N-{(2S,3R,4R,5S,6R)-5-((2S,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-benzyloxy-6-benzyloxymethyl-4-[((E)-but-2-enyl)oxy]-tetrahydro-pyran-3-yl}-acetamide

Base Information

Chemical Name:N-{(2S,3R,4R,5S,6R)-5-((2S,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-benzyloxy-6-benzyloxymethyl-4-[((E)-but-2-enyl)oxy]-tetrahydro-pyran-3-yl}-acetamide
CAS No.:83100-68-9
Molecular Formula:C₃₄H₄₆N₂O₁₁
Molecular Weight:658.746
Hs Code.:

N-{(2S,3R,4R,5S,6R)-5-((2S,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-benzyloxy-6-benzyloxymethyl-4-[((E)-but-2-enyl)oxy]-tetrahydro-pyran-3-yl}-acetamide

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Chemical Property of N-{(2S,3R,4R,5S,6R)-5-((2S,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-benzyloxy-6-benzyloxymethyl-4-[((E)-but-2-enyl)oxy]-tetrahydro-pyran-3-yl}-acetamide

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Technology Process of N-{(2S,3R,4R,5S,6R)-5-((2S,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-benzyloxy-6-benzyloxymethyl-4-[((E)-but-2-enyl)oxy]-tetrahydro-pyran-3-yl}-acetamide

There total 8 articles about N-{(2S,3R,4R,5S,6R)-5-((2S,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-benzyloxy-6-benzyloxymethyl-4-[((E)-but-2-enyl)oxy]-tetrahydro-pyran-3-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:

: 75957-41-4
benzyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-6-O-benzyl-3-O-(2-butenyl)-2-deoxy-α-D-glucopyranoside

: 83100-68-9
N-{(2S,3R,4R,5S,6R)-5-((2S,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-benzyloxy-6-benzyloxymethyl-4-[((E)-but-2-enyl)oxy]-tetrahydro-pyran-3-yl}-acetamide

Guidance literature:: With sodium methylate; In methanol;
DOI:10.1016/S0008-6215(00)82587-2

Reference yield:

: 66026-10-6
N-((4aR,6S,7R,8R,8aS)-6-(benzyloxy)-8-hydroxy-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)acetamide

: 83100-68-9
N-{(2S,3R,4R,5S,6R)-5-((2S,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-benzyloxy-6-benzyloxymethyl-4-[((E)-but-2-enyl)oxy]-tetrahydro-pyran-3-yl}-acetamide

Guidance literature:: Multi-step reaction with 7 steps

1: 76.4 percent / barium oxide, barium hydroxide octahydrate / dimethylformamide / 36 h / 0 - 22 °C

2: 96.4 percent / 60percent acetic acid / H₂O / 3 h / 60 °C

3: 82 percent / pyridine / 1 h / -20 °C

4: p-TsOH*H₂O / dioxane / 3 h / Ambient temperature

5: 1.) barium oxide, barium hydroxide octahydrate; 2.) 70percent acetic acid / 1.) N,N-dimethylformamide, 0 deg C, room temperature, 18 h; 2.) water, 50 deg C, 4 h

6: 36.1 percent / p-TsOH / 1,2-dichloro-ethane / 10 h / Heating

7: 467 mg / sodium methoxide / methanol

With pyridine; barium hydroxide octahydrate; sodium methylate; toluene-4-sulfonic acid; acetic acid; barium(II) oxide; In 1,4-dioxane; methanol; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(00)82587-2

Reference yield:

: 83100-64-5
N-{(2S,3R,4R,5S,6R)-2-Benzyloxy-4-[((E)-but-2-enyl)oxy]-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide

: 83100-68-9
N-{(2S,3R,4R,5S,6R)-5-((2S,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-benzyloxy-6-benzyloxymethyl-4-[((E)-but-2-enyl)oxy]-tetrahydro-pyran-3-yl}-acetamide

Guidance literature:: Multi-step reaction with 5 steps

1: 82 percent / pyridine / 1 h / -20 °C

2: p-TsOH*H₂O / dioxane / 3 h / Ambient temperature

3: 1.) barium oxide, barium hydroxide octahydrate; 2.) 70percent acetic acid / 1.) N,N-dimethylformamide, 0 deg C, room temperature, 18 h; 2.) water, 50 deg C, 4 h

4: 36.1 percent / p-TsOH / 1,2-dichloro-ethane / 10 h / Heating

5: 467 mg / sodium methoxide / methanol

With pyridine; barium hydroxide octahydrate; sodium methylate; toluene-4-sulfonic acid; acetic acid; barium(II) oxide; In 1,4-dioxane; methanol; 1,2-dichloro-ethane;
DOI:10.1016/S0008-6215(00)82587-2