1-Cyclohexene-1-carboxylic acid, 4-(acetylamino)-3-(1-methylethoxy)-5-(2-propenyl)-, methyl ester, (3R,4R,5S)-

Base Information

• Chemical Name: 1-Cyclohexene-1-carboxylic acid, 4-(acetylamino)-3-(1-methylethoxy)-5-(2-propenyl)-, methyl ester, (3R,4R,5S)-
• CAS No.: 335417-50-0
• Molecular Formula: C16H25NO4
• Molecular Weight: 295.379

Synonyms:

Chemical Property of 1-Cyclohexene-1-carboxylic acid, 4-(acetylamino)-3-(1-methylethoxy)-5-(2-propenyl)-, methyl ester, (3R,4R,5S)-

Chemical Property:

Purity/Quality:

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Technology Process of 1-Cyclohexene-1-carboxylic acid, 4-(acetylamino)-3-(1-methylethoxy)-5-(2-propenyl)-, methyl ester, (3R,4R,5S)-

There total 16 articles about 1-Cyclohexene-1-carboxylic acid, 4-(acetylamino)-3-(1-methylethoxy)-5-(2-propenyl)-, methyl ester, (3R,4R,5S)- 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) → methyl (3R,4R,5S)-4-(acetylamino)-5-allyl-3-isopropoxy-1-cyclohexene-1-carboxylate (335417-50-0)

Guidance literature:

Multi-step reaction with 14 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

With pyridine; N-Bromosuccinimide; sodium azide; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; potassium carbonate; ammonium chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; benzene;

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

Reference yield:

D-(-)-quinic acid (77-95-2) → methyl (3R,4R,5S)-4-(acetylamino)-5-allyl-3-isopropoxy-1-cyclohexene-1-carboxylate (335417-50-0)

Guidance literature:

Multi-step reaction with 15 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

With pyridine; N-Bromosuccinimide; sodium azide; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; 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; toluene; benzene;

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) → methyl (3R,4R,5S)-4-(acetylamino)-5-allyl-3-isopropoxy-1-cyclohexene-1-carboxylate (335417-50-0)

Guidance literature:

Multi-step reaction with 13 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

With pyridine; sodium azide; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; potassium carbonate; ammonium chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; benzene;

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

upstream raw materials:

acetic anhydride

(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-[2-(4-nitro-phenylselanyl)-ethyl]-cyclohex-1-enecarboxylic acid methyl ester

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

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

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

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