[((2S,3S,4R,5R,6R)-5-Amino-3,4-dihydroxy-6-phenethyloxy-tetrahydro-pyran-2-carbonyl)-amino]-acetic acid methyl ester

Base Information

Chemical Name:[((2S,3S,4R,5R,6R)-5-Amino-3,4-dihydroxy-6-phenethyloxy-tetrahydro-pyran-2-carbonyl)-amino]-acetic acid methyl ester
CAS No.:870529-38-7
Molecular Formula:C₁₇H₂₄N₂O₇
Molecular Weight:368.387
Hs Code.:

Synonyms:[((2S,3S,4R,5R,6R)-5-Amino-3,4-dihydroxy-6-phenethyloxy-tetrahydro-pyran-2-carbonyl)-amino]-acetic acid methyl ester

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Chemical Property of [((2S,3S,4R,5R,6R)-5-Amino-3,4-dihydroxy-6-phenethyloxy-tetrahydro-pyran-2-carbonyl)-amino]-acetic acid methyl ester

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Technology Process of [((2S,3S,4R,5R,6R)-5-Amino-3,4-dihydroxy-6-phenethyloxy-tetrahydro-pyran-2-carbonyl)-amino]-acetic acid methyl ester

There total 8 articles about [((2S,3S,4R,5R,6R)-5-Amino-3,4-dihydroxy-6-phenethyloxy-tetrahydro-pyran-2-carbonyl)-amino]-acetic 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:

: 870529-17-2
2-phenylethyl 2-{[(benzyloxy)carbonyl]amino}-2-deoxy-N-{[(methoxy)carbonyl]methyl}-β-D-glucopyranosiduronamide

: 870529-38-7
[((2S,3S,4R,5R,6R)-5-Amino-3,4-dihydroxy-6-phenethyloxy-tetrahydro-pyran-2-carbonyl)-amino]-acetic acid methyl ester

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethanol; under 760 Torr;
DOI:10.1002/hlca.200590175

Reference yield:

: 35946-66-8
2-(acetoxymethyl)-5-{[(benzyloxy)carbonyl]amino}tetrahydropyran-3,4,6-triyl triacetate

: 870529-38-7
[((2S,3S,4R,5R,6R)-5-Amino-3,4-dihydroxy-6-phenethyloxy-tetrahydro-pyran-2-carbonyl)-amino]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: Drierite; 3A MS / CH₂Cl₂ / 0.5 h / 20 °C

1.2: 43 percent / TMSOTf / CH₂Cl₂ / 0.25 h

2.1: Na / methanol / 20 °C

2.2: 60 percent / TEMPO; NaClO₂; NaHCO₃ / Borax / acetonitrile; H₂O / 0.5 h / pH 9.0

3.1: 82 percent / HOBt; EDC hydrochloride; Et(iPr)2N / CH₂Cl₂ / 20 °C

4.1: H₂ / Pd/C / ethanol / 760 Torr

With calcium sulfate; hydrogen; sodium; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; ethanol; dichloromethane;
DOI:10.1002/hlca.200590175

Reference yield:

: 114297-26-6
1,3,4,6-tetra-O-acetyl-2-deoxy-2-{[(4-methoxyphenyl)methylidene]amino}-D-glucopyranose

: 870529-38-7
[((2S,3S,4R,5R,6R)-5-Amino-3,4-dihydroxy-6-phenethyloxy-tetrahydro-pyran-2-carbonyl)-amino]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 100 percent / HCl / acetone

2.1: 83 percent / NaHCO₃ / CHCl₃; H₂O / pH 8.0

3.1: Drierite; 3A MS / CH₂Cl₂ / 0.5 h / 20 °C

3.2: 43 percent / TMSOTf / CH₂Cl₂ / 0.25 h

4.1: Na / methanol / 20 °C

4.2: 60 percent / TEMPO; NaClO₂; NaHCO₃ / Borax / acetonitrile; H₂O / 0.5 h / pH 9.0

5.1: 82 percent / HOBt; EDC hydrochloride; Et(iPr)2N / CH₂Cl₂ / 20 °C

6.1: H₂ / Pd/C / ethanol / 760 Torr

With hydrogenchloride; calcium sulfate; hydrogen; sodium; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; ethanol; dichloromethane; chloroform; water; acetone;
DOI:10.1002/hlca.200590175