66054-36-2

Usage

Core structure

2,4(1H,3H)-Pyrimidinedione

Sugar moiety

2-(acetylamino)-2-deoxy-a-D-glucopyranosyl

Stereochemistry

(11S)-11-O-[...]

Acetylamino group

2-(acetylamino)

Hydrocarbon chain

(2E)-13-methyl-1-oxo-2-tetradecenyl

Amino group attachment

[amino]-L-galacto-b-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl

Derivative of nucleoside

Suggests a building block of DNA and RNA

Potential biological activity

Presence of multiple functional groups

Medicinal or pharmaceutical applications

Suggested by the presence of functional groups and its structure

Upstream product

• 58-96-8 uridine 
• 64317-63-1 ethyl 13-methyltetradecanoate 
• 6946-46-9 9-ethoxycarbonylnonanoic acid chloride 
• 104477-84-1 13-methyl-10-oxo-tetradecanoic acid ethyl ester 
• 117299-89-5 allyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside 
• 107-82-4 i-pentyl bromide 
• 158421-43-3 2',3'-O-bis(allyloxycarbonyl)-5'-O-(dimethoxytrityl)-3-N-(tert-butyloxycarbonyl)uridine 
• 158421-42-2 5'-O-(dimethoxytrityl)-N-(tert-butyloxycarbonyl)uridine 
• 158421-44-4 2',3'-O-bis(allyloxycarbonyl)-3-N-(tert-butyloxycarbonyl)uridine 
• 147158-39-2 C₅₀H₅₈N₄O₁₂SeSi 
• 147158-42-7 C₅₃H₇₆N₄O₂₀Si 
• 158421-37-5 C₄₇H₆₄N₂O₁₃SeSi 
• 1053693-84-7 C₃₇H₆₂N₄O₁₇Si 
• 147158-40-5 {(2S,3R,4R,5R,6S)-2-[(4aR,6R,7R,8R,8aR)-7-Azido-8-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-4-benzyloxymethoxy-5-hydroxy-6-phenylselanylmethyl-tetrahydro-pyran-3-yl}-carbamic acid benzyl ester 

Relevant academic research and scientific papers

Total Synthesis of Tunicamycin v

The total synthesis of tunicamycin V is described. This strategy is based on the initial construction of tunicaminyluracil, which is regarded to play an important role in the observed biological activities. The key to the synthesis was a Mukaiyama aldol reaction followed by a furan-oxidation to construct the undecose skeleton, a [3,3] sigmatropic rearrangement of a cyanate, and a highly selective trehalose-type glycosylation.

Synthetic studies of the tunicamycin antibiotics. Preparation of (+)-tunicaminyluracil, (+)-tunicamycin-V, and 5′-epi-tunicamycin-V

A concise synthetic route to the tunicamycin antibiotics is described, illustrated by the preparation of (+)-tunicamycin-V (1-V). Key features of the synthesis include (1) the development and application of a silicon-mediated reductive coupling of aldehydes and allylic alcohols to construct the undecose core of the natural product and (2) the development of an efficient procedure for the synthesis of the trehalose glycosidic bond within the antibiotic. These innovations allow for the coupling of a uridine-derived aldehyde fragment with a performed trehalose-linked disaccharide allylic alcohol to form the carbohydrate core (1) of the natural product in a highly covergent manner. The resultant amino polyol is a versatile intermediate for the synthesis of any of the homologous tunicamycin antibiotics.

TOTAL SYNTHESIS OF TUNICAMYCIN

The first total synthesis of tunicamycin V, a major component of tunicamycin homologues, is described.Condensation of 2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-propanoyl-α-D-glucopyranose with 1-(11R)-2,3,5,8,9-penta-O-acetyl-10-(benzyloxycarbonyl)ami