(3E,5E,10E,13E,15E)-(7S,8S,19S)-8-(1-Ethoxy-ethoxy)-1-(4-methoxy-benzyl)-7,11,13,19-tetramethyl-azacycloicosa-3,5,10,13,15-pentaen-2-one

Base Information

• Chemical Name: (3E,5E,10E,13E,15E)-(7S,8S,19S)-8-(1-Ethoxy-ethoxy)-1-(4-methoxy-benzyl)-7,11,13,19-tetramethyl-azacycloicosa-3,5,10,13,15-pentaen-2-one
• CAS No.: 213194-92-4
• Molecular Formula: C₃₅H₅₁NO₄
• Molecular Weight: 549.794
• Mol file: 213194-92-4.mol

Synonyms:

Chemical Property of (3E,5E,10E,13E,15E)-(7S,8S,19S)-8-(1-Ethoxy-ethoxy)-1-(4-methoxy-benzyl)-7,11,13,19-tetramethyl-azacycloicosa-3,5,10,13,15-pentaen-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3E,5E,10E,13E,15E)-(7S,8S,19S)-8-(1-Ethoxy-ethoxy)-1-(4-methoxy-benzyl)-7,11,13,19-tetramethyl-azacycloicosa-3,5,10,13,15-pentaen-2-one

There total 23 articles about (3E,5E,10E,13E,15E)-(7S,8S,19S)-8-(1-Ethoxy-ethoxy)-1-(4-methoxy-benzyl)-7,11,13,19-tetramethyl-azacycloicosa-3,5,10,13,15-pentaen-2-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:

(E)-4-methylhept-3-en-6-yn-1-ol (13857-47-1) → (3E,5E,10E,13E,15E)-(7S,8S,19S)-8-(1-Ethoxy-ethoxy)-1-(4-methoxy-benzyl)-7,11,13,19-tetramethyl-azacycloicosa-3,5,10,13,15-pentaen-2-one (213194-92-4)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 99 percent / dimethylformamide

2.1: 88 percent / I₂ / Cp₂ZrCl₂ / CH₂Cl₂

3.1: 99 percent / TBAF / tetrahydrofuran

4.1: tetrahydrofuran

4.2: 52 percent / NaOEt / Pd(PPh₃)4 / ethanol; benzene / Heating

5.1: Dess-Martin reagent / CH₂Cl₂

6.1: 58 percent / Buⁿ2BOTf; Et₃N / CH₂Cl₂

7.1: 85 percent / PPTS

8.1: 72 percent / LiBH₄ / methanol; tetrahydrofuran

9.1: Dess-Martin reagent / CH₂Cl₂

10.1: 67 percent / LiN(TMS)2 / tetrahydrofuran

11.1: tetra-n-butylammonium fluoride / tetrahydrofuran

12.1: (EtO)2POCN; Et₃N / dimethylformamide

With lithium borohydride; diethyl cyanophosphonate; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; iodine; pyridinium p-toluenesulfonate; Dess-Martin periodane; triethylamine; lithium hexamethyldisilazane; zirconocene dichloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Etherification / 2.1: Addition / 3.1: Hydrolysis / 4.1: Addition / 4.2: Addition / 5.1: Dess-Martin oxidation / 6.1: Evans aldol reaction / 7.1: Etherification / 8.1: Reduction / 9.1: Oxidation / 10.1: Wittig-Horner reaction / 11.1: Decomposition / 12.1: Cyclization;

DOI:10.7164/antibiotics.51.688

Reference yield:

(E)-7-acetoxy-4-methylhept-4-en-1-yne (13927-59-8) → (3E,5E,10E,13E,15E)-(7S,8S,19S)-8-(1-Ethoxy-ethoxy)-1-(4-methoxy-benzyl)-7,11,13,19-tetramethyl-azacycloicosa-3,5,10,13,15-pentaen-2-one (213194-92-4)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 98 percent / KCN / ethanol

2.1: 99 percent / dimethylformamide

3.1: 88 percent / I₂ / Cp₂ZrCl₂ / CH₂Cl₂

4.1: 99 percent / TBAF / tetrahydrofuran

5.1: tetrahydrofuran

5.2: 52 percent / NaOEt / Pd(PPh₃)4 / ethanol; benzene / Heating

6.1: Dess-Martin reagent / CH₂Cl₂

7.1: 58 percent / Buⁿ2BOTf; Et₃N / CH₂Cl₂

8.1: 85 percent / PPTS

9.1: 72 percent / LiBH₄ / methanol; tetrahydrofuran

10.1: Dess-Martin reagent / CH₂Cl₂

11.1: 67 percent / LiN(TMS)2 / tetrahydrofuran

12.1: tetra-n-butylammonium fluoride / tetrahydrofuran

13.1: (EtO)2POCN; Et₃N / dimethylformamide

With potassium cyanide; lithium borohydride; diethyl cyanophosphonate; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; iodine; pyridinium p-toluenesulfonate; Dess-Martin periodane; triethylamine; lithium hexamethyldisilazane; zirconocene dichloride; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Deacetylation / 2.1: Etherification / 3.1: Addition / 4.1: Hydrolysis / 5.1: Addition / 5.2: Addition / 6.1: Dess-Martin oxidation / 7.1: Evans aldol reaction / 8.1: Etherification / 9.1: Reduction / 10.1: Oxidation / 11.1: Wittig-Horner reaction / 12.1: Decomposition / 13.1: Cyclization;

DOI:10.7164/antibiotics.51.688

Reference yield:

2-cyclopropylpent-4-yn-2-ol (6712-34-1) → (3E,5E,10E,13E,15E)-(7S,8S,19S)-8-(1-Ethoxy-ethoxy)-1-(4-methoxy-benzyl)-7,11,13,19-tetramethyl-azacycloicosa-3,5,10,13,15-pentaen-2-one (213194-92-4)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 47 percent HBr

2.1: 79 percent / dimethylformamide

3.1: 98 percent / KCN / ethanol

4.1: 99 percent / dimethylformamide

5.1: 88 percent / I₂ / Cp₂ZrCl₂ / CH₂Cl₂

6.1: 99 percent / TBAF / tetrahydrofuran

7.1: tetrahydrofuran

7.2: 52 percent / NaOEt / Pd(PPh₃)4 / ethanol; benzene / Heating

8.1: Dess-Martin reagent / CH₂Cl₂

9.1: 58 percent / Buⁿ2BOTf; Et₃N / CH₂Cl₂

10.1: 85 percent / PPTS

11.1: 72 percent / LiBH₄ / methanol; tetrahydrofuran

12.1: Dess-Martin reagent / CH₂Cl₂

13.1: 67 percent / LiN(TMS)2 / tetrahydrofuran

14.1: tetra-n-butylammonium fluoride / tetrahydrofuran

15.1: (EtO)2POCN; Et₃N / dimethylformamide

With potassium cyanide; lithium borohydride; diethyl cyanophosphonate; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen bromide; iodine; pyridinium p-toluenesulfonate; Dess-Martin periodane; triethylamine; lithium hexamethyldisilazane; zirconocene dichloride; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Addition / 2.1: Acylation / 3.1: Deacetylation / 4.1: Etherification / 5.1: Addition / 6.1: Hydrolysis / 7.1: Addition / 7.2: Addition / 8.1: Dess-Martin oxidation / 9.1: Evans aldol reaction / 10.1: Etherification / 11.1: Reduction / 12.1: Oxidation / 13.1: Wittig-Horner reaction / 14.1: Decomposition / 15.1: Cyclization;

DOI:10.7164/antibiotics.51.688

upstream raw materials:

(2E,4E,9E,12E,14E)-(6S,7S,18S)-7-(1-Ethoxy-ethoxy)-19-(4-methoxy-benzylamino)-6,10,12,18-tetramethyl-nonadeca-2,4,9,12,14-pentaenoic acid

(S)-3,7-dimethyl-6-octen-1-ol

(E)-4-methylhept-3-en-6-yn-1-ol

(E)-7-acetoxy-4-methylhept-4-en-1-yne