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

Base Information

• Chemical Name: N-<(1RS)-2,3-di-O-acetyl-4,7-O-benzylidene-(1,2,4/3,5,6)-6-chloro-2,3,4 trihydroxy-5-(hydroxymethyl)cyclohexyl>-(1RS)-2,3:4,7-di-O-isopropylidenevalidamine
• CAS No.: 82252-25-3
• Molecular Formula: C₃₁H₄₂ClNO₁₀
• Molecular Weight: 624.128

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

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

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

There total 4 articles about N-<(1RS)-2,3-di-O-acetyl-4,7-O-benzylidene-(1,2,4/3,5,6)-6-chloro-2,3,4 trihydroxy-5-(hydroxymethyl)cyclohexyl>-(1RS)-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: 42.0%

Acetic acid (4aR,5S,7R,8R,8aS)-8-acetoxy-5-hydroxy-2-phenyl-6-((3aR,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-<(1RS)-2,3-di-O-acetyl-4,7-O-benzylidene-(1,2,4/3,5,6)-6-chloro-2,3,4 trihydroxy-5-(hydroxymethyl)cyclohexyl>-(1RS)-2,3:4,7-di-O-isopropylidenevalidamine (82252-25-3) + N-<(1SR)-5,6-di-O-acetyl-4,7O-benzylidene-(1,4,6/5)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexenyl>-(1SR)-2,3:4,7-di-O-isopropylidenevalidamine (82252-27-5) + (1SR)-epimino>-(1SR)-3,4-di-O-acetyl-5,7-O-benzylidene-(1,2,3,5/4,6)-3,4,5-trihydroxy-6-(hydroxymethyl)cyclohexane (82252-26-4)

Guidance literature:

With pyridine; sulfuryl dichloride; Yield given. Further byproducts given. Title compound not separated from byproducts; 1.) -15 degC, 2 h, 2.) 3 degC, overnight;

DOI:10.1021/jo00188a016

Reference yield: 34.0%

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)-5,6-di-O-acetyl-4,7O-benzylidene-(1,4,6/5)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexenyl>-(1SR)-2,3:4,7-di-O-isopropylidenevalidamine (82252-27-5) + (1SR)-epimino>-(1SR)-3,4-di-O-acetyl-5,7-O-benzylidene-(1,2,3,5/4,6)-3,4,5-trihydroxy-6-(hydroxymethyl)cyclohexane (82252-26-4) + Acetic acid (4aR,5R,6R,7S,8S,8aR)-8-acetoxy-5-chloro-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 (82252-25-3)

Guidance literature:

With pyridine; sulfuryl dichloride; 1.) -15 deg C, 2 h; 2.) 3 deg C;

DOI:10.1246/cl.1982.749

Reference yield: 21.0%

Acetic acid (4aR,5S,7R,8R,8aS)-8-acetoxy-5-hydroxy-2-phenyl-6-((3aR,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-<(1RS)-2,3-di-O-acetyl-4,7-O-benzylidene-(1,2,4/3,5,6)-6-chloro-2,3,4 trihydroxy-5-(hydroxymethyl)cyclohexyl>-(1RS)-2,3:4,7-di-O-isopropylidenevalidamine (82252-25-3) + (1SR)-epimino>-(1SR)-3,4-di-O-acetyl-5,7-O-benzylidene-(1,2,3,5/4,6)-3,4,5-trihydroxy-6-(hydroxymethyl)cyclohexane (82252-26-4)

Guidance literature:

With pyridine; methanesulfonyl chloride; Further byproducts given; 1.) 0 degC, 1 h, 2.) 3 degC, overnight;

DOI:10.1021/jo00188a016

upstream raw materials:

Acetic acid (4aR,5S,7R,8R,8aS)-8-acetoxy-5-hydroxy-2-phenyl-6-((3aR,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

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

Downstream raw materials:

Acetic acid (6R,7R,8R,8aS)-8-acetoxy-2-phenyl-6-((3aR,4S,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)-6,7,8,8a-tetrahydro-4H-benzo[1,3]dioxin-7-yl ester

(1SR)-epimino>-(1RS)-3,4-di-O-acetyl-5,7-O-benzylidene-(1,2,3,5/4,6)-3,4,5-trihydroxy-6-(hydroxymethyl)cyclohexane

Acetic acid (6S,7S,8S,8aR)-8-acetoxy-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)-6,7,8,8a-tetrahydro-4H-benzo[1,3]dioxin-7-yl ester

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