3-{3-acetylamino-6-[3-acetylamino-4-hydroxy-6-hydroxymethyl-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxymethyl]-4,5-dihydroxy-tetrahydro-pyran-2-yloxy}-2-benzyloxycarbonylamino-propionic acid

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Chemical Name:3-{3-acetylamino-6-[3-acetylamino-4-hydroxy-6-hydroxymethyl-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxymethyl]-4,5-dihydroxy-tetrahydro-pyran-2-yloxy}-2-benzyloxycarbonylamino-propionic acid
CAS No.:729602-89-5
Molecular Formula:C₃₃H₄₉N₃O₂₀
Molecular Weight:807.76
Hs Code.:

3-{3-acetylamino-6-[3-acetylamino-4-hydroxy-6-hydroxymethyl-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxymethyl]-4,5-dihydroxy-tetrahydro-pyran-2-yloxy}-2-benzyloxycarbonylamino-propionic acid

Synonyms:3-{3-acetylamino-6-[3-acetylamino-4-hydroxy-6-hydroxymethyl-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxymethyl]-4,5-dihydroxy-tetrahydro-pyran-2-yloxy}-2-benzyloxycarbonylamino-propionic acid

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Chemical Property of 3-{3-acetylamino-6-[3-acetylamino-4-hydroxy-6-hydroxymethyl-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxymethyl]-4,5-dihydroxy-tetrahydro-pyran-2-yloxy}-2-benzyloxycarbonylamino-propionic acid

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Technology Process of 3-{3-acetylamino-6-[3-acetylamino-4-hydroxy-6-hydroxymethyl-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxymethyl]-4,5-dihydroxy-tetrahydro-pyran-2-yloxy}-2-benzyloxycarbonylamino-propionic acid

There total 10 articles about 3-{3-acetylamino-6-[3-acetylamino-4-hydroxy-6-hydroxymethyl-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxymethyl]-4,5-dihydroxy-tetrahydro-pyran-2-yloxy}-2-benzyloxycarbonylamino-propionic acid 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: 95.0%

: 729602-88-4
2-benzyloxycarbonylamino-3-{4,5-diacetoxy-6-[4-acetoxy-3-acetylamino-6-hydroxymethyl-5-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxymethyl]-3-acetylamino-tetrahydro-pyran-2-yloxy}-propionic acid methyl ester

: 729602-89-5
3-{3-acetylamino-6-[3-acetylamino-4-hydroxy-6-hydroxymethyl-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxymethyl]-4,5-dihydroxy-tetrahydro-pyran-2-yloxy}-2-benzyloxycarbonylamino-propionic acid

Guidance literature:: With sodium methylate; In methanol; water; at 50 ℃; for 30h; pH=10;
DOI:10.1021/ol0493195

Reference yield:

: 74084-36-9
3-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serine methyl ester

: 729602-89-5
3-{3-acetylamino-6-[3-acetylamino-4-hydroxy-6-hydroxymethyl-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxymethyl]-4,5-dihydroxy-tetrahydro-pyran-2-yloxy}-2-benzyloxycarbonylamino-propionic acid

Guidance literature:: Multi-step reaction with 8 steps

1.1: 90 percent / Et₃N / methanol / 16 h

2.1: 84 percent / (1R)-(-)-camphorsulfonic acid / dimethylformamide / 4 h / 50 °C

3.1: 70 percent / NIS; TfOH / CH₂Cl₂ / 0.5 h / 0 °C

4.1: AcOH / H₂O / 3 h / 80 °C

4.2: 80 percent / pyridine / 16 h

5.1: 95 percent / pyridine / 16 h

6.1: 80 percent / AcOH; Zn / 16 h

7.1: 81 percent / AcOH; TBAF / 24 h / 0 - 20 °C

8.1: 95 percent / NaOMe / methanol; H₂O / 30 h / 50 °C / pH 10

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; (R)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; sodium methylate; acetic acid; triethylamine; zinc; In methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ol0493195

Reference yield:

: 729602-72-6
Cbz-Ser(2-azido-2-deoxy-α-D-galactopyranoside)-OMe

: 729602-89-5
3-{3-acetylamino-6-[3-acetylamino-4-hydroxy-6-hydroxymethyl-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxymethyl]-4,5-dihydroxy-tetrahydro-pyran-2-yloxy}-2-benzyloxycarbonylamino-propionic acid

Guidance literature:: Multi-step reaction with 7 steps

1.1: 84 percent / (1R)-(-)-camphorsulfonic acid / dimethylformamide / 4 h / 50 °C

2.1: 70 percent / NIS; TfOH / CH₂Cl₂ / 0.5 h / 0 °C

3.1: AcOH / H₂O / 3 h / 80 °C

3.2: 80 percent / pyridine / 16 h

4.1: 95 percent / pyridine / 16 h

5.1: 80 percent / AcOH; Zn / 16 h

6.1: 81 percent / AcOH; TBAF / 24 h / 0 - 20 °C

7.1: 95 percent / NaOMe / methanol; H₂O / 30 h / 50 °C / pH 10

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; (R)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; sodium methylate; acetic acid; zinc; In methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ol0493195