(-)-(4R)-4-{(2R)-2-{[(tert-butyl)diphenylsilyl]oxy}heptyl}hexahydro-5-tosyl-1,5-diazocin(1H)-2-one

Base Information

• Chemical Name: (-)-(4R)-4-{(2R)-2-{[(tert-butyl)diphenylsilyl]oxy}heptyl}hexahydro-5-tosyl-1,5-diazocin(1H)-2-one
• CAS No.: 524011-12-9
• Molecular Formula: C₃₆H₅₀N₂O₄SSi
• Molecular Weight: 634.956
• Mol file: 524011-12-9.mol

Synonyms:(-)-(4R)-4-{(2R)-2-{[(tert-butyl)diphenylsilyl]oxy}heptyl}hexahydro-5-tosyl-1,5-diazocin(1H)-2-one

Chemical Property of (-)-(4R)-4-{(2R)-2-{[(tert-butyl)diphenylsilyl]oxy}heptyl}hexahydro-5-tosyl-1,5-diazocin(1H)-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(4R)-4-{(2R)-2-{[(tert-butyl)diphenylsilyl]oxy}heptyl}hexahydro-5-tosyl-1,5-diazocin(1H)-2-one

There total 11 articles about (-)-(4R)-4-{(2R)-2-{[(tert-butyl)diphenylsilyl]oxy}heptyl}hexahydro-5-tosyl-1,5-diazocin(1H)-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: 95.0%

methyl (-)-(3R,5R)-3-{[(3-aminopropyl)tosyl]amino}-5-{[(tert-butyl)diphenylsilyl]oxy}decanoate (524011-11-8) → (-)-(4R)-4-{(2R)-2-{[(tert-butyl)diphenylsilyl]oxy}heptyl}hexahydro-5-tosyl-1,5-diazocin(1H)-2-one (524011-12-9)

Guidance literature:

With 4 A molecular sieve; triethoxyantimony; In benzene; Heating;

DOI:10.1002/hlca.200390016

Reference yield:

(3R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]octanal (111633-54-6) → (-)-(4R)-4-{(2R)-2-{[(tert-butyl)diphenylsilyl]oxy}heptyl}hexahydro-5-tosyl-1,5-diazocin(1H)-2-one (524011-12-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 1 h / 20 °C

2.1: 637 mg / p-toluenesulfonic acid monohydrate / methanol / 1 h / 20 °C

3.1: CH₂Cl₂ / 1 h / -78 - -60 °C

3.2: 94 percent / H₂O / CH₂Cl₂ / 4 h / 60 °C

4.1: 80 percent / potassium tert-butoxide / tetrahydrofuran / 2.5 h / 0 °C

5.1: 73 percent / cesium carbonate / dimethylformamide / 20 °C

6.1: 93 percent / trifluoroacetic acid / toluene / 50 °C

7.1: 95 percent / Sb(OEt)3; 4 Angstroem molecular sieves / benzene / Heating

With 4 A molecular sieve; triethoxyantimony; potassium tert-butylate; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; lithium chloride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; benzene; 1.1: Horner-Wadsworth-Emmons reaction / 4.1: aza-Michael cyclization;

DOI:10.1002/hlca.200390016

Reference yield:

(3R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]octanol → (-)-(4R)-4-{(2R)-2-{[(tert-butyl)diphenylsilyl]oxy}heptyl}hexahydro-5-tosyl-1,5-diazocin(1H)-2-one (524011-12-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 1.10 g / PDC / CH₂Cl₂ / 4 h / Heating

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 1 h / 20 °C

3.1: 637 mg / p-toluenesulfonic acid monohydrate / methanol / 1 h / 20 °C

4.1: CH₂Cl₂ / 1 h / -78 - -60 °C

4.2: 94 percent / H₂O / CH₂Cl₂ / 4 h / 60 °C

5.1: 80 percent / potassium tert-butoxide / tetrahydrofuran / 2.5 h / 0 °C

6.1: 73 percent / cesium carbonate / dimethylformamide / 20 °C

7.1: 93 percent / trifluoroacetic acid / toluene / 50 °C

8.1: 95 percent / Sb(OEt)3; 4 Angstroem molecular sieves / benzene / Heating

With dipyridinium dichromate; 4 A molecular sieve; triethoxyantimony; potassium tert-butylate; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; lithium chloride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; benzene; 2.1: Horner-Wadsworth-Emmons reaction / 5.1: aza-Michael cyclization;

DOI:10.1002/hlca.200390016

upstream raw materials:

methyl (-)-(3R,5R)-3-{[(3-aminopropyl)tosyl]amino}-5-{[(tert-butyl)diphenylsilyl]oxy}decanoate

(3R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]octanal

p-toluenesulfonyl chloride

tert-butylchlorodiphenylsilane