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

Base Information

• Chemical Name: N-[(2R,3R,4R,5S,6R)-4-((2R,3R,4S,5S,6R)-4-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-6-benzyloxymethyl-5-hydroxy-2-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl]-acetamide
• CAS No.: 153093-20-0
• Molecular Formula: C₅₃H₆₁NO₁₂
• Molecular Weight: 904.067

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

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

There total 10 articles about N-[(2R,3R,4R,5S,6R)-4-((2R,3R,4S,5S,6R)-4-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-6-benzyloxymethyl-5-hydroxy-2-(4-methoxy-benzyloxy)-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: 81.0%

N-[(4aR,6R,7R,8R,8aS)-8-((2R,3R,4S,5S,6R)-4-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-6-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide (153093-19-7) → N-[(2R,3R,4R,5S,6R)-4-((2R,3R,4S,5S,6R)-4-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-6-benzyloxymethyl-5-hydroxy-2-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl]-acetamide (153093-20-0)

Guidance literature:

With hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran;

DOI:10.1039/c39930001419

Reference yield:

2-(acetoxymethyl)-6-bromotetrahydro-2H-pyran-3,4,5-triyl triacetate (529493-92-3) → N-[(2R,3R,4R,5S,6R)-4-((2R,3R,4S,5S,6R)-4-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-6-benzyloxymethyl-5-hydroxy-2-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl]-acetamide (153093-20-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / Hg(CN)2, mol. sieve 4A / nitromethane; toluene

2: 93 percent / Et₃N / methanol; H₂O / 48 h / Ambient temperature

3: 1.) 1-Bu₂SnO, 2.) BrNBu₄ / 1.) toluene, 2.) toluene

4: 65 percent / NaH / dimethylformamide / 5 h

5: 81 percent / sodium cyanoborohydride, HCl gas / tetrahydrofuran

With hydrogenchloride; 4 A molecular sieve; tetrabutylammomium bromide; mercury(II) cyanide; sodium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; triethylamine; In tetrahydrofuran; methanol; nitromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1039/c39930001419

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → N-[(2R,3R,4R,5S,6R)-4-((2R,3R,4S,5S,6R)-4-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-6-benzyloxymethyl-5-hydroxy-2-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl]-acetamide (153093-20-0)

Guidance literature:

Multi-step reaction with 6 steps

1: TsOH / tetrahydrofuran

2: 100 percent / Hg(CN)2, mol. sieve 4A / nitromethane; toluene

3: 93 percent / Et₃N / methanol; H₂O / 48 h / Ambient temperature

4: 1.) 1-Bu₂SnO, 2.) BrNBu₄ / 1.) toluene, 2.) toluene

5: 65 percent / NaH / dimethylformamide / 5 h

6: 81 percent / sodium cyanoborohydride, HCl gas / tetrahydrofuran

With hydrogenchloride; 4 A molecular sieve; tetrabutylammomium bromide; mercury(II) cyanide; sodium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; nitromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1039/c39930001419

upstream raw materials:

N-[(4aR,6R,7R,8R,8aS)-8-((2R,3R,4S,5S,6R)-4-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-6-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

2-(acetoxymethyl)-6-bromotetrahydro-2H-pyran-3,4,5-triyl triacetate

benzaldehyde dimethyl acetal

N-[(2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl]-acetamide

Downstream raw materials:

C₇₇H₈₅NO₁₆

C₈₀H₈₉NO₁₆

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