(1R,4S,7S,10S,14S)-4-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-propyl]-10-((1R,4S)-4-methoxy-1-methyl-heptyl)-1,3,7,11,11,14-hexamethyl-9-oxa-16-thia-3,6,13,18-tetraaza-bicyclo[13.2.1]octadec-15⁽¹⁸⁾-ene-2,5,8,12-tetraone

Base Information

• Chemical Name: (1R,4S,7S,10S,14S)-4-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-propyl]-10-((1R,4S)-4-methoxy-1-methyl-heptyl)-1,3,7,11,11,14-hexamethyl-9-oxa-16-thia-3,6,13,18-tetraaza-bicyclo[13.2.1]octadec-15⁽¹⁸⁾-ene-2,5,8,12-tetraone
• CAS No.: 866555-22-8
• Molecular Formula: C₄₇H₇₂N₄O₇SSi
• Molecular Weight: 865.263

Synonyms:(1R,4S,7S,10S,14S)-4-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-propyl]-10-((1R,4S)-4-methoxy-1-methyl-heptyl)-1,3,7,11,11,14-hexamethyl-9-oxa-16-thia-3,6,13,18-tetraaza-bicyclo[13.2.1]octadec-15⁽¹⁸⁾-ene-2,5,8,12-tetraone

Chemical Property of (1R,4S,7S,10S,14S)-4-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-propyl]-10-((1R,4S)-4-methoxy-1-methyl-heptyl)-1,3,7,11,11,14-hexamethyl-9-oxa-16-thia-3,6,13,18-tetraaza-bicyclo[13.2.1]octadec-15⁽¹⁸⁾-ene-2,5,8,12-tetraone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (1R,4S,7S,10S,14S)-4-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-propyl]-10-((1R,4S)-4-methoxy-1-methyl-heptyl)-1,3,7,11,11,14-hexamethyl-9-oxa-16-thia-3,6,13,18-tetraaza-bicyclo[13.2.1]octadec-15⁽¹⁸⁾-ene-2,5,8,12-tetraone

There total 29 articles about (1R,4S,7S,10S,14S)-4-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-propyl]-10-((1R,4S)-4-methoxy-1-methyl-heptyl)-1,3,7,11,11,14-hexamethyl-9-oxa-16-thia-3,6,13,18-tetraaza-bicyclo[13.2.1]octadec-15⁽¹⁸⁾-ene-2,5,8,12-tetraone 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: 31.0%

(2S,3S)-2-[((R)-2-{(S)-1-[(3S,4R,7S)-3-((S)-2-Amino-propionyloxy)-7-methoxy-2,2,4-trimethyl-decanoylamino]-ethyl}-4-methyl-4,5-dihydro-thiazole-4-carbonyl)-methyl-amino]-5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-pentanoic acid (866555-21-7) → (1R,4R,7S,10S,14S)-4-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-propyl]-10-((1R,4S)-4-methoxy-1-methyl-heptyl)-1,3,7,11,11,14-hexamethyl-9-oxa-16-thia-3,6,13,18-tetraaza-bicyclo[13.2.1]octadec-15(18)-ene-2,5,8,12-tetraone (866555-24-0) + (1R,4S,7S,10S,14S)-4-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-propyl]-10-((1R,4S)-4-methoxy-1-methyl-heptyl)-1,3,7,11,11,14-hexamethyl-9-oxa-16-thia-3,6,13,18-tetraaza-bicyclo[13.2.1]octadec-15(18)-ene-2,5,8,12-tetraone (866555-22-8) + (1R,4S,7S,10S,14R)-4-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-propyl]-10-((1R,4S)-4-methoxy-1-methyl-heptyl)-1,3,7,11,11,14-hexamethyl-9-oxa-16-thia-3,6,13,18-tetraaza-bicyclo[13.2.1]octadec-15(18)-ene-2,5,8,12-tetraone (866555-23-9)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; potassium carbonate; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; at 25 ℃; for 24h;

DOI:10.1002/anie.200500702

Reference yield:

(2R,3R)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-oxirane-2-carboxylic acid (866555-26-2) → (1R,4S,7S,10S,14S)-4-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-propyl]-10-((1R,4S)-4-methoxy-1-methyl-heptyl)-1,3,7,11,11,14-hexamethyl-9-oxa-16-thia-3,6,13,18-tetraaza-bicyclo[13.2.1]octadec-15(18)-ene-2,5,8,12-tetraone (866555-22-8)

Guidance literature:

Multi-step reaction with 18 steps

1.1: hexane / 40 h / 20 °C

2.1: K₂CO₃ / acetone / 18 h / 20 °C

3.1: pyridine / CH₂Cl₂ / 0.42 h / 0 °C

4.1: NaN₃ / dimethylformamide / 0.67 h / 20 °C

5.1: H₂ / Pd/C / methanol / 1 h / 20 °C / 760 Torr

6.1: 1.46 g / 1-hydroxy-7-azabenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; iPr₂NEt / CH₂Cl₂ / 18 h / 20 °C

7.1: 85 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

8.1: 83 percent / NaH / tetrahydrofuran / 0.5 h / 0 °C

9.1: 100 percent / aq. HCl / tetrahydrofuran / 2 h / 20 °C

10.1: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 0.5 h / 20 °C

10.2: 88 percent / CH₂Cl₂ / 24 h / 20 °C

11.1: 79 percent / PMe₃ / toluene / 0.03 h / 0 °C

12.1: H₂ / Pd(OH)2/C / ethanol / 3 h / 20 °C / 760 Torr

13.1: H₂S; Et₃N / methanol / 73 h / 20 °C

14.1: 87.1 mg / (7-azabenzotriazol-1-yloxy)tripyrrolidinophosphonium*PF₆; iPr₂NEt / dimethylformamide / 18 h / 20 °C

15.1: 78.8 percent / diethylaminosulfur trifluoride / CH₂Cl₂ / 2 h / -78 °C

16.1: Me₃SnOH / 1,2-dichloro-ethane / 48 h / 90 °C

17.1: PMe₃; water / tetrahydrofuran; toluene / 2 h / 0 °C

18.1: 4.6 mg / O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium*PF₆; 1-hydroxy-7-azabenzotriazole; K₂CO₃ / CH₂Cl₂ / 24 h / 20 °C

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; sodium azide; 1-hydroxy-7-aza-benzotriazole; diethylamino-sulfur trifluoride; hydrogen sulfide; water; hydrogen; sodium hydride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; ((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V); trimethyltin(IV) hydroxide; trimethylphosphane; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; toluene; 17.1: Staudinger reduction;

DOI:10.1021/ja060064v

Reference yield:

(2R,3S)-5-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-3-methyl-pentanoic acid methyl ester (866555-10-4) → (1R,4S,7S,10S,14S)-4-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-propyl]-10-((1R,4S)-4-methoxy-1-methyl-heptyl)-1,3,7,11,11,14-hexamethyl-9-oxa-16-thia-3,6,13,18-tetraaza-bicyclo[13.2.1]octadec-15(18)-ene-2,5,8,12-tetraone (866555-22-8)

Guidance literature:

Multi-step reaction with 16 steps

1.1: pyridine / CH₂Cl₂ / 0.42 h / 0 °C

2.1: NaN₃ / dimethylformamide / 0.67 h / 20 °C

3.1: H₂ / Pd/C / methanol / 1 h / 20 °C / 760 Torr

4.1: 1.46 g / 1-hydroxy-7-azabenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; iPr₂NEt / CH₂Cl₂ / 18 h / 20 °C

5.1: 85 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

6.1: 83 percent / NaH / tetrahydrofuran / 0.5 h / 0 °C

7.1: 100 percent / aq. HCl / tetrahydrofuran / 2 h / 20 °C

8.1: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 0.5 h / 20 °C

8.2: 88 percent / CH₂Cl₂ / 24 h / 20 °C

9.1: 79 percent / PMe₃ / toluene / 0.03 h / 0 °C

10.1: H₂ / Pd(OH)2/C / ethanol / 3 h / 20 °C / 760 Torr

11.1: H₂S; Et₃N / methanol / 73 h / 20 °C

12.1: 87.1 mg / (7-azabenzotriazol-1-yloxy)tripyrrolidinophosphonium*PF₆; iPr₂NEt / dimethylformamide / 18 h / 20 °C

13.1: 78.8 percent / diethylaminosulfur trifluoride / CH₂Cl₂ / 2 h / -78 °C

14.1: Me₃SnOH / 1,2-dichloro-ethane / 48 h / 90 °C

15.1: PMe₃; water / tetrahydrofuran; toluene / 2 h / 0 °C

16.1: 4.6 mg / O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium*PF₆; 1-hydroxy-7-azabenzotriazole; K₂CO₃ / CH₂Cl₂ / 24 h / 20 °C

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; sodium azide; 1-hydroxy-7-aza-benzotriazole; diethylamino-sulfur trifluoride; hydrogen sulfide; water; hydrogen; sodium hydride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; ((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V); trimethyltin(IV) hydroxide; trimethylphosphane; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; 15.1: Staudinger reduction;

DOI:10.1021/ja060064v

upstream raw materials:

(2S,3S)-2-[((R)-2-{(S)-1-[(3S,4R,7S)-3-((S)-2-Amino-propionyloxy)-7-methoxy-2,2,4-trimethyl-decanoylamino]-ethyl}-4-methyl-4,5-dihydro-thiazole-4-carbonyl)-methyl-amino]-5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-pentanoic acid

5-methoxy-2-methyloctanal

(2R,5S)-5-Methoxy-2-methyl-octan-1-ol

(3S,4R)-3-hydroxy-7-methoxy-2,2,4-trimethyldecanoic acid methyl ester

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