146346-85-2

Upstream product

• 1164-16-5 Z-L-Tyr-OH 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 60-18-4 L-tyrosine 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 1401229-73-9 C₂₉H₄₅NO₄Si 
• 1401229-64-8 C₁₇H₂₅NO₃Si 
• 862368-92-1 3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-3-hydroxy-2-(2-nitro-benzenesulfonylamino)-propionic acid tert-butyl ester 
• 862368-93-2 3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-3-fluoro-2-(2-nitro-benzenesulfonylamino)-propionic acid tert-butyl ester 
• 862368-91-0 3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-(2-nitro-benzenesulfonylamino)-propionic acid tert-butyl ester 
• 960316-86-3 (Z)-3-(4-Hydroxy-phenyl)-2-((3S,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-3,4,5,6-tetrahydro-pyridin-2-ylamino)-acrylic acid tert-butyl ester 
• 862368-97-6 (Z)-3-(4-Hydroxy-phenyl)-2-((3S,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-3,4,5,6-tetrahydro-pyridin-2-ylamino)-acrylic acid 
• 862368-90-9 2-amino-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid tert-butyl ester 
• 862368-94-3 2-amino-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-3-fluoro-propionic acid tert-butyl ester 
• 862368-89-6 2-benzyloxycarbonylamino-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid tert-butyl ester 

Relevant academic research and scientific papers

Synthesis of N -acyl- N, O -acetals mediated by titanium ethoxide

N-Acyl-N,O-acetals are present in a number of bioactive natural products, and this unusual functional group can act as a synthetic precursor to unstable reactive N-acylimines. In this paper, a variety of N-acyl-O-ethyl-N,O-acetals was concisely prepared under mild conditions mediated by titanium ethoxide (Ti(OEt)4). The method also offers a new strategy to make other O-alkyl-N,O-acetals. Furthermore, this strategy was extended to the synthesis of an analogue of the natural product turtschamide.

First total synthesis of epicoccarine A via O- to C-acyl rearrangement strategy

The first total synthesis of antibacterial epicoccarine A isolated from a fungus Epicoccum sp. has been accomplished in 10 steps along with synthetic elaboration of its C5-epimer, highlighting the utility of O- to C-acyl rearrangement of a 4-O-acyltetramic acid derivative. Comparison of spectroscopic properties and specific optical rotations of the synthetic samples with those reported for authentic material has clearly indicated the unspecified absolute stereochemistry of this natural product to be 5S.

Concise synthesis of glyconoamidines as affinity ligands for the purification of β-glucosidase involved in control of some biological events including plant leaf movement

Glycosidases are involved in deactivation or storage of some endogenous bioactive substances through biologically intriguing processes. For example, nyctinastic leaf movement is controlled by a biological clock through the regulation of β-glucosidase activity. Ganem's glyconoamidine (1) is used as a micromolar inhibitor of glucosidase in biochemical studies and would be useful as an affinity ligand for purification of glycosidase. However, its use for the specific inhibition of glucosidase which is highly specific to a glycoside with voluntary aglycon is seriously restricted because no universal method for the synthesis of N-alkylated glyconoamidine has been reported. Here, we report a concise synthesis of N-alkylated Ganem's glyconoamidine with voluntary aglycon using a non-protected sugar derivative.

Application of t-Butyldimethylsilyl Ethers of Serine, Threonine and Tyrosine in Peptide Synthesis

The utility of Tbdms (t-butyldimethylsilyl) ethers, prepared conveniently in a one pot procedure from Nα-Fmoc (9-fluorenylmethoxycarbonyl) and Nα-Z (benzyloxycarbonyl) hydroxyamino acids, is demonstrated: peptide bond formation and esterification to 4-alkoxybenzylalcohol resin are achieved readily with these derivatives.The lability of the Tbdms ethers to various reagents enables selective deprotection of the hydroxyl side-chains assembly, desirable, e.g., for phosphorylation of glycosylation.