methyl (2R,3S)-3-[(S)-1-(N-tert-butoxycarbonyl-N-hydroxymethylamino)-2-phenylethyl]-oxirane-2-carboxylate

Base Information

Chemical Name:methyl (2R,3S)-3-[(S)-1-(N-tert-butoxycarbonyl-N-hydroxymethylamino)-2-phenylethyl]-oxirane-2-carboxylate
CAS No.:864165-71-9
Molecular Formula:C₁₈H₂₅NO₆
Molecular Weight:351.4
Hs Code.:

Synonyms:methyl (2R,3S)-3-[(S)-1-(N-tert-butoxycarbonyl-N-hydroxymethylamino)-2-phenylethyl]-oxirane-2-carboxylate

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Chemical Property of methyl (2R,3S)-3-[(S)-1-(N-tert-butoxycarbonyl-N-hydroxymethylamino)-2-phenylethyl]-oxirane-2-carboxylate

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Technology Process of methyl (2R,3S)-3-[(S)-1-(N-tert-butoxycarbonyl-N-hydroxymethylamino)-2-phenylethyl]-oxirane-2-carboxylate

There total 3 articles about methyl (2R,3S)-3-[(S)-1-(N-tert-butoxycarbonyl-N-hydroxymethylamino)-2-phenylethyl]-oxirane-2-carboxylate 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: 77.0%

: C₁₉H₂₅NO₇

: 864165-71-9
methyl (2R,3S)-3-[(S)-1-(N-tert-butoxycarbonyl-N-hydroxymethylamino)-2-phenylethyl]-oxirane-2-carboxylate

Guidance literature:: C₁₉H₂₅NO₇; With dihydrogen peroxide; magnesium sulfate; toluene-4-sulfonic acid; In 1,2-dimethoxyethane; water; at 20 ℃; for 4h;

With potassium carbonate; In methanol; 1,2-dimethoxyethane; water; at 20 ℃; for 0.5h; optical yield given as %de; diastereoselective reaction;
DOI:10.1016/j.tetasy.2011.09.021

Reference yield:

: methyl (2E,4S)-4-(N-tert-butoxycarbonyl-N-hydroxymethyl)amino-5-phenylpent-2-enoate

: 864165-71-9
methyl (2R,3S)-3-[(S)-1-(N-tert-butoxycarbonyl-N-hydroxymethylamino)-2-phenylethyl]-oxirane-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: dmap; triethylamine / dichloromethane / 1 h / 20 °C

2.1: dihydrogen peroxide; magnesium sulfate; toluene-4-sulfonic acid / 1,2-dimethoxyethane; water / 4 h / 20 °C

2.2: 0.5 h / 20 °C

With dmap; dihydrogen peroxide; magnesium sulfate; toluene-4-sulfonic acid; triethylamine; In 1,2-dimethoxyethane; dichloromethane; water;
DOI:10.1016/j.tetasy.2011.09.021

Reference yield:

: (4S)-4-benzyl-3-(tert-butoxycarbonyl)-5-hydroxyoxazolidine

: 864165-71-9
methyl (2R,3S)-3-[(S)-1-(N-tert-butoxycarbonyl-N-hydroxymethylamino)-2-phenylethyl]-oxirane-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: benzene / 2 h / Reflux

2.1: dmap; triethylamine / dichloromethane / 1 h / 20 °C

3.1: dihydrogen peroxide; magnesium sulfate; toluene-4-sulfonic acid / 1,2-dimethoxyethane; water / 4 h / 20 °C

3.2: 0.5 h / 20 °C

With dmap; dihydrogen peroxide; magnesium sulfate; toluene-4-sulfonic acid; triethylamine; In 1,2-dimethoxyethane; dichloromethane; water; benzene;
DOI:10.1016/j.tetasy.2011.09.021