(4aR,6S,6aS,22aS,22bR)-6-Methoxy-2-phenyl-hexadecahydro-1,3,5,7,13,16,22-heptaoxa-10,19-diaza-cyclooctadeca[a]naphthalene-10,19-dicarboxylic acid diethyl ester

Base Information

• Chemical Name: (4aR,6S,6aS,22aS,22bR)-6-Methoxy-2-phenyl-hexadecahydro-1,3,5,7,13,16,22-heptaoxa-10,19-diaza-cyclooctadeca[a]naphthalene-10,19-dicarboxylic acid diethyl ester
• CAS No.: 86545-48-4
• Molecular Formula: C₃₀H₄₆N₂O₁₂
• Molecular Weight: 626.701

Synonyms:(4aR,6S,6aS,22aS,22bR)-6-Methoxy-2-phenyl-hexadecahydro-1,3,5,7,13,16,22-heptaoxa-10,19-diaza-cyclooctadeca[a]naphthalene-10,19-dicarboxylic acid diethyl ester

Chemical Property of (4aR,6S,6aS,22aS,22bR)-6-Methoxy-2-phenyl-hexadecahydro-1,3,5,7,13,16,22-heptaoxa-10,19-diaza-cyclooctadeca[a]naphthalene-10,19-dicarboxylic acid diethyl ester

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Technology Process of (4aR,6S,6aS,22aS,22bR)-6-Methoxy-2-phenyl-hexadecahydro-1,3,5,7,13,16,22-heptaoxa-10,19-diaza-cyclooctadeca[a]naphthalene-10,19-dicarboxylic acid diethyl ester

There total 4 articles about (4aR,6S,6aS,22aS,22bR)-6-Methoxy-2-phenyl-hexadecahydro-1,3,5,7,13,16,22-heptaoxa-10,19-diaza-cyclooctadeca[a]naphthalene-10,19-dicarboxylic acid diethyl ester 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%

N,N'-bisethoxycarbonyl-1,8-diamino-3,6-dioxaoctane (57684-45-4) + methyl 4,6-O-benzylidene-2,3-O-bis(p-toluenesulphonyloxyethyl)-α-D-mannopyranoside (86534-17-0) → (4aR,6S,6aS,22aS,22bR)-6-Methoxy-2-phenyl-hexadecahydro-1,3,5,7,13,16,22-heptaoxa-10,19-diaza-cyclooctadeca[a]naphthalene-10,19-dicarboxylic acid diethyl ester (86545-48-4)

Guidance literature:

With sodium hydride; potassium bromide; In dimethyl sulfoxide; for 72h; Ambient temperature;

DOI:10.1016/S0040-4020(01)91309-2

Reference yield:

(4aR,6S,7S,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol (4148-58-7) → (4aR,6S,6aS,22aS,22bR)-6-Methoxy-2-phenyl-hexadecahydro-1,3,5,7,13,16,22-heptaoxa-10,19-diaza-cyclooctadeca[a]naphthalene-10,19-dicarboxylic acid diethyl ester (86545-48-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / n-Bu₄N⁺HSO₄^-, aq. NaOH (50percent) / benzene / 0.5 h / Ambient temperature

2: 90 percent / LiAlH₄ / diethyl ether / Heating

3: 85 percent / Et₃N / CHCl₃ / 0 °C

4: 60 percent / NaH, KBr / dimethylsulfoxide / 48 h / Ambient temperature

With sodium hydroxide; lithium aluminium tetrahydride; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; triethylamine; potassium bromide; In diethyl ether; chloroform; dimethyl sulfoxide; benzene;

DOI:10.1039/c39830000132

Reference yield:

2-[(4aR,6S,7S,8S,8aR)-7-(2-Hydroxy-ethoxy)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-ethanol (86534-16-9) → (4aR,6S,6aS,22aS,22bR)-6-Methoxy-2-phenyl-hexadecahydro-1,3,5,7,13,16,22-heptaoxa-10,19-diaza-cyclooctadeca[a]naphthalene-10,19-dicarboxylic acid diethyl ester (86545-48-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / Et₃N / CHCl₃ / 0 °C

2: 60 percent / NaH, KBr / dimethylsulfoxide / 48 h / Ambient temperature

With sodium hydride; triethylamine; potassium bromide; In chloroform; dimethyl sulfoxide;

DOI:10.1039/c39830000132

upstream raw materials:

N,N'-bisethoxycarbonyl-1,8-diamino-3,6-dioxaoctane

methyl 4,6-O-benzylidene-2,3-O-bis(p-toluenesulphonyloxyethyl)-α-D-mannopyranoside

(4aR,6S,7S,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

2-[(4aR,6S,7S,8S,8aR)-7-(2-Hydroxy-ethoxy)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-ethanol

Downstream raw materials:

(4aR,6S,6aS,22aS,22bR)-6-Methoxy-10,19-dimethyl-2-phenyl-hexadecahydro-1,3,5,7,13,16,22-heptaoxa-10,19-diaza-cyclooctadeca[a]naphthalene

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