Carbonic acid (14E,16E)-(6R,8S,9R,10S)-22-chloro-13,21-dimethoxy-2,6,9,17-tetramethyl-3,5,12-trioxo-7-oxa-2-aza-tricyclo[17.3.1.0^6,8]tricosa-1⁽²³⁾,14,16,19,21-pentaen-10-yl ester phenyl ester

Base Information

• Chemical Name: Carbonic acid (14E,16E)-(6R,8S,9R,10S)-22-chloro-13,21-dimethoxy-2,6,9,17-tetramethyl-3,5,12-trioxo-7-oxa-2-aza-tricyclo[17.3.1.0^6,8]tricosa-1⁽²³⁾,14,16,19,21-pentaen-10-yl ester phenyl ester
• CAS No.: 75448-81-6
• Molecular Formula: C₃₄H₃₈ClNO₉
• Molecular Weight: 640.13
• Mol file: 75448-81-6.mol

Synonyms:

Chemical Property of Carbonic acid (14E,16E)-(6R,8S,9R,10S)-22-chloro-13,21-dimethoxy-2,6,9,17-tetramethyl-3,5,12-trioxo-7-oxa-2-aza-tricyclo[17.3.1.0^6,8]tricosa-1⁽²³⁾,14,16,19,21-pentaen-10-yl ester phenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Carbonic acid (14E,16E)-(6R,8S,9R,10S)-22-chloro-13,21-dimethoxy-2,6,9,17-tetramethyl-3,5,12-trioxo-7-oxa-2-aza-tricyclo[17.3.1.0^6,8]tricosa-1⁽²³⁾,14,16,19,21-pentaen-10-yl ester phenyl ester

There total 7 articles about Carbonic acid (14E,16E)-(6R,8S,9R,10S)-22-chloro-13,21-dimethoxy-2,6,9,17-tetramethyl-3,5,12-trioxo-7-oxa-2-aza-tricyclo[17.3.1.0^6,8]tricosa-1⁽²³⁾,14,16,19,21-pentaen-10-yl ester phenyl 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:

(14E,16E)-(6R,8S,9R,10S)-22-Chloro-10-hydroxy-13,21-dimethoxy-2,6,9,17-tetramethyl-7-oxa-2-aza-tricyclo[17.3.1.06,8]tricosa-1(23),14,16,19,21-pentaene-3,5,12-trione (75448-80-5,75494-70-1) + phenyl chloroformate (1885-14-9) → Carbonic acid (14E,16E)-(6R,8S,9R,10S)-22-chloro-13,21-dimethoxy-2,6,9,17-tetramethyl-3,5,12-trioxo-7-oxa-2-aza-tricyclo[17.3.1.06,8]tricosa-1(23),14,16,19,21-pentaen-10-yl ester phenyl ester (75448-81-6,75494-71-2)

Guidance literature:

With pyridine; In tetrahydrofuran; diethyl ether; at 0 ℃; for 1h;

DOI:10.1021/ja00541a054

Reference yield:

N-{2-Chloro-5-[(2E,4E)-(9R,10S)-9-(1-ethoxy-ethoxy)-7,7-bis-ethylsulfanyl-10-((2R,3S)-3-formyl-3-methyl-oxiranyl)-6-methoxy-2-methyl-undeca-2,4-dienyl]-3-methoxy-phenyl}-N-methyl-acetamide (75448-83-8,75494-72-3,75494-73-4,75494-74-5) → Carbonic acid (14E,16E)-(6R,8S,9R,10S)-22-chloro-13,21-dimethoxy-2,6,9,17-tetramethyl-3,5,12-trioxo-7-oxa-2-aza-tricyclo[17.3.1.06,8]tricosa-1(23),14,16,19,21-pentaen-10-yl ester phenyl ester (75448-81-6,75494-71-2)

Guidance literature:

Multi-step reaction with 6 steps

1: AgNO₃, aq. NaOH / tetrahydrofuran / 2 h / 25 °C

2: diethyl ether / 0 °C

3: 56 percent / lithium (hexamethylsilyl)amide / tetrahydrofuran / 4 h / -78 °C

4: 98 percent / HgCl₂, aq. CaCO₃ / acetonitrile / 1.5 h / 25 °C

5: 1.0 N HCl / tetrahydrofuran / 2 h / 0 °C

6: pyridine / diethyl ether; tetrahydrofuran / 1 h / 0 °C

With pyridine; hydrogenchloride; sodium hydroxide; silver nitrate; calcium carbonate; mercury dichloride; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; acetonitrile;

DOI:10.1021/ja00541a054

Reference yield:

(2R,3S)-3-[(6E,8E)-(1R,2S)-10-[3-(Acetyl-methyl-amino)-4-chloro-5-methoxy-phenyl]-2-(1-ethoxy-ethoxy)-4,4-bis-ethylsulfanyl-5-methoxy-1,9-dimethyl-deca-6,8-dienyl]-2-methyl-oxirane-2-carboxylic acid → Carbonic acid (14E,16E)-(6R,8S,9R,10S)-22-chloro-13,21-dimethoxy-2,6,9,17-tetramethyl-3,5,12-trioxo-7-oxa-2-aza-tricyclo[17.3.1.06,8]tricosa-1(23),14,16,19,21-pentaen-10-yl ester phenyl ester (75448-81-6,75494-71-2)

Guidance literature:

Multi-step reaction with 5 steps

1: diethyl ether / 0 °C

2: 56 percent / lithium (hexamethylsilyl)amide / tetrahydrofuran / 4 h / -78 °C

3: 98 percent / HgCl₂, aq. CaCO₃ / acetonitrile / 1.5 h / 25 °C

4: 1.0 N HCl / tetrahydrofuran / 2 h / 0 °C

5: pyridine / diethyl ether; tetrahydrofuran / 1 h / 0 °C

With pyridine; hydrogenchloride; calcium carbonate; mercury dichloride; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; acetonitrile;

DOI:10.1021/ja00541a054

upstream raw materials:

(14E,16E)-(6R,8S,9R,10S)-22-Chloro-10-hydroxy-13,21-dimethoxy-2,6,9,17-tetramethyl-7-oxa-2-aza-tricyclo[17.3.1.0^6,8]tricosa-1⁽²³⁾,14,16,19,21-pentaene-3,5,12-trione

phenyl chloroformate

(14E,16E)-(6R,8S,9R,10S)-22-Chloro-10-(1-ethoxy-ethoxy)-13,21-dimethoxy-2,6,9,17-tetramethyl-7-oxa-2-aza-tricyclo[17.3.1.0^6,8]tricosa-1⁽²³⁾,14,16,19,21-pentaene-3,5,12-trione

N-{2-Chloro-5-[(2E,4E)-(9R,10S)-9-(1-ethoxy-ethoxy)-7,7-bis-ethylsulfanyl-10-((2R,3S)-3-formyl-3-methyl-oxiranyl)-6-methoxy-2-methyl-undeca-2,4-dienyl]-3-methoxy-phenyl}-N-methyl-acetamide

Downstream raw materials:

(+/-)-maytansinol