N-[5-(6-azidomethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-(4,5-bis-benzyloxy-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl]-propionamide

Base Information

Chemical Name:N-[5-(6-azidomethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-(4,5-bis-benzyloxy-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl]-propionamide
CAS No.:629620-28-6
Molecular Formula:C₆₄H₈₂N₄O₁₅
Molecular Weight:1147.37
Hs Code.:

<i>N</i>-[5-(6-azidomethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-(4,5-bis-benzyloxy-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl]-propionamide

Synonyms:N-[5-(6-azidomethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-(4,5-bis-benzyloxy-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl]-propionamide

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Chemical Property of N-[5-(6-azidomethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-(4,5-bis-benzyloxy-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl]-propionamide

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Technology Process of N-[5-(6-azidomethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-(4,5-bis-benzyloxy-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl]-propionamide

There total 8 articles about N-[5-(6-azidomethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-(4,5-bis-benzyloxy-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl]-propionamide 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: 79.0%

: 629620-27-5
octyl (6-azido-6-deoxy-2,3,4-tri-O-propionyl-β-D-galactopyranosyl)-(1->4)-(3,6-di-O-benzyl-2-deoxy-2-propionamido-β-D-glucopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

: 629620-28-6
N-[5-(6-azidomethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-(4,5-bis-benzyloxy-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl]-propionamide

Guidance literature:: With sodium methylate; In methanol; for 2.5h; pH=9;
DOI:10.1002/ejoc.200300293

Reference yield:

: 4711-00-6
6-azido-6-deoxy-1,2:3,4-di-O-isopropylidene-D-galactopyranose

: 629620-28-6
N-[5-(6-azidomethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-(4,5-bis-benzyloxy-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl]-propionamide

Guidance literature:: Multi-step reaction with 8 steps

1: trifluoroacetic acid; water / 2 h

2: 583 mg / pyridine

3: 89 percent / hydrazinium acetate / dimethylformamide / 1.17 h / 50 °C

4: 63 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h

5: 61 percent / TMSOTf; Ms 4A / CH₂Cl₂ / 0 °C

6: 3A MS; 1,2-diaminoethane / butan-1-ol / 90 °C

7: 91 mg / pyridine

8: 79 percent / NaOMe / methanol / 2.5 h / pH 9

With pyridine; trimethylsilyl trifluoromethanesulfonate; water; sodium methylate; hydrazinium monoacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; ethylenediamine; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; butan-1-ol;
DOI:10.1002/ejoc.200300293

Reference yield:

: 4478-43-7
(1,2:3,4-di-O-isopropylidene-6-O-(p-toluensulfonate))-D-galactopiranose

: 629620-28-6
N-[5-(6-azidomethyl-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-(4,5-bis-benzyloxy-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl]-propionamide

Guidance literature:: Multi-step reaction with 9 steps

1: 99 percent / NaN₃ / dimethylsulfoxide / 2 h / 160 °C

2: trifluoroacetic acid; water / 2 h

3: 583 mg / pyridine

4: 89 percent / hydrazinium acetate / dimethylformamide / 1.17 h / 50 °C

5: 63 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h

6: 61 percent / TMSOTf; Ms 4A / CH₂Cl₂ / 0 °C

7: 3A MS; 1,2-diaminoethane / butan-1-ol / 90 °C

8: 91 mg / pyridine

9: 79 percent / NaOMe / methanol / 2.5 h / pH 9

With pyridine; sodium azide; trimethylsilyl trifluoromethanesulfonate; water; sodium methylate; hydrazinium monoacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; ethylenediamine; trifluoroacetic acid; In methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; butan-1-ol;
DOI:10.1002/ejoc.200300293