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

Base Information

Chemical Name: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
CAS No.:153093-19-7
Molecular Formula:C₅₃H₅₉NO₁₂
Molecular Weight:902.051
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 9 articles about 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 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: 65.0%

: 100-39-0
benzyl bromide

: 153093-17-5
N-[(4aR,6R,7R,8R,8aS)-8-((2R,3R,4S,5S,6R)-4-Allyloxy-3,5-dihydroxy-6-hydroxymethyl-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-[(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

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; for 5h;
DOI:10.1039/c39930001419

Reference yield:

: 529493-92-3
2-(acetoxymethyl)-6-bromotetrahydro-2H-pyran-3,4,5-triyl triacetate

: 153093-19-7
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

Guidance literature:: Multi-step reaction with 4 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

With 4 A molecular sieve; tetrabutylammomium bromide; mercury(II) cyanide; sodium hydride; di(n-butyl)tin oxide; triethylamine; In methanol; nitromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1039/c39930001419

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 153093-19-7
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

Guidance literature:: Multi-step reaction with 5 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

With 4 A molecular sieve; tetrabutylammomium bromide; mercury(II) cyanide; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; nitromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1039/c39930001419