(1S,2S,4R,18S,20R,23R)-9-hydroxy-23-methoxy-21-oxa-6,16-diazahexacyclo[18.2.1.0²'¹⁸.0⁴'¹⁶.0⁵'¹³.0⁷'¹²]tricosa-5⁽¹³⁾,7,9,11-tetraen-22-one

Base Information

• Chemical Name: (1S,2S,4R,18S,20R,23R)-9-hydroxy-23-methoxy-21-oxa-6,16-diazahexacyclo[18.2.1.0²'¹⁸.0⁴'¹⁶.0⁵'¹³.0⁷'¹²]tricosa-5⁽¹³⁾,7,9,11-tetraen-22-one
• CAS No.: 866412-74-0
• Molecular Formula: C₂₁H₂₄N₂O₄
• Molecular Weight: 368.433

Synonyms:(1S,2S,4R,18S,20R,23R)-9-hydroxy-23-methoxy-21-oxa-6,16-diazahexacyclo[18.2.1.0²'¹⁸.0⁴'¹⁶.0⁵'¹³.0⁷'¹²]tricosa-5⁽¹³⁾,7,9,11-tetraen-22-one

Chemical Property of (1S,2S,4R,18S,20R,23R)-9-hydroxy-23-methoxy-21-oxa-6,16-diazahexacyclo[18.2.1.0²'¹⁸.0⁴'¹⁶.0⁵'¹³.0⁷'¹²]tricosa-5⁽¹³⁾,7,9,11-tetraen-22-one

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Technology Process of (1S,2S,4R,18S,20R,23R)-9-hydroxy-23-methoxy-21-oxa-6,16-diazahexacyclo[18.2.1.0²'¹⁸.0⁴'¹⁶.0⁵'¹³.0⁷'¹²]tricosa-5⁽¹³⁾,7,9,11-tetraen-22-one

There total 2 articles about (1S,2S,4R,18S,20R,23R)-9-hydroxy-23-methoxy-21-oxa-6,16-diazahexacyclo[18.2.1.0²'¹⁸.0⁴'¹⁶.0⁵'¹³.0⁷'¹²]tricosa-5⁽¹³⁾,7,9,11-tetraen-22-one 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: 85.0%

11-O-p-toluenesulfonylreserpic acid lactone (866412-75-1) → (1S,2S,4R,18S,20R,23R)-9-hydroxy-23-methoxy-21-oxa-6,16-diazahexacyclo[18.2.1.02'18.04'16.05'13.07'12]tricosa-5(13),7,9,11-tetraen-22-one (866412-74-0) + deserpidic acid lactone (6696-77-1)

Guidance literature:

With hydrogen; In tetrahydrofuran; ethanol; for 8h; under 2585.81 Torr;

DOI:10.1021/np050179x

Reference yield: 60.0%

11-O-methanesulfonylreserpic acid lactone (872458-59-8) → (1S,2S,4R,18S,20R,23R)-9-hydroxy-23-methoxy-21-oxa-6,16-diazahexacyclo[18.2.1.02'18.04'16.05'13.07'12]tricosa-5(13),7,9,11-tetraen-22-one (866412-74-0) + deserpidic acid lactone (6696-77-1)

Guidance literature:

With hydrogen; In tetrahydrofuran; ethanol; for 8h; under 2585.81 Torr;

DOI:10.1021/np050179x

Reference yield: 76.0%

(1S,2S,4R,18S,20R,23R)-9-hydroxy-23-methoxy-21-oxa-6,16-diazahexacyclo[18.2.1.02'18.04'16.05'13.07'12]tricosa-5(13),7,9,11-tetraen-22-one (866412-74-0) + p-toluenesulfonyl chloride (98-59-9) → 11-O-p-toluenesulfonylreserpic acid lactone (866412-75-1)

Guidance literature:

With triethylamine; In tetrahydrofuran; for 42h; Heating;

DOI:10.1021/np050179x

upstream raw materials:

11-O-methanesulfonylreserpic acid lactone

11-O-p-toluenesulfonylreserpic acid lactone

Downstream raw materials:

11-O-p-toluenesulfonylreserpic acid lactone

methyl (1R,15S,17R,18R,19S,20S)-6-{[(tert-butoxy)carbonyl]oxy}-17-({4-[(ethoxycarbonyl)oxy]-3,5-dimethoxyphenyl}carbonyloxy)-18-methoxy-3,13-diazapentacyclo[11.8.0.0^2,10.0^4,9.0^15,20]henicosa-2⁽¹⁰⁾,4,6,8-tetraene-19-carboxylate

methyl (1R,15S,17R,18R,19S,20S)-17-({4-[(ethoxycarbonyl)oxy]-3,5-dimethoxyphenyl}carbonyloxy)-6-hydroxy-18-methoxy-3,13-diazapentacyclo[11.8.0.0^2,10.0^4,9.0^15,20]henicosa-2⁽¹⁰⁾,4,6,8-tetraene-19-carboxylate

methyl (1R,15S,17R,18R,19S,20S)-6-(acetyloxy)-17-({4-[(ethoxycarbonyl)oxy]-3,5-dimethoxyphenyl}carbonyloxy)-18-methoxy-3,13-diazapentacyclo[11.8.0.0^2,10.0^4,9.0^15,20]henicosa-2⁽¹⁰⁾,4,6,8-tetraene-19-carboxylate

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