N-[(2R,3R,4R,5S,6R)-2-[2-(2-Azido-ethoxy)-ethoxy]-6-benzyloxymethyl-5-((2S,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-4-hydroxy-tetrahydro-pyran-3-yl]-acetamide

Base Information

• Chemical Name: N-[(2R,3R,4R,5S,6R)-2-[2-(2-Azido-ethoxy)-ethoxy]-6-benzyloxymethyl-5-((2S,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-4-hydroxy-tetrahydro-pyran-3-yl]-acetamide
• CAS No.: 213192-07-5
• Molecular Formula: C₄₆H₅₆N₄O₁₂
• Molecular Weight: 856.97

Synonyms:N-[(2R,3R,4R,5S,6R)-2-[2-(2-Azido-ethoxy)-ethoxy]-6-benzyloxymethyl-5-((2S,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-4-hydroxy-tetrahydro-pyran-3-yl]-acetamide

Chemical Property of N-[(2R,3R,4R,5S,6R)-2-[2-(2-Azido-ethoxy)-ethoxy]-6-benzyloxymethyl-5-((2S,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-4-hydroxy-tetrahydro-pyran-3-yl]-acetamide

Chemical Property:

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Technology Process of N-[(2R,3R,4R,5S,6R)-2-[2-(2-Azido-ethoxy)-ethoxy]-6-benzyloxymethyl-5-((2S,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-4-hydroxy-tetrahydro-pyran-3-yl]-acetamide

There total 11 articles about N-[(2R,3R,4R,5S,6R)-2-[2-(2-Azido-ethoxy)-ethoxy]-6-benzyloxymethyl-5-((2S,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-4-hydroxy-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: 96.0%

Acetic acid (2S,3R,4S,5S,6R)-2-{(2R,3S,4R,5R,6R)-5-acetylamino-6-[2-(2-azido-ethoxy)-ethoxy]-2-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yloxy}-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester (213192-06-4) → N-[(2R,3R,4R,5S,6R)-2-[2-(2-Azido-ethoxy)-ethoxy]-6-benzyloxymethyl-5-((2S,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-4-hydroxy-tetrahydro-pyran-3-yl]-acetamide (213192-07-5)

Guidance literature:

With sodium methylate; In methanol; for 16h;

DOI:10.1080/07328309808007459

Reference yield:

benzaldehyde (100-52-7) → N-[(2R,3R,4R,5S,6R)-2-[2-(2-Azido-ethoxy)-ethoxy]-6-benzyloxymethyl-5-((2S,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-4-hydroxy-tetrahydro-pyran-3-yl]-acetamide (213192-07-5)

Guidance literature:

Multi-step reaction with 6 steps

1: ZnCl₂ / 24 h

2: 83.2 percent / BaO, Ba(OH)2*8H₂O / dimethylformamide; CH₂Cl₂ / 1 h / Heating

3: 56 percent / NaBH₃CN / tetrahydrofuran / 0.25 h / Ambient temperature

4: 57 percent / AgOTf, iPr₂Et / CH₂Cl₂ / 6 h / Ambient temperature

5: 83 percent / DDQ / CH₂Cl₂; H₂O / 0.33 h / Ambient temperature

6: 96 percent / NaOMe / methanol / 16 h

With barium dihydroxide; sodium methylate; silver trifluoromethanesulfonate; sodium cyanoborohydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) chloride; barium(II) oxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1080/07328309808007459

Reference yield:

N-{(2R,3R,4R,5S,6R)-2-[2-(2-Azido-ethoxy)-ethoxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide (338971-32-7) → N-[(2R,3R,4R,5S,6R)-2-[2-(2-Azido-ethoxy)-ethoxy]-6-benzyloxymethyl-5-((2S,3R,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-4-hydroxy-tetrahydro-pyran-3-yl]-acetamide (213192-07-5)

Guidance literature:

Multi-step reaction with 6 steps

1: ZnCl₂ / 24 h

2: 83.2 percent / BaO, Ba(OH)2*8H₂O / dimethylformamide; CH₂Cl₂ / 1 h / Heating

3: 56 percent / NaBH₃CN / tetrahydrofuran / 0.25 h / Ambient temperature

4: 57 percent / AgOTf, iPr₂Et / CH₂Cl₂ / 6 h / Ambient temperature

5: 83 percent / DDQ / CH₂Cl₂; H₂O / 0.33 h / Ambient temperature

6: 96 percent / NaOMe / methanol / 16 h

With barium dihydroxide; sodium methylate; silver trifluoromethanesulfonate; sodium cyanoborohydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) chloride; barium(II) oxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1080/07328309808007459

upstream raw materials:

Acetic acid (2S,3R,4S,5S,6R)-2-{(2R,3S,4R,5R,6R)-5-acetylamino-6-[2-(2-azido-ethoxy)-ethoxy]-2-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yloxy}-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

benzaldehyde

N-{(2R,3R,4R,5S,6R)-2-[2-(2-Azido-ethoxy)-ethoxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide

N-{(4aR,6R,7R,8R,8aS)-6-[2-(2-Azido-ethoxy)-ethoxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

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