352670-32-7

Upstream product

• 149-73-5 trimethyl orthoformate 
• 100-39-0 benzyl bromide 
• 1421851-07-1 (1R)-1-((1R,2S,3S,6S)-2-(benzyloxy)-4-(dimethoxymethyl)-6-methyl-3-(2,2,2-trichloroacetamido)-7-oxabicyclo[4.1.0]heptan-3-yl)prop-2-yn-1-yl acetate 
• 1421851-18-4 C₂₅H₃₄Cl₃NO₆Si 
• 1421851-06-0 N-((1R,2S,3R,6S)-2-(benzyloxy)-4-(dimethoxymethyl)-3-formyl-6-methyl-7-oxabicyclo[4.1.0]heptan-3-yl)-2,2,2-trichloroacetamide 
• 1421851-05-9 N-((1R,2S,3R,6S)-2-(benzyloxy)-4-(dimethoxymethyl)-6-methyl-3-vinyl-7-oxabicyclo[4.1.0]heptan-3-yl)-2,2,2-trichloroacetamide 
• 1421851-04-8 2,2,2-trichloro-N-((1R,2S,3R,6S)-4-(dimethoxymethyl)-2-hydroxy-6-methyl-3-vinyl-7-oxabicyclo[4.1.0]heptan-3-yl)acetamide 
• 1421851-03-7 2,2,2-trichloro-N-((1R,2R)-6-(dimethoxymethyl)-2-hydroxy-4-methyl-1-vinylcyclohex-3-en-1-yl)acetamide 
• 1421851-02-6 2,2,2-trichloro-N-((1R)-6-(dimethoxymethyl)-4-methyl-2-oxo-1-vinylcyclohex-3-en-1-yl)acetamide 
• 253674-37-2 Acetic acid (1S,4S,5R,6S,8S,9S)-9-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-8-hydroxy-8-methyl-3-oxo-5-(2,2,2-trichloro-acetylamino)-2-oxa-bicyclo[3.3.1]non-4-yl ester 
• 253674-46-3 Acetic acid (R)-1-[(1R,2S,3S,4S,6S)-2-benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-3-(2,2,2-trichloro-acetylamino)-7-oxa-bicyclo[4.1.0]hept-3-yl]-prop-2-ynyl ester 
• 253674-43-0 N-[(1R,2S,3R,4S,6S)-2-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-3-vinyl-7-oxa-bicyclo[4.1.0]hept-3-yl]-2,2,2-trichloro-acetamide 
• 253674-44-1 N-[(1R,2S,3R,4S,6S)-2-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-formyl-6-methyl-7-oxa-bicyclo[4.1.0]hept-3-yl]-2,2,2-trichloro-acetamide 
• 253674-40-7 2,2,2-Trichloro-N-[(1R,2S,4S,5S)-4,5-dibromo-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-1-vinyl-cyclohexyl]-acetamide 

Downstream Products

• 253674-50-9 Acetic acid (1S,4S,6R,7S,8R,9S,10S)-9-benzyloxy-8-(3-benzyl-ureido)-6-methoxy-10-methyl-3-oxo-2,5-dioxa-tricyclo[5.2.2.0^4,8]undec-10-yl ester 
• 352670-33-8 Acetic acid (1S,4S,5R,6S,8S,9S)-8-acetoxy-9-benzyloxy-5-(3-benzyl-ureido)-6-dimethoxymethyl-8-methyl-3-oxo-2-oxa-bicyclo[3.3.1]non-4-yl ester 
• 253674-52-1 Acetic acid (1S,4S,6R,7S,8R,9S,10S)-8-(N'-acetyl-N',N''-dibenzyl-guanidino)-9-benzyloxy-6-methoxy-10-methyl-3-oxo-2,5-dioxa-tricyclo[5.2.2.0^4,8]undec-10-yl ester 
• 1421851-09-3 C₂₀H₂₂Cl₃NO₇ 
• 1421851-10-6 C₂₀H₂₂Cl₃NO₇ 
• 1421851-11-7 C₂₉H₄₁N₃O₁₀ 
• 1421851-14-0 C₂₉H₄₁N⁽¹⁵⁾N₂O₁₀ 
• 253674-49-6 Acetic acid (1S,4S,5R,6S,8S,9S)-8-acetoxy-9-benzyloxy-6-dimethoxymethyl-8-methyl-3-oxo-5-(2,2,2-trichloro-acetylamino)-2-oxa-bicyclo[3.3.1]non-4-yl ester 

Relevant academic research and scientific papers

An improved synthesis of (-)-5,11-dideoxytetrodotoxin

We describe an improved synthesis of (-)-5,11-dideoxytetrodotoxin from an enone, which was used for synthesis of tetrodotoxin and its analogues in this laboratory. One of the major modifications was to establish a two-step guanidinylation of trichloroacetamide of a highly functionalized intermediate, which allowed us to prepare 15N2-labeled 5,11-dideoxytetrodotoxin for biosynthetic investigations.

Stereocontrolled synthesis of (-)-5,11-dideoxytetrodotoxin

Asymmetric synthesis of (-)-5,11-dideoxytetrodotoxin, an analog of puffer fish toxin, was accomplished from a common key intermediate through a novel hydroxylation at the C-8 position with neighboring group participation of trichloroacetamide, a highly st

Stereocontrolled synthesis of (-)-5,11-dideoxytetrodotoxin

New derivatives of an intriguing marine natural product are now accessible. The first asymmetric synthesis of the simple tetrodotoxin analogue, 5,11-dideoxytetrodotoxin (3), was achieved. Hydroxylation at position C8 of the key intermediate 1 relied on th