3-tert-butoxycarbonylamino-2-hydroxy-3-phenyl-propionic acid 14,20-dihydroxy-10-methoxy-7,13,15,17,19,21-hexamethyl-22-(1-methyl-penta-2,4-dienyl)-2-oxo-oxacyclodocosa-3,5,11,16-tetraen-8-yl ester

Base Information

• Chemical Name: 3-tert-butoxycarbonylamino-2-hydroxy-3-phenyl-propionic acid 14,20-dihydroxy-10-methoxy-7,13,15,17,19,21-hexamethyl-22-(1-methyl-penta-2,4-dienyl)-2-oxo-oxacyclodocosa-3,5,11,16-tetraen-8-yl ester
• CAS No.: 1207166-45-7
• Molecular Formula: C₄₈H₇₁NO₁₀
• Molecular Weight: 822.092
• Mol file: 1207166-45-7.mol

Synonyms:3-tert-butoxycarbonylamino-2-hydroxy-3-phenyl-propionic acid 14,20-dihydroxy-10-methoxy-7,13,15,17,19,21-hexamethyl-22-(1-methyl-penta-2,4-dienyl)-2-oxo-oxacyclodocosa-3,5,11,16-tetraen-8-yl ester

Chemical Property of 3-tert-butoxycarbonylamino-2-hydroxy-3-phenyl-propionic acid 14,20-dihydroxy-10-methoxy-7,13,15,17,19,21-hexamethyl-22-(1-methyl-penta-2,4-dienyl)-2-oxo-oxacyclodocosa-3,5,11,16-tetraen-8-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-tert-butoxycarbonylamino-2-hydroxy-3-phenyl-propionic acid 14,20-dihydroxy-10-methoxy-7,13,15,17,19,21-hexamethyl-22-(1-methyl-penta-2,4-dienyl)-2-oxo-oxacyclodocosa-3,5,11,16-tetraen-8-yl ester

There total 10 articles about 3-tert-butoxycarbonylamino-2-hydroxy-3-phenyl-propionic acid 14,20-dihydroxy-10-methoxy-7,13,15,17,19,21-hexamethyl-22-(1-methyl-penta-2,4-dienyl)-2-oxo-oxacyclodocosa-3,5,11,16-tetraen-8-yl 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: 100.0%

3-tert-butoxycarbonylamino-3-phenyl-2-triethylsilanyloxy-propionic acid 14,20-bis(tert-butyl-dimethyl-silanyloxy)-10-methoxy-7,13,15,17,19,21-hexamethyl-22-(1-methyl-penta-2,4-dienyl)-2-oxo-oxacyclodocosa-3,5,11,16-tetraen-8-yl ester (1207166-55-9) → 3-tert-butoxycarbonylamino-2-hydroxy-3-phenyl-propionic acid 14,20-dihydroxy-10-methoxy-7,13,15,17,19,21-hexamethyl-22-(1-methyl-penta-2,4-dienyl)-2-oxo-oxacyclodocosa-3,5,11,16-tetraen-8-yl ester (1207166-45-7)

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; pyridine; at 20 ℃; for 96h;

DOI:10.1039/b921237j

Reference yield:

C45H83IO5Si2 (1082395-55-8) → 3-tert-butoxycarbonylamino-2-hydroxy-3-phenyl-propionic acid 14,20-dihydroxy-10-methoxy-7,13,15,17,19,21-hexamethyl-22-(1-methyl-penta-2,4-dienyl)-2-oxo-oxacyclodocosa-3,5,11,16-tetraen-8-yl ester (1207166-45-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: copper(I) thiophene-2-carboxylate / 1-methyl-pyrrolidin-2-one / 16 h / 20 °C

2.1: methanol; potassium fluoride / tetrahydrofuran / 2 h / 20 °C

3.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 20 °C

3.2: 0.33 h / 20 °C

4.1: pyridinium p-toluenesulfonate / methanol; dichloromethane / 0 - 20 °C

5.1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 1.17 h / 20 °C

6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.17 h / -78 °C

6.2: -78 - 0 °C

7.1: pyridine hydrogenfluoride / tetrahydrofuran; pyridine / 0 - 20 °C

With methanol; potassium fluoride; copper(I) thiophene-2-carboxylate; 2,4,6-trichlorobenzoyl chloride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; pyridine hydrogenfluoride; triethylamine; In tetrahydrofuran; pyridine; 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; toluene; 1.1: Stille-Liebeskind cross coupling / 3.1: Yamaguchi macrolactonization / 3.2: Yamaguchi macrolactonization;

DOI:10.1002/asia.201000541

Reference yield:

(5Z,13Z)-(2R,3R,4S,8S,9R,10R,11S,12S)-3,9-bis(tertbutyldimethylsilanyloxy)-11-hydroxy-2,4,6,8,10,12-hexamethylhexadeca-5,13,15-trienal (373645-86-4) → 3-tert-butoxycarbonylamino-2-hydroxy-3-phenyl-propionic acid 14,20-dihydroxy-10-methoxy-7,13,15,17,19,21-hexamethyl-22-(1-methyl-penta-2,4-dienyl)-2-oxo-oxacyclodocosa-3,5,11,16-tetraen-8-yl ester (1207166-45-7)

Guidance literature:

Multi-step reaction with 11 steps

1.1: N,N,N,N,N,N-hexamethylphosphoric triamide; 18-crown-6 ether; potassium carbonate / toluene / 421 h / 0 °C

2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2.5 h / 0 °C / pH 7 / aq. buffer

3.1: borane-THF; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / toluene / 4 h / -30 °C

4.1: pyridinium p-toluenesulfonate / dichloromethane / 0 - 20 °C

5.1: copper(I) thiophene-2-carboxylate / 1-methyl-pyrrolidin-2-one / 16 h / 20 °C

6.1: methanol; potassium fluoride / tetrahydrofuran / 2 h / 20 °C

7.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 20 °C

7.2: 0.33 h / 20 °C

8.1: pyridinium p-toluenesulfonate / methanol; dichloromethane / 0 - 20 °C

9.1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 1.17 h / 20 °C

10.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.17 h / -78 °C

10.2: -78 - 0 °C

11.1: pyridine hydrogenfluoride / tetrahydrofuran; pyridine / 0 - 20 °C

With methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium fluoride; borane-THF; copper(I) thiophene-2-carboxylate; 18-crown-6 ether; 2,4,6-trichlorobenzoyl chloride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; potassium carbonate; pyridine hydrogenfluoride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; pyridine; 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; toluene; 1.1: Still-Gennari olefination / 5.1: Stille-Liebeskind cross coupling / 7.1: Yamaguchi macrolactonization / 7.2: Yamaguchi macrolactonization;

DOI:10.1002/asia.201000541

upstream raw materials:

3-tert-butoxycarbonylamino-3-phenyl-2-triethylsilanyloxy-propionic acid 14,20-bis(tert-butyl-dimethyl-silanyloxy)-10-methoxy-7,13,15,17,19,21-hexamethyl-22-(1-methyl-penta-2,4-dienyl)-2-oxo-oxacyclodocosa-3,5,11,16-tetraen-8-yl ester

14,20-bis(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-10-methoxy-7,13,15,17,19,21-hexamethyl-22-(1-methyl-penta-2,4-dienyl)-oxacyclodocosa-3,5,11,16-tetraen-2-one

C₅₇H₁₀₈O₆Si₄

C₄₈H₈₄O₆Si₂