(3E,8Z,10E)-(6R,7S,13R,15R)-7-(4-Methoxy-benzyloxy)-13,15-bis-methoxymethoxy-6-methyl-17-oxo-1-phenylselanyl-cycloheptadeca-3,8,10-trienecarboxylic acid methyl ester

Base Information

• Chemical Name: (3E,8Z,10E)-(6R,7S,13R,15R)-7-(4-Methoxy-benzyloxy)-13,15-bis-methoxymethoxy-6-methyl-17-oxo-1-phenylselanyl-cycloheptadeca-3,8,10-trienecarboxylic acid methyl ester
• CAS No.: 773104-89-5
• Molecular Formula: C₃₈H₅₀O₉Se
• Molecular Weight: 729.77

Synonyms:(3E,8Z,10E)-(6R,7S,13R,15R)-7-(4-Methoxy-benzyloxy)-13,15-bis-methoxymethoxy-6-methyl-17-oxo-1-phenylselanyl-cycloheptadeca-3,8,10-trienecarboxylic acid methyl ester

Chemical Property of (3E,8Z,10E)-(6R,7S,13R,15R)-7-(4-Methoxy-benzyloxy)-13,15-bis-methoxymethoxy-6-methyl-17-oxo-1-phenylselanyl-cycloheptadeca-3,8,10-trienecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3E,8Z,10E)-(6R,7S,13R,15R)-7-(4-Methoxy-benzyloxy)-13,15-bis-methoxymethoxy-6-methyl-17-oxo-1-phenylselanyl-cycloheptadeca-3,8,10-trienecarboxylic acid methyl ester

There total 17 articles about (3E,8Z,10E)-(6R,7S,13R,15R)-7-(4-Methoxy-benzyloxy)-13,15-bis-methoxymethoxy-6-methyl-17-oxo-1-phenylselanyl-cycloheptadeca-3,8,10-trienecarboxylic acid methyl 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:

Phenylselenyl chloride (5707-04-0) + (2RS,4E,7R,8S,9Z,11E,14R,16R)-2-methoxycarbonyl-14,16-di(methoxymethoxy)-8-[(4-methoxyphenyl)methoxy]-7-methyl-4,9,11-cycloheptadecatrien-1-one (773104-88-4) → (3E,8Z,10E)-(6R,7S,13R,15R)-7-(4-Methoxy-benzyloxy)-13,15-bis-methoxymethoxy-6-methyl-17-oxo-1-phenylselanyl-cycloheptadeca-3,8,10-trienecarboxylic acid methyl ester (773104-89-5)

Guidance literature:

(2RS,4E,7R,8S,9Z,11E,14R,16R)-2-methoxycarbonyl-14,16-di(methoxymethoxy)-8-[(4-methoxyphenyl)methoxy]-7-methyl-4,9,11-cycloheptadecatrien-1-one; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h;

Phenylselenyl chloride; In tetrahydrofuran; toluene; at -78 ℃; for 2h;

DOI:10.1021/ja048320w

Reference yield:

(2R)-1-cyano-2-hydroxy-4-pentyne (182681-88-5) → (3E,8Z,10E)-(6R,7S,13R,15R)-7-(4-Methoxy-benzyloxy)-13,15-bis-methoxymethoxy-6-methyl-17-oxo-1-phenylselanyl-cycloheptadeca-3,8,10-trienecarboxylic acid methyl ester (773104-89-5)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 5.62 g / imidazole / dimethylformamide / 13.5 h / 0 °C

2.1: 100 percent / DIBAL-H / toluene / 2 h / -52 °C

3.1: BF₃*Et₂O / CH₂Cl₂ / 0.75 h / -78 °C

4.1: Dess-Martin periodinane / CH₂Cl₂ / 6.5 h / 0 °C

5.1: 7.95 g / aq. HF / acetonitrile / 8 h / 20 °C

6.1: 100 percent / Et₂BOMe; NaBH₄ / tetrahydrofuran; methanol / 8 h / -78 °C

7.1: 93 percent / imidazole / dimethylformamide / 5 h / 0 °C

8.1: 97 percent / NBS; AgNO₃ / acetone / 0.5 h / 20 °C

9.1: Pd₂(dba)3; PPh₃; Bu₃SnH / tetrahydrofuran / 2 h

9.2: 84 percent / I₂ / CH₂Cl₂ / 1 h / 0 °C

10.1: 97 percent / CuCl; Pd(PPh₃)4 / dimethylsulfoxide; tetrahydrofuran / 2 h

11.1: 94 percent / NH₄F / methanol / 24 h / 0 °C

12.1: 100 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

13.1: 100 percent / HF*pyridine / 45 h / 0 °C

14.1: 94 percent / iPr₂NEt / CH₂Cl₂ / 41 h

15.1: 96 percent / toluene; methanol / 5 h / 110 °C

16.1: Pd(PPh₃)4; dppe / tetrahydrofuran / 3 h

17.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

17.2: 331 mg / tetrahydrofuran; toluene / 2 h / -78 °C

With pyridine; 1H-imidazole; ammonium fluoride; sodium tetrahydroborate; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; diethyl methoxy borane; boron trifluoride diethyl etherate; hydrogen fluoride; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; silver nitrate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 1,2-bis-(diphenylphosphino)ethane; copper(l) chloride; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 3.1: Mukaiyama aldol reaction / 4.1: Dess-Martin oxidation / 6.1: Prasad's procedure / 10.1: Stille coupling;

DOI:10.1021/ja048320w

Reference yield:

(3R)-3-{[tert-butyl(dimethyl)silyl]oxy}hex-5-ynal (640270-59-3) → (3E,8Z,10E)-(6R,7S,13R,15R)-7-(4-Methoxy-benzyloxy)-13,15-bis-methoxymethoxy-6-methyl-17-oxo-1-phenylselanyl-cycloheptadeca-3,8,10-trienecarboxylic acid methyl ester (773104-89-5)

Guidance literature:

Multi-step reaction with 15 steps

1.1: BF₃*Et₂O / CH₂Cl₂ / 0.75 h / -78 °C

2.1: Dess-Martin periodinane / CH₂Cl₂ / 6.5 h / 0 °C

3.1: 7.95 g / aq. HF / acetonitrile / 8 h / 20 °C

4.1: 100 percent / Et₂BOMe; NaBH₄ / tetrahydrofuran; methanol / 8 h / -78 °C

5.1: 93 percent / imidazole / dimethylformamide / 5 h / 0 °C

6.1: 97 percent / NBS; AgNO₃ / acetone / 0.5 h / 20 °C

7.1: Pd₂(dba)3; PPh₃; Bu₃SnH / tetrahydrofuran / 2 h

7.2: 84 percent / I₂ / CH₂Cl₂ / 1 h / 0 °C

8.1: 97 percent / CuCl; Pd(PPh₃)4 / dimethylsulfoxide; tetrahydrofuran / 2 h

9.1: 94 percent / NH₄F / methanol / 24 h / 0 °C

10.1: 100 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

11.1: 100 percent / HF*pyridine / 45 h / 0 °C

12.1: 94 percent / iPr₂NEt / CH₂Cl₂ / 41 h

13.1: 96 percent / toluene; methanol / 5 h / 110 °C

14.1: Pd(PPh₃)4; dppe / tetrahydrofuran / 3 h

15.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

15.2: 331 mg / tetrahydrofuran; toluene / 2 h / -78 °C

With pyridine; 1H-imidazole; ammonium fluoride; sodium tetrahydroborate; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; diethyl methoxy borane; boron trifluoride diethyl etherate; hydrogen fluoride; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; Dess-Martin periodane; pyridine hydrogenfluoride; silver nitrate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 1,2-bis-(diphenylphosphino)ethane; copper(l) chloride; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 1.1: Mukaiyama aldol reaction / 2.1: Dess-Martin oxidation / 4.1: Prasad's procedure / 8.1: Stille coupling;

DOI:10.1021/ja048320w

upstream raw materials:

Phenylselenyl chloride

(2RS,4E,7R,8S,9Z,11E,14R,16R)-2-methoxycarbonyl-14,16-di(methoxymethoxy)-8-[(4-methoxyphenyl)methoxy]-7-methyl-4,9,11-cycloheptadecatrien-1-one

(2R)-1-cyano-2-hydroxy-4-pentyne

(3R)-3-{[tert-butyl(dimethyl)silyl]oxy}hex-5-ynal

Downstream raw materials:

(Z)-(2R,3S,3aS,5aS,7R,9R,13aS,13bR)-3-(4-Methoxy-benzyloxy)-7,9-bis-methoxymethoxy-2-methyl-11-oxo-2,3,3a,5a,6,7,8,9,10,11,13a,13b-dodecahydro-1H-cyclodeca[e]indene-12-carboxylic acid methyl ester

(2Z,4E,7R,8S,9Z,11E,14R,16R)-2-methoxycarbonyl-14,16-di(methoxymethoxy)-8-[(4-methoxyphenyl)methoxy]-7-methyl-2,4,9,11-cycloheptadecatetraen-1-one

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