103728-85-4

Upstream product

• 94493-08-0 C₁₂H₂₁ClO₅ 
• 94536-95-5 (+/-)-3,4-dimethoxybutanal 
• 94493-07-9 4-Hydroxy-6,7-dimethoxy-3,3-dimethyl-heptan-2-one 
• 65335-67-3 (1,2-Dimethyl-propenyloxy)-dimethyl-phenyl-silane 
• 7677-24-9 trimethylsilyl cyanide 
• 103577-07-7 Benzoic acid (2R,4R)-6-acetoxy-2-((S)-2,3-dimethoxy-propyl)-3,3-dimethyl-tetrahydro-pyran-4-yl ester 
• 105878-76-0 [(2S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-4-(2-ethoxy-ethoxy)-2-hydroxy-3,3-dimethyl-tetrahydro-pyran-2-yl]-acetic acid tert-butyl ester 
• 105878-75-9 (S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-4-(2-ethoxy-ethoxy)-3,3-dimethyl-tetrahydro-pyran-2-one 
• 103576-98-3 (S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-3,3-dimethyl-tetrahydro-pyran-2-one 
• 103577-06-6 Benzoic acid (2R,4R,6S)-2-((S)-2,3-dimethoxy-propyl)-6-methoxymethoxy-3,3-dimethyl-tetrahydro-pyran-4-yl ester 
• 103577-04-4 (R)-9-((S)-2,3-Dimethoxy-propyl)-10,10-dimethyl-8-oxa-1,4-dithia-spiro[4.5]decan-7-one 
• 105878-78-2 (2R,6S)-2-((S)-2,3-Dimethoxy-propyl)-6-methoxymethoxy-3,3-dimethyl-tetrahydro-pyran-4-one 
• 103577-03-3 (R)-9-((S)-2,3-Dihydroxy-propyl)-10,10-dimethyl-8-oxa-1,4-dithia-spiro[4.5]decan-7-one 
• 103577-05-5 (7R,9S)-7-((S)-2,3-Dimethoxy-propyl)-9-methoxymethoxy-6,6-dimethyl-8-oxa-1,4-dithia-spiro[4.5]decane 

Downstream Products

• 73787-23-2 (+/-)-18-epi-benzoylpedamide 
• 73787-25-4 Benzoic acid (2R,4R,6S)-2-((S)-2,3-dimethoxy-propyl)-6-methoxycarbonimidoyl-3,3-dimethyl-tetrahydro-pyran-4-yl ester 
• 104432-05-5 C₄₅H₅₇NO₁₁Se 
• 73787-23-2 (+)-benzoylpedamide 
• 103728-87-6 Benzoic acid (2R,4R,6R)-6-carbamoyl-2-((S)-2,3-dimethoxy-propyl)-3,3-dimethyl-tetrahydro-pyran-4-yl ester 

Relevant academic research and scientific papers

Allylboration-reactions, the key to a short synthesis of benzoyl-pedamide

Benzoyl-pedamide (2) a key building block for the synthesis of pederin, has been synthesized in 13 steps from malic acid. The new stereogenic centers have been generated under reagent control of diastereoselectivity with selectivities of 87 and 80% using the newly developed chiral α-substituted allylboronate 16 as well as 21 as reagents.

Studies related to the synthesis of pederin. Part 2. Synthesis of pederol dibenzoate and benzoylpedamide

Syntheses of the ring B fragments (+)-pederol dibenzoate (2) and (±)-benzoylpedamide (3) of the insect toxin pederin (1) are described. An intramolecular directed aldol condensation was used to construct the tetrahydropyran ring in (+)-pederol dibenzoate

TOTAL SYNTHESIS OF (+)-PEDERIN. 1. STEREOCONTROLLED SYNTHESIS OF (+)-BENZOYLPEDAMIDE

(+)-Benzoylpedamide (5), a right half of (+)-pederin (1), was synthesized stereoselectively based on the newly developed method for the synthesis of 1,3-syn- and 1,3-anti-polyols.

Synthetic Approaches to Pederin. A Synthesis of (+/-)-Benzoylpedamide

A Lewis acid-catalysed addition of Me3SiCN to a 4-oxo-3,4-dihydro-2H-pyran is a key step in the synthesis of (+/-)-benzoylpedamide (2).