2-benzyloxymethyl-3-(6-tert-butoxycarbonylamino-5-methylpyridin-3-yl)-2-hydroxymethylpropionic acid tert-butyl ester

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Chemical Name:2-benzyloxymethyl-3-(6-tert-butoxycarbonylamino-5-methylpyridin-3-yl)-2-hydroxymethylpropionic acid tert-butyl ester
CAS No.:685133-74-8
Molecular Formula:C₂₇H₃₈N₂O₆
Molecular Weight:486.609
Hs Code.:

Synonyms:2-benzyloxymethyl-3-(6-tert-butoxycarbonylamino-5-methylpyridin-3-yl)-2-hydroxymethylpropionic acid tert-butyl ester

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Chemical Property of 2-benzyloxymethyl-3-(6-tert-butoxycarbonylamino-5-methylpyridin-3-yl)-2-hydroxymethylpropionic acid tert-butyl ester

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Technology Process of 2-benzyloxymethyl-3-(6-tert-butoxycarbonylamino-5-methylpyridin-3-yl)-2-hydroxymethylpropionic acid tert-butyl ester

There total 8 articles about 2-benzyloxymethyl-3-(6-tert-butoxycarbonylamino-5-methylpyridin-3-yl)-2-hydroxymethylpropionic 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: 72.0%

: 685133-49-7
2-benzyloxymethyl-2-(6-tert-butoxycarbonylamino-5-methylpyridin-3-ylmethyl)malonic acid mono-tert-butyl ester

: 685133-74-8
2-benzyloxymethyl-3-(6-tert-butoxycarbonylamino-5-methylpyridin-3-yl)-2-hydroxymethylpropionic acid tert-butyl ester

Guidance literature:: 2-benzyloxymethyl-2-(6-tert-butoxycarbonylamino-5-methylpyridin-3-ylmethyl)malonic acid mono-tert-butyl ester; With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 5h;

With lithium borohydride; In ethanol; for 0.666667h;
DOI:10.1016/j.bmc.2003.12.039

Reference yield:

: 497159-91-8
2-[N,N-bis(tert-butoxycarbonyl)amino]-5-bromo-3-methylpyridine

: 685133-74-8
2-benzyloxymethyl-3-(6-tert-butoxycarbonylamino-5-methylpyridin-3-yl)-2-hydroxymethylpropionic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 59 percent / (PPh₃)2PdCl₂ / 1,2-dichloro-ethane / 48 h / 90 °C

2.1: 59 percent / Bu₄NF / tetrahydrofuran / 20 °C

3.1: 77 percent / PPh₃; CBr₄ / CH₂Cl₂ / 3 h / 0 - 20 °C

4.1: 59 percent / NaH / tetrahydrofuran / -70 - 20 °C

5.1: 60 percent / LDA / tetrahydrofuran; heptane; ethylbenzene / 0 - 20 °C

6.1: 60 percent / KOH / CH₂Cl₂; ethanol; H₂O / 96 h / 20 °C

7.1: BOP; DIPEA / tetrahydrofuran / 5 h / 20 °C

7.2: 72 percent / LiBH₄ / ethanol / 0.67 h

With potassium hydroxide; carbon tetrabromide; tetrabutyl ammonium fluoride; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; ethanol; n-heptane; dichloromethane; ethylbenzene; water; 1,2-dichloro-ethane;
DOI:10.1016/j.bmc.2003.12.039

Reference yield:

: 3430-21-5
5-bromo-3-methyl-pyridin-2-ylamine

: 685133-74-8
2-benzyloxymethyl-3-(6-tert-butoxycarbonylamino-5-methylpyridin-3-yl)-2-hydroxymethylpropionic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 71 percent / dimethylaminopyridine / 2-methyl-propan-2-ol

2.1: 59 percent / (PPh₃)2PdCl₂ / 1,2-dichloro-ethane / 48 h / 90 °C

3.1: 59 percent / Bu₄NF / tetrahydrofuran / 20 °C

4.1: 77 percent / PPh₃; CBr₄ / CH₂Cl₂ / 3 h / 0 - 20 °C

5.1: 59 percent / NaH / tetrahydrofuran / -70 - 20 °C

6.1: 60 percent / LDA / tetrahydrofuran; heptane; ethylbenzene / 0 - 20 °C

7.1: 60 percent / KOH / CH₂Cl₂; ethanol; H₂O / 96 h / 20 °C

8.1: BOP; DIPEA / tetrahydrofuran / 5 h / 20 °C

8.2: 72 percent / LiBH₄ / ethanol / 0.67 h

With dmap; potassium hydroxide; carbon tetrabromide; tetrabutyl ammonium fluoride; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; ethanol; n-heptane; dichloromethane; ethylbenzene; water; 1,2-dichloro-ethane; tert-butyl alcohol;
DOI:10.1016/j.bmc.2003.12.039