N-<(1SR)-2,3,6-tri-O-acetyl-4,7-O-benzylidene-(1,2,4/3,5,6)-2,3,4,6-tetrahydroxy-5-(hydroxymethyl)cyclohexyl>-(1SR)-2,3:4,7-di-O-isopropylidenevalidamine

Base Information

• Chemical Name: N-<(1SR)-2,3,6-tri-O-acetyl-4,7-O-benzylidene-(1,2,4/3,5,6)-2,3,4,6-tetrahydroxy-5-(hydroxymethyl)cyclohexyl>-(1SR)-2,3:4,7-di-O-isopropylidenevalidamine
• CAS No.: 82252-24-2
• Molecular Formula: C₃₃H₄₅NO₁₂
• Molecular Weight: 647.72

Synonyms:N-<(1SR)-2,3,6-tri-O-acetyl-4,7-O-benzylidene-(1,2,4/3,5,6)-2,3,4,6-tetrahydroxy-5-(hydroxymethyl)cyclohexyl>-(1SR)-2,3:4,7-di-O-isopropylidenevalidamine

Chemical Property of N-<(1SR)-2,3,6-tri-O-acetyl-4,7-O-benzylidene-(1,2,4/3,5,6)-2,3,4,6-tetrahydroxy-5-(hydroxymethyl)cyclohexyl>-(1SR)-2,3:4,7-di-O-isopropylidenevalidamine

Chemical Property:

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Technology Process of N-<(1SR)-2,3,6-tri-O-acetyl-4,7-O-benzylidene-(1,2,4/3,5,6)-2,3,4,6-tetrahydroxy-5-(hydroxymethyl)cyclohexyl>-(1SR)-2,3:4,7-di-O-isopropylidenevalidamine

There total 8 articles about N-<(1SR)-2,3,6-tri-O-acetyl-4,7-O-benzylidene-(1,2,4/3,5,6)-2,3,4,6-tetrahydroxy-5-(hydroxymethyl)cyclohexyl>-(1SR)-2,3:4,7-di-O-isopropylidenevalidamine 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: 39.0%

acetic anhydride (108-24-7) + N-<(1SR)-2,3-di-O-acetyl-4,7-O-benzylidene-(1,2,4/3,5,6)-2,3,4,6-tetrahydroxy-5-(hydroxymethyl)cyclohexyl>-(1SR)-2,3:4,7-di-O-isopropylidenevalidamine (82252-22-0) → Acetic acid (4aS,5R,6S,7S,8S,8aR)-7,8-diacetoxy-2-phenyl-6-((3aS,4R,5aR,9aR,9bS)-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-ylamino)-hexahydro-benzo[1,3]dioxin-5-yl ester (82252-24-2) + N-<(1SR)-2,3,6-tri-O-acetyl-4,7-O-benzylidene-(1,2,4/3,5,6)-2,3,4,6-tetrahydroxy-5-(hydroxymethyl)cyclohexyl>-(1SR)-2,3:4,7-di-O-isopropylidenevalidamine (82252-24-2)

Guidance literature:

With pyridine; ambient temp.; overnight;

DOI:10.1021/jo00188a016

Reference yield: 39.0%

acetic anhydride (108-24-7) + N-<(1SR)-2,3-di-O-acetyl-4,7-O-benzylidene-(1,2,4/3,5,6)-2,3,4,6-tetrahydroxy-5-(hydroxymethyl)cyclohexyl>-(1SR)-2,3:4,7-di-O-isopropylidenevalidamine (82252-22-0) → Acetic acid (4aS,5R,6S,7S,8S,8aR)-7,8-diacetoxy-2-phenyl-6-((3aS,4R,5aR,9aR,9bS)-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-ylamino)-hexahydro-benzo[1,3]dioxin-5-yl ester (82252-24-2) + N-<(1SR)-2,3,6-tri-O-acetyl-4,7-O-benzylidene-(1,2,4/3,5,6)-2,3,4,6-tetrahydroxy-5-(hydroxymethyl)cyclohexyl>-(1SR)-2,3:4,7-di-O-isopropylidenevalidamine (82252-24-2)

Guidance literature:

With pyridine; ambient temp.; overnight;

DOI:10.1021/jo00188a016

Reference yield: 14.0%

Acetic acid 8-acetoxy-5-hydroxy-2-phenyl-6-((3aR,4R,5aS,9aS,9bR)-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-ylamino)-hexahydro-benzo[1,3]dioxin-7-yl ester (82252-22-0) → N-<(1SR)-2,3,6-tri-O-acetyl-4,7-O-benzylidene-(1,2,4/3,5,6)-2,3,4,6-tetrahydroxy-5-(hydroxymethyl)cyclohexyl>-(1SR)-2,3:4,7-di-O-isopropylidenevalidamine (82252-24-2) + Acetic acid (4aS,5R,6S,7S,8S,8aR)-7,8-diacetoxy-2-phenyl-6-((3aR,4R,5aS,9aS,9bR)-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-ylamino)-hexahydro-benzo[1,3]dioxin-5-yl ester (82252-24-2)

Guidance literature:

With acetylation reagents;

DOI:10.1246/cl.1982.749

upstream raw materials:

acetic anhydride

N-<(1SR)-2,3-di-O-acetyl-4,7-O-benzylidene-(1,2,4/3,5,6)-2,3,4,6-tetrahydroxy-5-(hydroxymethyl)cyclohexyl>-(1SR)-2,3:4,7-di-O-isopropylidenevalidamine

Acetic acid 8-acetoxy-5-hydroxy-2-phenyl-6-((3aR,4R,5aS,9aS,9bR)-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-ylamino)-hexahydro-benzo[1,3]dioxin-7-yl ester

DL-3,4-di-O-acetyl-1,2-anhydro-5,7-O-benzylidene-(1,2,4,6/3,5)-6-hydroxymethyl-1,2,3,4,5-cyclohexanepentol

Downstream raw materials:

Acetic acid (1R,2R,3S,4R,5S,6R)-2,3,5-triacetoxy-4-acetoxymethyl-6-((1S,2R,3R,4S,5S)-2,3,4-triacetoxy-5-acetoxymethyl-cyclohexylamino)-cyclohexyl ester

Acetic acid (1R,2R,3S,4R,5S,6R)-2,3,5-triacetoxy-4-acetoxymethyl-6-((1R,2R,3R,4S,5S)-2,3,4-triacetoxy-5-acetoxymethyl-cyclohexylamino)-cyclohexyl ester

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