1-[3-(3-tert-butoxycarbonyloxy-phenyl)-2-(2-{[3-(6-hydroxy-8-iodo-7-methyl-octa-1,3,7-trienyl)-1,4-dimethyl-2,9-dioxa-bicyclo[3.3.1]nonane-6-carbonyl]-amino}-3-methyl-butyrylamino)-propionyl]-hexahydro-pyridazine-3-carboxylic acid

Base Information

• Chemical Name: 1-[3-(3-tert-butoxycarbonyloxy-phenyl)-2-(2-{[3-(6-hydroxy-8-iodo-7-methyl-octa-1,3,7-trienyl)-1,4-dimethyl-2,9-dioxa-bicyclo[3.3.1]nonane-6-carbonyl]-amino}-3-methyl-butyrylamino)-propionyl]-hexahydro-pyridazine-3-carboxylic acid
• CAS No.: 382139-23-3
• Molecular Formula: C₄₃H₆₁IN₄O₁₁
• Molecular Weight: 936.882
• Mol file: 382139-23-3.mol

Synonyms:1-[3-(3-tert-butoxycarbonyloxy-phenyl)-2-(2-{[3-(6-hydroxy-8-iodo-7-methyl-octa-1,3,7-trienyl)-1,4-dimethyl-2,9-dioxa-bicyclo[3.3.1]nonane-6-carbonyl]-amino}-3-methyl-butyrylamino)-propionyl]-hexahydro-pyridazine-3-carboxylic acid

Chemical Property of 1-[3-(3-tert-butoxycarbonyloxy-phenyl)-2-(2-{[3-(6-hydroxy-8-iodo-7-methyl-octa-1,3,7-trienyl)-1,4-dimethyl-2,9-dioxa-bicyclo[3.3.1]nonane-6-carbonyl]-amino}-3-methyl-butyrylamino)-propionyl]-hexahydro-pyridazine-3-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[3-(3-tert-butoxycarbonyloxy-phenyl)-2-(2-{[3-(6-hydroxy-8-iodo-7-methyl-octa-1,3,7-trienyl)-1,4-dimethyl-2,9-dioxa-bicyclo[3.3.1]nonane-6-carbonyl]-amino}-3-methyl-butyrylamino)-propionyl]-hexahydro-pyridazine-3-carboxylic acid

There total 22 articles about 1-[3-(3-tert-butoxycarbonyloxy-phenyl)-2-(2-{[3-(6-hydroxy-8-iodo-7-methyl-octa-1,3,7-trienyl)-1,4-dimethyl-2,9-dioxa-bicyclo[3.3.1]nonane-6-carbonyl]-amino}-3-methyl-butyrylamino)-propionyl]-hexahydro-pyridazine-3-carboxylic acid 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: 100.0%

1-[3-(3-tert-butoxycarbonyloxy-phenyl)-2-(2-{[3-(6-hydroxy-8-iodo-7-methyl-octa-1,3,7-trienyl)-1,4-dimethyl-2,9-dioxa-bicyclo[3.3.1]nonane-6-carbonyl]-amino}-3-methyl-butyrylamino)-propionyl]-hexahydro-pyridazine-3-carboxylic acid methyl ester (382139-08-4) → 1-[3-(3-tert-butoxycarbonyloxy-phenyl)-2-(2-{[3-(6-hydroxy-8-iodo-7-methyl-octa-1,3,7-trienyl)-1,4-dimethyl-2,9-dioxa-bicyclo[3.3.1]nonane-6-carbonyl]-amino}-3-methyl-butyrylamino)-propionyl]-hexahydro-pyridazine-3-carboxylic acid (382139-23-3)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 1h;

DOI:10.1002/1521-3773(20011001)40:19<3632::AID-ANIE3632>3.0.CO;2-5

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 1-[3-(3-tert-butoxycarbonyloxy-phenyl)-2-(2-{[3-(6-hydroxy-8-iodo-7-methyl-octa-1,3,7-trienyl)-1,4-dimethyl-2,9-dioxa-bicyclo[3.3.1]nonane-6-carbonyl]-amino}-3-methyl-butyrylamino)-propionyl]-hexahydro-pyridazine-3-carboxylic acid (382139-23-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / triethylamine; DMAP / CH₂Cl₂ / 2.5 h

2: H₂ / Pd/C / ethanol / 3 h / 2585.81 Torr

3: 385 mg / triethylamine; HBTU / acetonitrile / 1.5 h / 20 °C

4: H₂ / Pd/C / ethanol / 4 h / 2585.81 Torr

5: 63 mg / triethylamine; HATU / acetonitrile / 3 h / 20 °C

6: lithium hydroxide monohydrate / tetrahydrofuran; H₂O / 1 h / 0 °C

With dmap; lithium hydroxide; hydrogen; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; acetonitrile;

DOI:10.1021/ja020091v

Reference yield:

(S)-1-[(S)-2-Benzyloxycarbonylamino-3-(3-hydroxy-phenyl)-propionyl]-hexahydro-pyridazine-3-carboxylic acid methyl ester (382139-04-0) → 1-[3-(3-tert-butoxycarbonyloxy-phenyl)-2-(2-{[3-(6-hydroxy-8-iodo-7-methyl-octa-1,3,7-trienyl)-1,4-dimethyl-2,9-dioxa-bicyclo[3.3.1]nonane-6-carbonyl]-amino}-3-methyl-butyrylamino)-propionyl]-hexahydro-pyridazine-3-carboxylic acid (382139-23-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / triethylamine; DMAP / CH₂Cl₂ / 2.5 h

2: H₂ / Pd/C / ethanol / 3 h / 2585.81 Torr

3: 385 mg / triethylamine; HBTU / acetonitrile / 1.5 h / 20 °C

4: H₂ / Pd/C / ethanol / 4 h / 2585.81 Torr

5: 63 mg / triethylamine; HATU / acetonitrile / 3 h / 20 °C

6: lithium hydroxide monohydrate / tetrahydrofuran; H₂O / 1 h / 0 °C

With dmap; lithium hydroxide; hydrogen; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; acetonitrile;

DOI:10.1021/ja020091v

upstream raw materials:

1-[3-(3-tert-butoxycarbonyloxy-phenyl)-2-(2-{[3-(6-hydroxy-8-iodo-7-methyl-octa-1,3,7-trienyl)-1,4-dimethyl-2,9-dioxa-bicyclo[3.3.1]nonane-6-carbonyl]-amino}-3-methyl-butyrylamino)-propionyl]-hexahydro-pyridazine-3-carboxylic acid methyl ester

di-tert-butyl dicarbonate

(4S)-4-benzyl-3-(hex-5-enoyl)-1,3-oxazolidin-2-one

1-(4(S)-Benzyl-2-oxo-oxazolidin-3-yl)-hexane-1,5-dione

Downstream raw materials:

C₆₀H₈₉N₅O₁₂

C₃₈H₅₁IN₄O₈

(-)-sanglifehrin A

C₄₃H₅₉IN₄O₁₀