(S)-3-(2,6-bis((benzyloxy)methoxy)-4-((E)-prop-1-en-1-yl)phenyl)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2-dimethylpropanamide

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Chemical Name:(S)-3-(2,6-bis((benzyloxy)methoxy)-4-((E)-prop-1-en-1-yl)phenyl)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2-dimethylpropanamide
CAS No.:1450741-58-8
Molecular Formula:C₃₉H₄₅NO₆
Molecular Weight:623.789
Hs Code.:

Synonyms:(S)-3-(2,6-bis((benzyloxy)methoxy)-4-((E)-prop-1-en-1-yl)phenyl)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2-dimethylpropanamide

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Chemical Property of (S)-3-(2,6-bis((benzyloxy)methoxy)-4-((E)-prop-1-en-1-yl)phenyl)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2-dimethylpropanamide

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Technology Process of (S)-3-(2,6-bis((benzyloxy)methoxy)-4-((E)-prop-1-en-1-yl)phenyl)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2-dimethylpropanamide

There total 10 articles about (S)-3-(2,6-bis((benzyloxy)methoxy)-4-((E)-prop-1-en-1-yl)phenyl)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2-dimethylpropanamide 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: 55.0%

: 1450741-55-5
3,5-bis((benzyloxy)methoxy)-4-bromo-1-(E)-prop-1-en-1-ylbenzene

: potassium (S)-3-(trifluoroborato)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2-dimethylpropanamide

: 1450741-58-8
(S)-3-(2,6-bis((benzyloxy)methoxy)-4-((E)-prop-1-en-1-yl)phenyl)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2-dimethylpropanamide

Guidance literature:: With palladium diacetate; potassium carbonate; ruphos; In water; toluene; at 85 ℃; for 1.5h; enantioselective reaction; Inert atmosphere;
DOI:10.1021/jo5008527

Reference yield:

: 3,5-bis((benzyloxy)methoxy)-4-bromo-1-prop-1-en-1-ylbenzene

: 1450741-58-8
(S)-3-(2,6-bis((benzyloxy)methoxy)-4-((E)-prop-1-en-1-yl)phenyl)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2-dimethylpropanamide

Guidance literature:: Multi-step reaction with 2 steps

1: (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II) / toluene / 16 h / Inert atmosphere; Schlenk technique; Reflux

2: palladium diacetate; ruphos; potassium carbonate / toluene; water / 1.5 h / 85 °C / Inert atmosphere; Schlenk technique

With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); palladium diacetate; potassium carbonate; ruphos; In water; toluene; 2: |Suzuki Coupling;
DOI:10.1021/ol402191t

Reference yield:

: 1450741-52-2
(benzyloxy)methyl 3,5-bis((benzyloxy)methoxy)-4-bromobenzoate

: 1450741-58-8
(S)-3-(2,6-bis((benzyloxy)methoxy)-4-((E)-prop-1-en-1-yl)phenyl)-N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N,2-dimethylpropanamide

Guidance literature:: Multi-step reaction with 4 steps

1: diisobutylaluminium hydride / dichloromethane; cyclohexane / 0.25 h / -78 - 0 °C / Inert atmosphere; Schlenk technique

2: N-ethyl-N,N-diisopropylamine; sulfur trioxide pyridine complex; dimethyl sulfoxide / dichloromethane / 0.25 h / 0 °C / Inert atmosphere; Schlenk technique

3: 18-crown-6 ether; potassium tert-butylate / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere; Schlenk technique

4: palladium diacetate; ruphos; potassium carbonate / toluene; water / 1.5 h / 85 °C / Inert atmosphere; Schlenk technique

With 18-crown-6 ether; potassium tert-butylate; palladium diacetate; sulfur trioxide pyridine complex; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; ruphos; In dichloromethane; cyclohexane; water; toluene; 3: |Wittig Olefination / 4: |Suzuki Coupling;
DOI:10.1021/ol402191t