N-[6-(4,5-bis-benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-8-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

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Chemical Name:N-[6-(4,5-bis-benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-8-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide
CAS No.:273749-57-8
Molecular Formula:C₄₂H₅₃NO₁₆
Molecular Weight:827.88
Hs Code.:

<i>N</i>-[6-(4,5-bis-benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-8-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-<i>d</i>][1,3]dioxin-7-yl]-acetamide

Synonyms:N-[6-(4,5-bis-benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-8-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

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Chemical Property of N-[6-(4,5-bis-benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-8-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

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Technology Process of N-[6-(4,5-bis-benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-8-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

There total 10 articles about N-[6-(4,5-bis-benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-8-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-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: 100.0%

: 273749-56-7
methyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)-(4,6-O-benzylidene-2-acetamido-2-deoxy-(β-D-glucopyanosyl)-(1->4)-2,3-di-O-benzyl-β-D-glucopyranoside

: 273749-57-8
N-[6-(4,5-bis-benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-8-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

Guidance literature:: With sodium; In methanol; at 20 ℃; for 12h;
DOI:10.1021/ol0057075

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 273749-57-8
N-[6-(4,5-bis-benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-8-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

Guidance literature:: Multi-step reaction with 6 steps

1: 76 percent / p-TsOH monohydrate / acetonitrile / 0.75 h

2: 84 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 12.5 h / -30 - 20 °C

3: Cd / dimethylformamide; acetic acid / 12 h / 20 °C

4: 160 mg / pyridine / CH₂Cl₂ / 4 h / 20 °C

5: 84 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / acetonitrile; H₂O / 12 h / 0 °C

6: 100 percent / Na / methanol / 12 h / 20 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium; toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; cadmium; In methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetonitrile; 1: Etherification / 2: Condensation / 3: Substitution / 4: Acetylation / 5: Substitution / 6: Deacetylation;
DOI:10.1021/ol0057075

Reference yield:

: 136945-14-7
O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl] trichloroacetimidate

: 273749-57-8
N-[6-(4,5-bis-benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-8-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

Guidance literature:: Multi-step reaction with 8 steps

1: 87 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 4 h / -30 - 20 °C

2: 95 percent / guanidinium nitrate; NaOMe / methanol; CH₂Cl₂ / 0.33 h / 20 °C

3: 76 percent / p-TsOH monohydrate / acetonitrile / 0.75 h

4: 84 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 12.5 h / -30 - 20 °C

5: Cd / dimethylformamide; acetic acid / 12 h / 20 °C

6: 160 mg / pyridine / CH₂Cl₂ / 4 h / 20 °C

7: 84 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / acetonitrile; H₂O / 12 h / 0 °C

8: 100 percent / Na / methanol / 12 h / 20 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; guanidinium nitrate; 4 A molecular sieve; sodium methylate; sodium; toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; cadmium; In methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetonitrile; 1: Condensation / 2: Deacetylation / 3: Etherification / 4: Condensation / 5: Substitution / 6: Acetylation / 7: Substitution / 8: Deacetylation;
DOI:10.1021/ol0057075