N-((2S,3R,4R,5R)-4,5-dihydroxy-2,4-dimethyl-6-oxo(3,4,5-trihydro-2H-pyran-3-yl))(phenylmethoxy)carboxamide

Base Information

Chemical Name:N-((2S,3R,4R,5R)-4,5-dihydroxy-2,4-dimethyl-6-oxo(3,4,5-trihydro-2H-pyran-3-yl))(phenylmethoxy)carboxamide
CAS No.:374073-20-8
Molecular Formula:C₁₅H₁₉NO₆
Molecular Weight:309.319
Hs Code.:

Synonyms:N-((2S,3R,4R,5R)-4,5-dihydroxy-2,4-dimethyl-6-oxo(3,4,5-trihydro-2H-pyran-3-yl))(phenylmethoxy)carboxamide

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Chemical Property of N-((2S,3R,4R,5R)-4,5-dihydroxy-2,4-dimethyl-6-oxo(3,4,5-trihydro-2H-pyran-3-yl))(phenylmethoxy)carboxamide

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Technology Process of N-((2S,3R,4R,5R)-4,5-dihydroxy-2,4-dimethyl-6-oxo(3,4,5-trihydro-2H-pyran-3-yl))(phenylmethoxy)carboxamide

There total 8 articles about N-((2S,3R,4R,5R)-4,5-dihydroxy-2,4-dimethyl-6-oxo(3,4,5-trihydro-2H-pyran-3-yl))(phenylmethoxy)carboxamide 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: 71.0%

: 374073-08-2
(4R,5S)-4-[(R)-1-Hydroxy-1-((R)-3-oxo-1,4-dioxa-spiro[4.5]dec-2-yl)-ethyl]-2,2,5-trimethyl-oxazolidine-3-carboxylic acid benzyl ester

: 374073-20-8
N-((2S,3R,4R,5R)-4,5-dihydroxy-2,4-dimethyl-6-oxo(3,4,5-trihydro-2H-pyran-3-yl))(phenylmethoxy)carboxamide

Guidance literature:: With acetic acid; In water; at 70 ℃; for 16h;
DOI:10.1021/ol016416e

Reference yield: 71.0%

: phenylmethyl 4-[1-(1,4-dioxa-3-oxospiro[4.5]dec-2-yl)-1-hydroxyethyl]-(4R,5S)-2,2,5-trimethyl-1,3-oxazolidine-3-carboxylate

: 374073-20-8
N-((2S,3R,4R,5R)-4,5-dihydroxy-2,4-dimethyl-6-oxo(3,4,5-trihydro-2H-pyran-3-yl))(phenylmethoxy)carboxamide

Guidance literature:: With acetic acid; at 70 ℃; for 16h;
DOI:10.1016/j.tet.2008.02.001

Reference yield:

: 84449-06-9
methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate

: 374073-20-8
N-((2S,3R,4R,5R)-4,5-dihydroxy-2,4-dimethyl-6-oxo(3,4,5-trihydro-2H-pyran-3-yl))(phenylmethoxy)carboxamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: 11.96 g / toluenesulfonic acid monohydrate / benzene / 12 h / 20 °C

2.1: isopropylmagnesium chloride / tetrahydrofuran / 0.08 h / -78 °C

2.2: 93 percent / tetrahydrofuran / -78 - -40 °C

3.1: 69 percent / tetrahydrofuran; diethyl ether / -40 - 20 °C

4.1: diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 0.25 h / -50 °C

4.2: 80 percent / tetrahydrofuran; hexane / 2 h / -78 °C

5.1: 71 percent / glacial acetic acid / H₂O / 16 h / 70 °C

With n-butyllithium; isopropylmagnesium chloride; toluene-4-sulfonic acid; acetic acid; diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; water; benzene;
DOI:10.1021/ol016416e