(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(3-cyano-2-nitro-phenoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(3-cyano-2-nitro-phenoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
CAS No.:176718-56-2
Molecular Formula:C₂₀H₂₀N₂O₁₂
Molecular Weight:480.385
Hs Code.:

Synonyms:(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(3-cyano-2-nitro-phenoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

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Chemical Property of (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(3-cyano-2-nitro-phenoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

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Technology Process of (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(3-cyano-2-nitro-phenoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 1 articles about (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(3-cyano-2-nitro-phenoxy)-tetrahydro-pyran-2-carboxylic acid methyl 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: 80.7%

: 129298-23-3
3-hydroxy-2-nitrobenzonitrile

: 21085-72-3
1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

: 176718-56-2
(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(3-cyano-2-nitro-phenoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: With quinoline; silver (II) carbonate; for 15h; Ambient temperature;
DOI:10.1248/cpb.44.547

Reference yield: 73.2%

: 176718-56-2
(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(3-cyano-2-nitro-phenoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

: 176718-57-3
(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(2-amino-3-cyano-phenoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethyl acetate; for 2h; under 760 Torr;
DOI:10.1248/cpb.44.547

Reference yield:

: 176718-56-2
(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(3-cyano-2-nitro-phenoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

: (2S,3S,4S,5R,6S)-6-(2-Amino-5-bromo-3-cyano-phenoxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 73.2 percent / H₂ / 10percent Pd/C / ethyl acetate / 2 h / 760 Torr

2: 90.2 percent / NBS / dimethylformamide / 1 h / Ambient temperature

3: 55.3 percent / 1N aq. NaOH / acetone / 0.25 h / Ambient temperature

With sodium hydroxide; N-Bromosuccinimide; hydrogen; palladium on activated charcoal; In ethyl acetate; N,N-dimethyl-formamide; acetone;
DOI:10.1248/cpb.44.547