N-{(2S,3R,4R,5S,6R)-2-[(2R,3S,4R,5R,6S)-4,5-Dihydroxy-2-hydroxymethyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide

Base Information

Chemical Name:N-{(2S,3R,4R,5S,6R)-2-[(2R,3S,4R,5R,6S)-4,5-Dihydroxy-2-hydroxymethyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide
CAS No.:22393-17-5
Molecular Formula:C₂₀H₂₈N₂O₁₃
Molecular Weight:504.448
Hs Code.:

N-{(2S,3R,4R,5S,6R)-2-[(2R,3S,4R,5R,6S)-4,5-Dihydroxy-2-hydroxymethyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide

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Chemical Property of N-{(2S,3R,4R,5S,6R)-2-[(2R,3S,4R,5R,6S)-4,5-Dihydroxy-2-hydroxymethyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide

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Technology Process of N-{(2S,3R,4R,5S,6R)-2-[(2R,3S,4R,5R,6S)-4,5-Dihydroxy-2-hydroxymethyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide

There total 3 articles about N-{(2S,3R,4R,5S,6R)-2-[(2R,3S,4R,5R,6S)-4,5-Dihydroxy-2-hydroxymethyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide 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: 2.5%

: 2492-87-7
4-nitrophenyl-β-D-glucoside

: 3459-18-5,50645-66-4
4-nitrophenyl N-acetyl-β-D-glucosaminide

: 22393-17-5
N-{(2S,3R,4R,5S,6R)-2-[(2R,3S,4R,5R,6S)-4,5-Dihydroxy-2-hydroxymethyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide

Guidance literature:: With N-acetyl-β-hexosaminidase (Aspergillus oryzae); at 25 ℃; pH=6.0;
DOI:10.1016/S0040-4039(99)01279-4

Reference yield:

: 250129-85-2
3-nitro-2-pyridyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

: 22393-17-5
N-{(2S,3R,4R,5S,6R)-2-[(2R,3S,4R,5R,6S)-4,5-Dihydroxy-2-hydroxymethyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide

Guidance literature:: Multi-step reaction with 2 steps

1: 84.1 percent / K₂CO₃ / methanol / 2 h

2: 8.6 percent / N-acetyl-β-hexosaminidase (Aspergillus oryzae) / 25 °C / pH 6.0

With N-acetyl-β-hexosaminidase (Aspergillus oryzae); potassium carbonate; In methanol; 1: Deacetylation / 2: transglycosylation;
DOI:10.1016/S0040-4039(99)01279-4

Reference yield:

: 3068-34-6
Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester

: 22393-17-5
N-{(2S,3R,4R,5S,6R)-2-[(2R,3S,4R,5R,6S)-4,5-Dihydroxy-2-hydroxymethyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide

Guidance literature:: Multi-step reaction with 3 steps

1: 28.1 percent / 1M aq. NaOH; Bu₄NBr / CH₂Cl₂ / 0.83 h

2: 84.1 percent / K₂CO₃ / methanol / 2 h

3: 8.6 percent / N-acetyl-β-hexosaminidase (Aspergillus oryzae) / 25 °C / pH 6.0

With sodium hydroxide; N-acetyl-β-hexosaminidase (Aspergillus oryzae); tetrabutylammomium bromide; potassium carbonate; In methanol; dichloromethane; 1: Condensation / 2: Deacetylation / 3: transglycosylation;
DOI:10.1016/S0040-4039(99)01279-4