(S)-N-benzyloxycarbonyl-O-(4-methoxybenzyl)-3-[4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl]tyrosine tert-butyl ester

Base Information

Chemical Name:(S)-N-benzyloxycarbonyl-O-(4-methoxybenzyl)-3-[4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl]tyrosine tert-butyl ester
CAS No.:935846-53-0
Molecular Formula:C₃₅H₄₄BNO₈
Molecular Weight:617.547
Hs Code.:

Synonyms:(S)-N-benzyloxycarbonyl-O-(4-methoxybenzyl)-3-[4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl]tyrosine tert-butyl ester

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Chemical Property of (S)-N-benzyloxycarbonyl-O-(4-methoxybenzyl)-3-[4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl]tyrosine tert-butyl ester

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Technology Process of (S)-N-benzyloxycarbonyl-O-(4-methoxybenzyl)-3-[4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl]tyrosine tert-butyl ester

There total 3 articles about (S)-N-benzyloxycarbonyl-O-(4-methoxybenzyl)-3-[4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl]tyrosine tert-butyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

: 935846-57-4
(S)-N-benzyloxycarbonyl-O-(4-methoxybenzyl)-3-iodotyrosine tert-butyl ester

: 25015-63-8
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

: 935846-53-0
(S)-N-benzyloxycarbonyl-O-(4-methoxybenzyl)-3-[4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl]tyrosine tert-butyl ester

Guidance literature:: With triethylamine; CyJohnPhos; palladium diacetate; In 1,4-dioxane; at 85 ℃; for 0.5h;
DOI:10.1021/jo062627r

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 935846-53-0
(S)-N-benzyloxycarbonyl-O-(4-methoxybenzyl)-3-[4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl]tyrosine tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / potassium carbonate; 18-crown-6; tetra-n-butylammonium iodide / acetone / 12 h / Heating

2: 70 percent / triethylamine; 2-(dicyclohexylphosphino)biphenyl / palladium(II) acetate / dioxane / 0.5 h / 85 °C

With 18-crown-6 ether; tetra-(n-butyl)ammonium iodide; potassium carbonate; triethylamine; CyJohnPhos; palladium diacetate; In 1,4-dioxane; acetone;
DOI:10.1021/jo062627r

Reference yield:

: 870456-12-5
(S)-N-benzyloxycarbonyl-3-iodotyrosine tert-butyl ester

: 935846-53-0
(S)-N-benzyloxycarbonyl-O-(4-methoxybenzyl)-3-[4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl]tyrosine tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / potassium carbonate; 18-crown-6; tetra-n-butylammonium iodide / acetone / 12 h / Heating

2: 70 percent / triethylamine; 2-(dicyclohexylphosphino)biphenyl / palladium(II) acetate / dioxane / 0.5 h / 85 °C

With 18-crown-6 ether; tetra-(n-butyl)ammonium iodide; potassium carbonate; triethylamine; CyJohnPhos; palladium diacetate; In 1,4-dioxane; acetone;
DOI:10.1021/jo062627r