L-Serine, N-[(1S)-2-methyl-1-[[(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)amino]carbonyl]propyl]-, methyl ester (9CI)

Base Information

Chemical Name:L-Serine, N-[(1S)-2-methyl-1-[[(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)amino]carbonyl]propyl]-, methyl ester (9CI)
CAS No.:236100-70-2
Molecular Formula:C₂₃H₃₆N₂O₁₃
Molecular Weight:548.544
Hs Code.:
Mol file:236100-70-2.mol

Synonyms:L-Serine, N-[(1S)-2-methyl-1-[[(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)amino]carbonyl]propyl]-, methyl ester (9CI)

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Chemical Property of L-Serine, N-[(1S)-2-methyl-1-[[(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)amino]carbonyl]propyl]-, methyl ester (9CI)

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Technology Process of L-Serine, N-[(1S)-2-methyl-1-[[(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)amino]carbonyl]propyl]-, methyl ester (9CI)

There total 3 articles about L-Serine, N-[(1S)-2-methyl-1-[[(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)amino]carbonyl]propyl]-, methyl ester (9CI) 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: 15.0%

: 67-56-1
methanol

: 66118-22-7
(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-isocyanotetrahydro-2H-pyran-3,4,5-triyl triacetate

: 56-45-1,83245-15-2
L-serin

: 78-84-2
isobutyraldehyde

: 213543-33-0,236100-70-2
N-3-methyl-2-[(S)-2-hydroxy-1-methoxycarbonyl-1-ethylamino]-butanoyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl amine

Guidance literature:: With triethylamine; at 55 ℃; for 11h;
DOI:10.1016/S0040-4020(99)00461-5

Reference yield:

: 13992-25-1
1-azido-1-deoxy-β-D-glucopyranoside tetraacetate

: 213543-33-0,236100-70-2
N-3-methyl-2-[(S)-2-hydroxy-1-methoxycarbonyl-1-ethylamino]-butanoyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl amine

Guidance literature:: Multi-step reaction with 3 steps

1.1: H₂ / Pd/C

2.1: ethyl acetate / 7 h / 20 °C

2.2: 65 percent / iPr₂NH; POCl₃ / CH₂Cl₂ / 12 h

3.1: 15 percent / Et₃N / 11 h / 55 °C

With hydrogen; triethylamine; palladium on activated charcoal; In ethyl acetate; 1.1: Hydrogenation / 2.1: Formylation / 2.2: Dehydration / 3.1: Condensation;
DOI:10.1016/S0040-4020(99)00461-5

Reference yield:

: 41355-50-4,51642-81-0,58484-22-3,70128-27-7,70145-20-9,94482-21-0,98300-76-6
2,3,4,6-tetra-O-acetyl-D-glucosyl-1-amine

: 213543-33-0,236100-70-2
N-3-methyl-2-[(S)-2-hydroxy-1-methoxycarbonyl-1-ethylamino]-butanoyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl amine

Guidance literature:: Multi-step reaction with 2 steps

1.1: ethyl acetate / 7 h / 20 °C

1.2: 65 percent / iPr₂NH; POCl₃ / CH₂Cl₂ / 12 h

2.1: 15 percent / Et₃N / 11 h / 55 °C

With triethylamine; In ethyl acetate; 1.1: Formylation / 1.2: Dehydration / 2.1: Condensation;
DOI:10.1016/S0040-4020(99)00461-5