(S)-N-((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-2-benzyloxycarbonylamino-succinamic acid isobutyl ester

Base Information

Chemical Name:(S)-N-((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-2-benzyloxycarbonylamino-succinamic acid isobutyl ester
CAS No.:408363-43-9
Molecular Formula:C₂₄H₃₅N₃O₁₀
Molecular Weight:525.556
Hs Code.:

(S)-N-((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-2-benzyloxycarbonylamino-succinamic acid isobutyl ester

Synonyms:(S)-N-((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-2-benzyloxycarbonylamino-succinamic acid isobutyl ester

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Chemical Property of (S)-N-((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-2-benzyloxycarbonylamino-succinamic acid isobutyl ester

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Technology Process of (S)-N-((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-2-benzyloxycarbonylamino-succinamic acid isobutyl ester

There total 4 articles about (S)-N-((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-2-benzyloxycarbonylamino-succinamic acid isobutyl 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: 84.0%

: 4229-38-3,102039-79-2,115350-20-4,133677-75-5,137493-97-1
2-acetamido-2-deoxy-β-D-glucopyranosylamine

: 408363-46-2
(S)-2-Benzyloxycarbonylamino-3-fluorocarbonyl-propionic acid isobutyl ester

: 408363-43-9
(S)-N-((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-2-benzyloxycarbonylamino-succinamic acid isobutyl ester

Guidance literature:: With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 20 ℃; for 1h;
DOI:10.1055/s-2002-19355

Reference yield:

: 7512-17-6,72-87-7,1136-42-1,1136-44-3,6082-29-7,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4
N-Acetyl-D-glucosamine

: 408363-43-9
(S)-N-((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-2-benzyloxycarbonylamino-succinamic acid isobutyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 87 percent / (NH₄)2CO₃ / dimethylsulfoxide / 1.5 h / 40 °C / 12928.7 Torr / microwave irradiation

2: 62 percent / NaHCO₃ / dimethylformamide / 2.5 h / 20 °C

With ammonium carbonate; sodium hydrogencarbonate; In dimethyl sulfoxide; N,N-dimethyl-formamide; 1: Kochetkov amination;
DOI:10.1021/ol048342n

Reference yield:

: 23632-66-8
(4S)-3-benzyloxycarbonyl-4-carboxymethyl-1,3-oxazolidin-5-one

: 408363-43-9
(S)-N-((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-2-benzyloxycarbonylamino-succinamic acid isobutyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 47 percent / i-BuONa / 3 h / 65 °C

2: 92 percent / cyanuric fluoride; pyridine / CH₂Cl₂

3: 84 percent / NaHCO₃ / dimethylformamide / 1 h / 20 °C

With pyridine; trifluoro-[1,3,5]triazine; sodium isobutoxide; sodium hydrogencarbonate; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1055/s-2002-19355