(1S,2S,3E)-1-[(1S)-1-p-methoxybenzyloxymethoxyethyl]-2-hydroxy-5-(benzyloxypent-3-enyloxy)acetic acid tert-butyl ester

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Chemical Name:(1S,2S,3E)-1-[(1S)-1-p-methoxybenzyloxymethoxyethyl]-2-hydroxy-5-(benzyloxypent-3-enyloxy)acetic acid tert-butyl ester
CAS No.:264132-39-0
Molecular Formula:C₂₉H₄₀O₈
Molecular Weight:516.632
Hs Code.:

Synonyms:(1S,2S,3E)-1-[(1S)-1-p-methoxybenzyloxymethoxyethyl]-2-hydroxy-5-(benzyloxypent-3-enyloxy)acetic acid tert-butyl ester

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Chemical Property of (1S,2S,3E)-1-[(1S)-1-p-methoxybenzyloxymethoxyethyl]-2-hydroxy-5-(benzyloxypent-3-enyloxy)acetic acid tert-butyl ester

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Technology Process of (1S,2S,3E)-1-[(1S)-1-p-methoxybenzyloxymethoxyethyl]-2-hydroxy-5-(benzyloxypent-3-enyloxy)acetic acid tert-butyl ester

There total 4 articles about (1S,2S,3E)-1-[(1S)-1-p-methoxybenzyloxymethoxyethyl]-2-hydroxy-5-(benzyloxypent-3-enyloxy)acetic acid 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: 65.0%

: 84666-31-9,109669-46-7,243662-95-5
<(1E)-3-(benzyloxy)-1-propen-1-yl>tributylstannate

: 264132-38-9
(1R,2S)-[2-(p-methoxybenzyloxymethoxy)-1-ethenylpropoxy]acetic acid tert-butyl ester

: 264132-39-0
(1S,2S,3E)-1-[(1S)-1-p-methoxybenzyloxymethoxyethyl]-2-hydroxy-5-(benzyloxypent-3-enyloxy)acetic acid tert-butyl ester

Guidance literature:: (1R,2S)-[2-(p-methoxybenzyloxymethoxy)-1-ethenylpropoxy]acetic acid tert-butyl ester; With ozone; triphenylphosphine; In dichloromethane; at -78 ℃;

<(1E)-3-(benzyloxy)-1-propen-1-yl>tributylstannate; With copper(l) iodide; n-butyllithium; tributylphosphine; In tetrahydrofuran; diethyl ether; hexane; at -78 ℃; for 2h; Further stages.;
DOI:10.1021/jo991681n

Reference yield:

: 88023-78-3
para-methoxybenzyl chloride

: 264132-39-0
(1S,2S,3E)-1-[(1S)-1-p-methoxybenzyloxymethoxyethyl]-2-hydroxy-5-(benzyloxypent-3-enyloxy)acetic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 96 percent / diisopropylethylamine / CH₂Cl₂ / 0 - 20 °C

2.1: lithium borohydride / tetrahydrofuran / -78 °C

2.2: tetrahydrofuran / -30 - 0 °C

2.3: 7.848 g / NaOH; tetrabutylammonium hydrogen sulfate / benzene / 2.5 h / 0 °C

3.1: ozone; Ph₃P / CH₂Cl₂ / -78 °C

3.2: 65 percent / CuI; n-Bu₃P; BuLi / diethyl ether; tetrahydrofuran; hexane / 2 h / -78 °C

With lithium borohydride; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; 1.1: Substitution / 2.1: Reduction / 2.2: Addition / 2.3: Alkylation / 3.1: Oxidation / 3.2: Addition;
DOI:10.1021/jo991681n

Reference yield:

: p-methoxybenzyloxymethyl methyl sulfide

: 264132-39-0
(1S,2S,3E)-1-[(1S)-1-p-methoxybenzyloxymethoxyethyl]-2-hydroxy-5-(benzyloxypent-3-enyloxy)acetic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: sulfuryl chloride / CH₂Cl₂ / 1.5 h / -78 °C

2.1: 96 percent / diisopropylethylamine / CH₂Cl₂ / 0 - 20 °C

3.1: lithium borohydride / tetrahydrofuran / -78 °C

3.2: tetrahydrofuran / -30 - 0 °C

3.3: 7.848 g / NaOH; tetrabutylammonium hydrogen sulfate / benzene / 2.5 h / 0 °C

4.1: ozone; Ph₃P / CH₂Cl₂ / -78 °C

4.2: 65 percent / CuI; n-Bu₃P; BuLi / diethyl ether; tetrahydrofuran; hexane / 2 h / -78 °C

With lithium borohydride; sulfuryl dichloride; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; 1.1: Substitution / 2.1: Substitution / 3.1: Reduction / 3.2: Addition / 3.3: Alkylation / 4.1: Oxidation / 4.2: Addition;
DOI:10.1021/jo991681n