N-{2-Chloro-5-[(2R,3R,4R,5S,6R)-5-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-pyridin-4-yl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-3,4-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl]-phenyl}-acetamide

Base Information

Chemical Name:N-{2-Chloro-5-[(2R,3R,4R,5S,6R)-5-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-pyridin-4-yl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-3,4-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl]-phenyl}-acetamide
CAS No.:721942-76-3
Molecular Formula:C₂₇H₃₃ClN₂O₁₂
Molecular Weight:613.018
Hs Code.:

N-{2-Chloro-5-[(2R,3R,4R,5S,6R)-5-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-pyridin-4-yl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-3,4-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl]-phenyl}-acetamide

Synonyms:N-{2-Chloro-5-[(2R,3R,4R,5S,6R)-5-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-pyridin-4-yl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-3,4-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl]-phenyl}-acetamide

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Chemical Property of N-{2-Chloro-5-[(2R,3R,4R,5S,6R)-5-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-pyridin-4-yl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-3,4-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl]-phenyl}-acetamide

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Technology Process of N-{2-Chloro-5-[(2R,3R,4R,5S,6R)-5-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-pyridin-4-yl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-3,4-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl]-phenyl}-acetamide

There total 6 articles about N-{2-Chloro-5-[(2R,3R,4R,5S,6R)-5-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-pyridin-4-yl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-3,4-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl]-phenyl}-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: 20.0%

: 872-85-5
pyridine-4-carbaldehyde

: 269734-49-8
3-acetamido-4-chlorobenzyl-β-maltoside

: 721942-76-3
N-{2-Chloro-5-[(2R,3R,4R,5S,6R)-5-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-pyridin-4-yl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-3,4-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl]-phenyl}-acetamide

Guidance literature:: With sulfuric acid; In N,N-dimethyl-formamide; at 110 ℃;
DOI:10.1016/j.bmcl.2004.03.049

Reference yield:

: 55912-20-4
4-chloro-3-nitrobenzyl alcohol

: 721942-76-3
N-{2-Chloro-5-[(2R,3R,4R,5S,6R)-5-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-pyridin-4-yl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-3,4-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl]-phenyl}-acetamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: HgBr₂; Hg(CN)2 / acetonitrile / 0.5 h

1.2: 90 percent / acetonitrile / 18 h / 20 °C

2.1: 96 percent / tin(II) chloride dihydrate / ethyl acetate / 2 h / Heating

3.1: 75 percent / triethylamine / tetrahydrofuran / 6.5 h / 0 - 20 °C

4.1: 99 percent / NaOMe; MeOH / 2.5 h / Heating

5.1: 20 percent / aq. H₂SO₄ / dimethylformamide / 110 °C

With methanol; sulfuric acid; sodium methylate; mercury(II) cyanide; triethylamine; mercury dibromide; tin(ll) chloride; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.bmcl.2004.03.049

Reference yield:

: 4753-07-5,5160-10-1,14206-57-6,14227-66-8,14257-35-3,42385-75-1,67650-37-7,68682-05-3,69308-57-2,69349-74-2,70223-96-0,70223-97-1,71276-38-5,85248-99-3,118493-15-5,120575-76-0
2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-maltosyl bromide

: 721942-76-3
N-{2-Chloro-5-[(2R,3R,4R,5S,6R)-5-((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-pyridin-4-yl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-3,4-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl]-phenyl}-acetamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: HgBr₂; Hg(CN)2 / acetonitrile / 0.5 h

1.2: 90 percent / acetonitrile / 18 h / 20 °C

2.1: 96 percent / tin(II) chloride dihydrate / ethyl acetate / 2 h / Heating

3.1: 75 percent / triethylamine / tetrahydrofuran / 6.5 h / 0 - 20 °C

4.1: 99 percent / NaOMe; MeOH / 2.5 h / Heating

5.1: 20 percent / aq. H₂SO₄ / dimethylformamide / 110 °C

With methanol; sulfuric acid; sodium methylate; mercury(II) cyanide; triethylamine; mercury dibromide; tin(ll) chloride; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.bmcl.2004.03.049