1-Cyclohexene-1-carboxylic acid, 4-(acetylamino)-3-(1-methylethoxy)-5-(2-oxoethyl)-, 2-(trimethylsilyl)ethyl ester, (3R,4R,5R)-

Base Information

• Chemical Name: 1-Cyclohexene-1-carboxylic acid, 4-(acetylamino)-3-(1-methylethoxy)-5-(2-oxoethyl)-, 2-(trimethylsilyl)ethyl ester, (3R,4R,5R)-
• CAS No.: 335417-98-6
• Molecular Formula: C19H33NO5Si
• Molecular Weight: 383.56

Synonyms:

Chemical Property of 1-Cyclohexene-1-carboxylic acid, 4-(acetylamino)-3-(1-methylethoxy)-5-(2-oxoethyl)-, 2-(trimethylsilyl)ethyl ester, (3R,4R,5R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-Cyclohexene-1-carboxylic acid, 4-(acetylamino)-3-(1-methylethoxy)-5-(2-oxoethyl)-, 2-(trimethylsilyl)ethyl ester, (3R,4R,5R)-

There total 20 articles about 1-Cyclohexene-1-carboxylic acid, 4-(acetylamino)-3-(1-methylethoxy)-5-(2-oxoethyl)-, 2-(trimethylsilyl)ethyl ester, (3R,4R,5R)- 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-(trimethylsilyl)ethyl (3R,4R,5R)-4-(acetylamino)-5-(2,3-dihydroxypropyl)-3-isopropoxy-1-cyclohexene-1-carboxylate (335417-96-4) → 2-(trimethylsilyl)ethyl (3R,4R,5R)-4-(acetylamino)-3-isopropoxy-5-(2-oxoethyl)-1-cyclohexene-1-carboxylate (335417-98-6)

Guidance literature:

With sodium periodate; In methanol; water;

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

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) → 2-(trimethylsilyl)ethyl (3R,4R,5R)-4-(acetylamino)-3-isopropoxy-5-(2-oxoethyl)-1-cyclohexene-1-carboxylate (335417-98-6)

Guidance literature:

Multi-step reaction with 18 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

With pyridine; lithium hydroxide; sodium periodate; N-Bromosuccinimide; osmium(VIII) oxide; sodium azide; N-methyl-2-indolinone; 2,2'-azobis(isobutyronitrile); 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;

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

Reference yield:

D-(-)-quinic acid (77-95-2) → 2-(trimethylsilyl)ethyl (3R,4R,5R)-4-(acetylamino)-3-isopropoxy-5-(2-oxoethyl)-1-cyclohexene-1-carboxylate (335417-98-6)

Guidance literature:

Multi-step reaction with 19 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

With pyridine; lithium hydroxide; sodium periodate; N-Bromosuccinimide; osmium(VIII) oxide; sodium azide; N-methyl-2-indolinone; 2,2'-azobis(isobutyronitrile); 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;

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

upstream raw materials:

2-(trimethylsilyl)ethyl (3R,4R,5R)-4-(acetylamino)-5-(2,3-dihydroxypropyl)-3-isopropoxy-1-cyclohexene-1-carboxylate

(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

Downstream raw materials:

(3R,4R,5R)-4-Acetylamino-3-isopropoxy-5-methoxycarbonylmethyl-cyclohex-1-enecarboxylic acid 2-trimethylsilanyl-ethyl ester

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