3-Cyclohexene-1-acetic acid, 6-(acetylamino)-5-(1-methylethoxy)-3-[[2-(trimethylsilyl)ethoxy]carbonyl]-, methyl ester, (1R,5R,6R)-

Base Information

• Chemical Name: 3-Cyclohexene-1-acetic acid, 6-(acetylamino)-5-(1-methylethoxy)-3-[[2-(trimethylsilyl)ethoxy]carbonyl]-, methyl ester, (1R,5R,6R)-
• CAS No.: 335418-01-4
• Molecular Formula: C20H35NO6Si
• Molecular Weight: 413.587
• Mol file: 335418-01-4.mol

Synonyms:

Chemical Property of 3-Cyclohexene-1-acetic acid, 6-(acetylamino)-5-(1-methylethoxy)-3-[[2-(trimethylsilyl)ethoxy]carbonyl]-, methyl ester, (1R,5R,6R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Cyclohexene-1-acetic acid, 6-(acetylamino)-5-(1-methylethoxy)-3-[[2-(trimethylsilyl)ethoxy]carbonyl]-, methyl ester, (1R,5R,6R)-

There total 21 articles about 3-Cyclohexene-1-acetic acid, 6-(acetylamino)-5-(1-methylethoxy)-3-[[2-(trimethylsilyl)ethoxy]carbonyl]-, methyl ester, (1R,5R,6R)- 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:

(1S,3R,4R,5R)-3,4-O-Benzylidene-1,3,4-trihydroxy-6-oxabicyclo<3.2.1>octan-7-one (216662-57-6) → (3R,4R,5R)-4-Acetylamino-3-isopropoxy-5-methoxycarbonylmethyl-cyclohex-1-enecarboxylic acid 2-trimethylsilanyl-ethyl ester (335418-01-4)

Guidance literature:

Multi-step reaction with 20 steps

1: 80 percent / NBS; AIBN / CCl₄ / Heating

2: 82 percent / AIBN / benzene / Heating

3: 99 percent / Et₃N / CH₂Cl₂

4: 99 percent / K₂CO₃

5: 85 percent / pyridine

6: 99 percent / Et₃N / CH₂Cl₂

7: 99 percent / K₂CO₃ / methanol

8: DBU / tetrahydrofuran / Heating

9: NaN₃; NH₄Cl / methanol; H₂O

10: 99 percent / Et₃N / CH₂Cl₂

11: Ph₃P; Et₃N / H₂O

12: Et₃N / CH₂Cl₂

13: BF₃*Et₂O

14: pyridine

15: 98 percent / LiOH / tetrahydrofuran; H₂O

16: 67 percent / 2-chloro-1-methylpyridinium chloride; Et₃N

17: OsO₄; NMO / acetone; H₂O

18: NaIO₄ / methanol; H₂O

19: NaClO₂; 2-butene / pH 3 - 4

With pyridine; lithium hydroxide; sodium chlorite; sodium periodate; N-Bromosuccinimide; osmium(VIII) oxide; sodium azide; N-methyl-2-indolinone; 2,2'-azobis(isobutyronitrile); butene-2; boron trifluoride diethyl etherate; 1-methyl-2-chloropyridinium chloride; potassium carbonate; ammonium chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; acetone; benzene; 19: Pinnick procedure;

DOI:10.1016/S0960-894X(02)00732-1

Reference yield:

D-(-)-quinic acid (77-95-2) → (3R,4R,5R)-4-Acetylamino-3-isopropoxy-5-methoxycarbonylmethyl-cyclohex-1-enecarboxylic acid 2-trimethylsilanyl-ethyl ester (335418-01-4)

Guidance literature:

Multi-step reaction with 21 steps

1: 84 percent / TsOH / toluene / Heating

2: 80 percent / NBS; AIBN / CCl₄ / Heating

3: 82 percent / AIBN / benzene / Heating

4: 99 percent / Et₃N / CH₂Cl₂

5: 99 percent / K₂CO₃

6: 85 percent / pyridine

7: 99 percent / Et₃N / CH₂Cl₂

8: 99 percent / K₂CO₃ / methanol

9: DBU / tetrahydrofuran / Heating

10: NaN₃; NH₄Cl / methanol; H₂O

11: 99 percent / Et₃N / CH₂Cl₂

12: Ph₃P; Et₃N / H₂O

13: Et₃N / CH₂Cl₂

14: BF₃*Et₂O

15: pyridine

16: 98 percent / LiOH / tetrahydrofuran; H₂O

17: 67 percent / 2-chloro-1-methylpyridinium chloride; Et₃N

18: OsO₄; NMO / acetone; H₂O

19: NaIO₄ / methanol; H₂O

20: NaClO₂; 2-butene / pH 3 - 4

With pyridine; lithium hydroxide; sodium chlorite; sodium periodate; N-Bromosuccinimide; osmium(VIII) oxide; sodium azide; N-methyl-2-indolinone; 2,2'-azobis(isobutyronitrile); butene-2; boron trifluoride diethyl etherate; 1-methyl-2-chloropyridinium chloride; potassium carbonate; ammonium chloride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; acetone; toluene; benzene; 20: Pinnick procedure;

DOI:10.1016/S0960-894X(02)00732-1

Reference yield:

(1R,3S,4S,5R)-3-bromo-1-hydroxy-7-oxo-6-oxabicyclo[3.2.1]oct-4-yl benzoate (105539-78-4) → (3R,4R,5R)-4-Acetylamino-3-isopropoxy-5-methoxycarbonylmethyl-cyclohex-1-enecarboxylic acid 2-trimethylsilanyl-ethyl ester (335418-01-4)

Guidance literature:

Multi-step reaction with 19 steps

1: 82 percent / AIBN / benzene / Heating

2: 99 percent / Et₃N / CH₂Cl₂

3: 99 percent / K₂CO₃

4: 85 percent / pyridine

5: 99 percent / Et₃N / CH₂Cl₂

6: 99 percent / K₂CO₃ / methanol

7: DBU / tetrahydrofuran / Heating

8: NaN₃; NH₄Cl / methanol; H₂O

9: 99 percent / Et₃N / CH₂Cl₂

10: Ph₃P; Et₃N / H₂O

11: Et₃N / CH₂Cl₂

12: BF₃*Et₂O

13: pyridine

14: 98 percent / LiOH / tetrahydrofuran; H₂O

15: 67 percent / 2-chloro-1-methylpyridinium chloride; Et₃N

16: OsO₄; NMO / acetone; H₂O

17: NaIO₄ / methanol; H₂O

18: NaClO₂; 2-butene / pH 3 - 4

With pyridine; lithium hydroxide; sodium chlorite; sodium periodate; osmium(VIII) oxide; sodium azide; N-methyl-2-indolinone; 2,2'-azobis(isobutyronitrile); butene-2; boron trifluoride diethyl etherate; 1-methyl-2-chloropyridinium chloride; potassium carbonate; ammonium chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; acetone; benzene; 18: Pinnick procedure;

DOI:10.1016/S0960-894X(02)00732-1

upstream raw materials:

diazomethane

(1S,3R,4R,5R)-3,4-O-Benzylidene-1,3,4-trihydroxy-6-oxabicyclo<3.2.1>octan-7-one

D-(-)-quinic acid

(1R,3S,4S,5R)-3-bromo-1-hydroxy-7-oxo-6-oxabicyclo[3.2.1]oct-4-yl benzoate