139403-50-2

Upstream product

• 41998-65-6 (2R*,3R*)-3-methyl-4-pentyne-2-ol 
• 66186-46-7 (4R*,5R*)-4-methyl-5-hydroxy-2-hexynoic acid 
• 880766-70-1 2-((1R,2R)-2-Hydroxy-1-methyl-propyl)-cyclopropane-1,1-dicarboxylic acid dimethyl ester 
• 64-17-5 ethanol 
• 1666-13-3 diphenyl diselenide 
• 603040-99-9 (2S,3R)-3-(4-Methoxy-benzyloxy)-2-methyl-butyraldehyde 
• 880766-68-7 (+)-(3R,4R)-4-(4-methoxybenzyl)oxy-3-methylpent-1-ene 
• 880766-67-6 (-)-(2R,3R,4R)-4-(4-methoxybenzyl)oxy-3-methylpentane-1,2-diol 
• 880766-69-8 (2RS)-2-[(1R,2R-)-2-(4-methoxybenzyl)oxy-1-methylpropyl]cyclopropane-1,1-dimethyl dicarboxylate 
• 139301-76-1 (3S,4R,5R)-5-acetoxy-3-acetoxymethyl-4-methylhexanoic acid 
• 139301-87-4 (3S,4R,5R)-5-acetoxy-3-acetoxymethyl-4-methylhexanal 
• 139301-75-0 (2R,3R,4S)-2-acetoxy-4-(acetoxymethyl)-3-methyl-6-heptene 
• 139301-74-9 (3R,4R,5R)-dihydro-4,5-dimethyl-3-(2-propenyl)furan-2(3H)-one 
• 139301-86-3 (2R,3R,4S)-4-hydroxymethyl-3-methyl-6-hepten-2-ol 

Downstream Products

• 111194-17-3 Hydroxy-((4S,5R,6R)-2-hydroxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-acetic acid 2-trimethylsilanyl-ethyl ester 
• 111194-20-8 ((2R,4S,5R,6R)-2-Methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-oxo-acetic acid 2-trimethylsilanyl-ethyl ester 
• 129156-14-5 Benzoic acid (S)-((2R,4S,5R,6R)-2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-(2-trimethylsilanyl-ethoxycarbonyl)-methyl ester 
• 111194-18-4 (S)-Hydroxy-((2R,4S,5R,6R)-2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-acetic acid 2-trimethylsilanyl-ethyl ester 
• 111194-18-4 (R)-Hydroxy-((2R,4S,5R,6R)-2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-acetic acid 2-trimethylsilanyl-ethyl ester 
• 104432-03-3 (+/-)-benzoylselenopederic acid 
• 139301-90-9 C₄₄H₆₉NO₁₀SeSi 
• 139301-91-0 Benzoic acid (R)-({(S)-[(2S,4R,6R)-4-(tert-butyl-dimethyl-silanyloxy)-6-((S)-2,3-dimethoxy-propyl)-5,5-dimethyl-tetrahydro-pyran-2-yl]-methoxy-methyl}-carbamoyl)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester 
• 139301-91-0 7-O-benzoyl-13-O-(tert-butyldimethylsilyl)pederin 
• 139301-89-6 N-{(S)-[(2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((S)-2,3-dimethoxy-propyl)-5,5-dimethyl-tetrahydro-pyran-2-yl]-methoxy-methyl}-2-hydroxy-2-((2R,4R,5R,6R)-2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-acetamide 
• 139301-88-5 N-{(S)-[(2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((S)-2,3-dimethoxy-propyl)-5,5-dimethyl-tetrahydro-pyran-2-yl]-methoxy-methyl}-2-((4S,5R,6R)-5,6-dimethyl-4-phenylselanylmethyl-5,6-dihydro-4H-pyran-2-yl)-2-hydroxy-acetamide 
• 139301-85-2 N-{(S)-[(2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((S)-2,3-dimethoxy-propyl)-5,5-dimethyl-tetrahydro-pyran-2-yl]-methoxy-methyl}-2-((4S,5R,6R)-5,6-dimethyl-4-phenylselanylmethyl-5,6-dihydro-4H-pyran-2-yl)-2-oxo-acetamide 
• 302356-06-5 benzoic acid {6-[3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-propyl]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl}-(2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-methyl ester 
• 302355-96-0 benzoic acid {6-[3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-propyl]-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl}-(2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-methyl ester 

Relevant academic research and scientific papers

Convergent total synthesis of (+)-mycalamide A

The details of a convergent total synthesis of (+)-mycalamide A are descri7bed. Yb(OTf)3-TMSCl-catalyzed cross-aldol reaction conditions are used to synthesize the right segment of mycalamide A. In this reaction, an acid-sensitive aldehyde reacts with methyl trimethylsilyl dimethylketene acetal without epimerization to provide the desired aldol adduct. Additionally, a tetrahydropyran ring, which is the left segment of mycalamide A, is prepared using a novel one-pot δ-lactone formation methodology. Both segments are constructed from a common starting material, D-mannitol. These segments are then coupled in the presence of BuLi, and the functional groups are transformed to complete the synthesis of (+)-mycalamide A.

Synthetic studies on the pederin family of antitumour agents. Syntheses of mycalamide B, theopederin D and pederin

The synthesis of mycalamide B, theopederin D and pederin, which are antitumour agents was discussed. All three compounds were prepared from 6-lithio-2,3-dimethyl-4-phenylselenomethyl-3,4-dihydro-2H-pyran and 2-(3-chloropropyl)-3,3-dimethyl-3,4-dihydro-2H-pyran-4-one. Ground state conformational models were proposed to explain the stereoselectivity of the reactions. The absolute and relative stereochemistry of the compounds has been established by X-ray crystallography and NMR studies.

A synthesis of mycalamide B

Mycalamide B, a potent antitumour agent, was synthesised from cheap, readily available starting materials: ethyl lactate, ethyl isobutyrate, 4-chlorobutanal, and 4-chlorobutanoyl chloride. The trioxabicyclo[4.4.0]decane ring system was created by reaction of a methoxymethyl ether with a silyloxyoxirane induced by phosphorus pentoxide.

Pederin: The metallated dihydropyran approach. Stereoselective reduction of N-acylimidates via rhodium-catalysed hydroboration

A synthesis of the insect toxin pederin (1) based upon the union of metallated dihydropyran 8 with the oxamate ester derivative 9 is described. Noteworthy features include (a) a new method for the construction of metallated dihydropyrans which tolerates h

STUDIES RELATED TO THE SYNTHESIS OF (+/-)-PEDERIN. PART 1. SYNTHESIS OF ETHYL PEDERATE AND BENZOYLSELENOPEDERIC ACID.

The first in a series of 2 papers on the synthesis of the insect toxin pederin (1) begins with a discussion of synthesis of the ring A fragments (+/-) pederate (2) and (+/-)-benzoylselenopederic acid (4).A silicon-mediated intramolecular cyclisation of a

The Total Synthesis of (+/-)-Pederin

The conjugate addition of phenylselenomethyl-lithium to the α,β-unsaturated lactone (4) was a key step in a short synthesis of (+/-)-benzoylselenopederic acid (2); union of (2) and (+/-)-benzoylpedamide (3) by a modification of known procedures gave (+/-)-pederin (1).