyl acetate 10 containing a 3-O-TES ether revealed that these compounds are highly reactive glycosidating agents and that trialkylsilyl triflates are effective glycosylation promoters. The best conditions for reactions with 15 as the accepter involved use of diethyl ether as the reaction solvent and 0.2 equiv of TES-OTf at -78°C. However, the TES ether protecting group of 10 proved to be too labile under these reaction conditions, and mixtures of 16a, 17, and 18a are obtained in reactions of 10 and 15. Disaccharide 17 arises via in situ cleavage of the TES ether of disaccharide 16a, while trisaccharide 18a results from a glycosidation of in situ generated 17 (or of 16a itself) with a second equivalent of 10. These problems were largely suppressed by using 3 with a 3-O-TBS ether protecting group as the glycosyl donor and 0.2 equiv of TES-OTf as the reaction promoter. Attempts to selectively glycosylate the C(3)-OH of diol acceptors 20 or 28 gave a 70:30 mixture of 21 and 22 in the reaction of 20 and a 43:27:30 mixture of regioisomeric trisaccharides 29 and 30 and tetrasaccharide 31 from the glycosidation reaction of 28. However, excellent results were obtained in the glycosidation of differentially protected disaccharide 34 using 1.5 equiv of 3 and 0.05 equiv of TBS-OTf in CH2-Cl2 at -78°C. The latter step is an important transformation in the recently reported synthesis of the landomycin A hexasaccharide unit.

An approach to the total synthesis of lankacidins: Synthesis of advanced macrocyclic precursors

The macrocyclic tetraenes 11 and 19, possible precursors of lankacidin C 1, have been prepared using intramolecular Stille reactions to close the macrocyclic rings. The Stille precursor 10 was prepared by stereoselective acylation of the azetidinone 3 using the thioester 7. After reduction and deprotection, cyclisation gave the macrocyclic product 11 in 55% yield. Alternatively, the Boc-protected amino-ester 17 was prepared by ring-opening of the azetidinone, and cyclised to the macrocycle 19 in 48% yield.