2-[(4aS,8R,8aR)-4a-Benzyl-8-{[(R)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-methyl}-octahydro-naphthalen-(2E)-ylidene]-4-methylsulfanyl-butyric acid methyl ester

Base Information

• Chemical Name: 2-[(4aS,8R,8aR)-4a-Benzyl-8-{[(R)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-methyl}-octahydro-naphthalen-(2E)-ylidene]-4-methylsulfanyl-butyric acid methyl ester
• CAS No.: 82938-77-0
• Molecular Formula: C₃₈H₅₂N₂O₆S
• Molecular Weight: 664.907

Synonyms:

Chemical Property of 2-[(4aS,8R,8aR)-4a-Benzyl-8-{[(R)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-methyl}-octahydro-naphthalen-(2E)-ylidene]-4-methylsulfanyl-butyric acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(4aS,8R,8aR)-4a-Benzyl-8-{[(R)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-methyl}-octahydro-naphthalen-(2E)-ylidene]-4-methylsulfanyl-butyric acid methyl ester

There total 43 articles about 2-[(4aS,8R,8aR)-4a-Benzyl-8-{[(R)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-methyl}-octahydro-naphthalen-(2E)-ylidene]-4-methylsulfanyl-butyric 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:

2-benzylcyclohexan-1-one (946-33-8) → 2-[(4aR,8S,8aS)-4a-Benzyl-8-{[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-methyl}-octahydro-naphthalen-(2Z)-ylidene]-4-methylsulfanyl-butyric acid methyl ester (82938-77-0)

Guidance literature:

Multi-step reaction with 12 steps

1: 49 percent / potassium hydroxide / diethyl ether; ethanol / 4 h / 0 °C

2: 77 percent / p-toluenesulfonic acid monohydrate / benzene / 18 h / Heating

3: 1.) diborane, 2.) sodium hydroxide, 30percent hydrogen peroxide / 1.) tetrahydrofuran, R_.T_. 3 h, 2.) 0 degC, methanol

4: Jones reagent / acetone

5: tetrahydrofuran / 1.) 10 min., 0 degC, 2.) reflux, 20 min.

6: 1.) borane, 2.) sodium hydroxide, 30percent hydrogen peroxide / 1.) THF, R_.T_. 1.5 h, methanol, 2.) 0 degC, 15 min., sodium sulfite

7: 95 percent / pyridine / 72 h / 0 °C

8: 28 percent / sodium azide / dimethylformamide / 1 h / 125 °C

9: 89 percent / 3N hydrochloric acid / methanol / 2.5 h / Ambient temperature

10: 96 percent / 1.) diisopropylamine, n-butyllithium / tetrahydrofuran; hexane / 1.) 0 degC, 15 min., 2.) -78 degC, 35 min.

11: H₂ / platinum oxide / methanol / 1 h / 1551.4 Torr

12: 39 percent / CH₂Cl₂ / Ambient temperature

With hydrogenchloride; potassium hydroxide; sodium hydroxide; n-butyllithium; sodium azide; jones reagent; borane; hydrogen; dihydrogen peroxide; toluene-4-sulfonic acid; diisopropylamine; diborane; platinum(IV) oxide; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1139/v82-151

Reference yield:

1,2,3,5,6,7,8,8a-octahydro-3-oxo-8a-phenylmethylnaphthalene (70043-58-2) → 2-[(4aS,8R,8aR)-4a-Benzyl-8-{[(R)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-methyl}-octahydro-naphthalen-(2Z)-ylidene]-4-methylsulfanyl-butyric acid methyl ester (82938-75-8,82938-76-9,82938-77-0,82938-78-1)

Guidance literature:

Multi-step reaction with 11 steps

1: 77 percent / p-toluenesulfonic acid monohydrate / benzene / 18 h / Heating

2: 1.) diborane, 2.) sodium hydroxide, 30percent hydrogen peroxide / 1.) tetrahydrofuran, R_.T_. 3 h, 2.) 0 degC, methanol

3: Jones reagent / acetone

4: tetrahydrofuran / 1.) 10 min., 0 degC, 2.) reflux, 20 min.

5: 1.) borane, 2.) sodium hydroxide, 30percent hydrogen peroxide / 1.) THF, R_.T_. 1.5 h, methanol, 2.) 0 degC, 15 min., sodium sulfite

6: 95 percent / pyridine / 72 h / 0 °C

7: 28 percent / sodium azide / dimethylformamide / 1 h / 125 °C

8: 89 percent / 3N hydrochloric acid / methanol / 2.5 h / Ambient temperature

9: 96 percent / 1.) diisopropylamine, n-butyllithium / tetrahydrofuran; hexane / 1.) 0 degC, 15 min., 2.) -78 degC, 35 min.

10: H₂ / platinum oxide / methanol / 1 h / 1551.4 Torr

11: 31 percent / CH₂Cl₂ / Ambient temperature

With hydrogenchloride; sodium hydroxide; n-butyllithium; sodium azide; jones reagent; borane; hydrogen; dihydrogen peroxide; toluene-4-sulfonic acid; diisopropylamine; diborane; platinum(IV) oxide; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1139/v82-151

Reference yield:

1,2,3,5,6,7,8,8a-octahydro-3-oxo-8a-phenylmethylnaphthalene (70043-58-2) → 2-[(4aS,8R,8aR)-4a-Benzyl-8-{[(R)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-methyl}-octahydro-naphthalen-(2E)-ylidene]-4-methylsulfanyl-butyric acid methyl ester (82938-75-8,82938-76-9,82938-77-0,82938-78-1)

Guidance literature:

Multi-step reaction with 11 steps

1: 77 percent / p-toluenesulfonic acid monohydrate / benzene / 18 h / Heating

2: 1.) diborane, 2.) sodium hydroxide, 30percent hydrogen peroxide / 1.) tetrahydrofuran, R_.T_. 3 h, 2.) 0 degC, methanol

3: Jones reagent / acetone

4: tetrahydrofuran / 1.) 10 min., 0 degC, 2.) reflux, 20 min.

5: 1.) borane, 2.) sodium hydroxide, 30percent hydrogen peroxide / 1.) THF, R_.T_. 1.5 h, methanol, 2.) 0 degC, 15 min., sodium sulfite

6: 95 percent / pyridine / 72 h / 0 °C

7: 28 percent / sodium azide / dimethylformamide / 1 h / 125 °C

8: 89 percent / 3N hydrochloric acid / methanol / 2.5 h / Ambient temperature

9: 96 percent / 1.) diisopropylamine, n-butyllithium / tetrahydrofuran; hexane / 1.) 0 degC, 15 min., 2.) -78 degC, 35 min.

10: H₂ / platinum oxide / methanol / 1 h / 1551.4 Torr

11: 45 percent / CH₂Cl₂ / Ambient temperature

With hydrogenchloride; sodium hydroxide; n-butyllithium; sodium azide; jones reagent; borane; hydrogen; dihydrogen peroxide; toluene-4-sulfonic acid; diisopropylamine; diborane; platinum(IV) oxide; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1139/v82-151

upstream raw materials:

Boc-Tyr-OH

Z-3-(3'-methylthio-1'-carbomethoxypropylidinyl)-5β-aminomethyl-8a-phenylmethyl-trans-perhydronaphthalene

2-benzylcyclohexan-1-one

4-Methylsulfanyl-2-trimethylsilanyl-butyric acid

Downstream raw materials:

trans-methyl-2-(decahydro-4β-(phenylmethyl)-8β-(L-tyrosylaminomethyl)-2-naphthalenylidene)-4-(methylthio)butanoate HCl monohydrate

trans-methyl-2-(decahydro-4β-(phenylmethyl)-8β-(L-tyrosylaminomethyl)-2-naphthalenylidene)-4-(methylthio)butanoate HCl monohydrate

trans-methyl-2-(decahydro-4β-(phenylmethyl)-8β-(L-tyrosylaminomethyl)-2-naphthalenylidene)-4-(methylthio)butanoate HCl monohydrate

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