717916-68-2

Upstream product

• 35052-27-8 3,5-dimethoxy-4-methylphenylmethyl alcohol 
• 114972-96-2 2,6-dimethoxy-4-methoxymethyltoluene 
• 717916-70-6 C₃₇H₇₂O₇Si₂ 
• 717916-77-3 Acetic acid (1R,2S,3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-1-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-5-(3,5-dimethoxy-4-methyl-phenyl)-2,4-dimethyl-pentyl ester 
• 717916-67-1 (2S,3R,4S,5R,8S)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-1-(3,5-dimethoxy-4-methyl-phenyl)-2,4,8-trimethyl-nonan-5-ol 
• 717916-65-9 (2S,3R,4S)-1-(3,5-Dimethoxy-4-methyl-phenyl)-2,4-dimethyl-hex-5-en-3-ol 
• 717916-64-8 (S)-3-(3,5-Dimethoxy-4-methyl-phenyl)-2-methyl-propan-1-ol 
• 717916-63-7 5-iodomethyl-1,3-dimethoxy-2-methyl-benzene 

Downstream Products

• 717916-62-6 (2-{(2R,3S,4S,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-3,5-dimethyl-tetrahydro-pyran-2-yl}-3,4,6-trimethoxy-5-methyl-phenyl)-acetaldehyde 
• 717916-75-1 (2R,3S,4S,5S,6R)-2-(2-Allyl-3,5,6-trimethoxy-4-methyl-phenyl)-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-3,5-dimethyl-tetrahydro-pyran 
• 717916-74-0 2-Allyl-3-{(2R,3S,4S,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-6-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-3,5-dimethyl-tetrahydro-pyran-2-yl}-5-methoxy-6-methyl-benzene-1,4-diol 
• 1620643-72-2 C₂₉H₅₂O₇Si 
• 1620643-74-4 C₃₀H₅₀Br₂O₆Si 
• 1620643-42-6 C₃₁H₅₂O₆Si 
• 1620643-71-1 C₃₅H₆₆O₇Si₂ 
• 1620643-73-3 C₂₉H₅₀O₇Si 
• 717916-71-7 6-{(2R,3S,4S,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-3,5-dimethyl-tetrahydro-pyran-2-yl}-2,4-dimethoxy-3-methyl-phenol 

Relevant academic research and scientific papers

Total synthesis of the antibiotic kendomycin: A macrocyclization using the Tsuji-Trost etherification

A highly stereocontrolled, convergent total synthesis of kendomycin [(-)-TAN2162], an ansa-macrocyclic antibiotic, is reported. The key of the strategy is an unprecedented Tsuji-Trost macrocyclic etherification, followed by a transannular Claisen rearrangement to construct the 18-membered carbocyclic framework. The oxa-six- and five-membered rings were also stereoselectively constructed respectively by a cascade oxidative cyclization at an unfunctionalized benzylic position and using a one-pot epoxidation/5-exo-tet epoxide opening. A new construct: The asymmetric total synthesis of the antibiotic kendomycin was accomplished by using a highly stereocontrolled convergent route. The key feature of the synthetic strategy is the construction of an 18-membered carbocycle based on an intramolecular Tsuji-Trost etherification/transannular Claisen rearrangement sequence. TBS=tert- butyldimethylsilyl.

Synthetic approach to kendomycin: Preparation of the C-glycosidic core

Synthesis of the C13-C19 C-glycoside portion of kendomycin was achieved via oxidative pyran cyclization and Claisen rearrangement to construct the fully functionalized aromatic ring.