3-Chloro-benzoic acid (1S,2R,3R)-3-(7-methoxy-benzo[1,3]dioxol-5-yl)-2-methoxycarbonylamino-6-oxo-cyclohexyl ester

Base Information

• Chemical Name: 3-Chloro-benzoic acid (1S,2R,3R)-3-(7-methoxy-benzo[1,3]dioxol-5-yl)-2-methoxycarbonylamino-6-oxo-cyclohexyl ester
• CAS No.: 208193-05-9
• Molecular Formula: C₂₃H₂₂ClNO₈
• Molecular Weight: 475.883

Synonyms:3-Chloro-benzoic acid (1S,2R,3R)-3-(7-methoxy-benzo[1,3]dioxol-5-yl)-2-methoxycarbonylamino-6-oxo-cyclohexyl ester

Chemical Property of 3-Chloro-benzoic acid (1S,2R,3R)-3-(7-methoxy-benzo[1,3]dioxol-5-yl)-2-methoxycarbonylamino-6-oxo-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Chloro-benzoic acid (1S,2R,3R)-3-(7-methoxy-benzo[1,3]dioxol-5-yl)-2-methoxycarbonylamino-6-oxo-cyclohexyl ester

There total 13 articles about 3-Chloro-benzoic acid (1S,2R,3R)-3-(7-methoxy-benzo[1,3]dioxol-5-yl)-2-methoxycarbonylamino-6-oxo-cyclohexyl 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: 91.0%

3-Chloro-benzoic acid (1R,2R,3R)-3-(7-methoxy-benzo[1,3]dioxol-5-yl)-2-methoxycarbonylamino-6-oxo-cyclohexyl ester (208193-04-8) → 3-Chloro-benzoic acid (1S,2R,3R)-3-(7-methoxy-benzo[1,3]dioxol-5-yl)-2-methoxycarbonylamino-6-oxo-cyclohexyl ester (208193-05-9)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at 90 ℃; for 4h;

DOI:10.1016/S0040-4020(98)00975-2

Reference yield:

cyclohexanedione monoethylene ketal (4746-97-8) → 3-Chloro-benzoic acid (1S,2R,3R)-3-(7-methoxy-benzo[1,3]dioxol-5-yl)-2-methoxycarbonylamino-6-oxo-cyclohexyl ester (208193-05-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) n-BuLi / 1.) THF, 2.) THF

2: POCl₃, DBU, pyridine

3: H₂ / Pd/C

4: H₃O⁽¹⁺⁾, MeOH

5: lithium (+)-bis(α-methylbenzyl)amide, LiCl / tetrahydrofuran / -78 °C

6: TMSN₃, (PhIO)n / CH₂Cl₂ / -15 °C

7: LiAlH₄ / diethyl ether

8: pyridine

9: imidazole / CH₂Cl₂

10: H₃O⁺

11: t-BuOK / hexamethylphosphoric acid triamide / 90 °C

With pyridine; 1H-imidazole; methanol; lithium aluminium tetrahydride; n-butyllithium; trimethylsilylazide; (+)-bis(α-methylbenzyl)amine lithium salt; (PhIO)n; oxonium; potassium tert-butylate; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane;

DOI:10.1021/ja980407s

Reference yield:

5-bromo-7-methoxy-1,3-benzodioxol (91511-83-0) → 3-Chloro-benzoic acid (1S,2R,3R)-3-(7-methoxy-benzo[1,3]dioxol-5-yl)-2-methoxycarbonylamino-6-oxo-cyclohexyl ester (208193-05-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) n-BuLi / 1.) THF, 2.) THF

2: POCl₃, DBU, pyridine

3: H₂ / Pd/C

4: H₃O⁽¹⁺⁾, MeOH

5: lithium (+)-bis(α-methylbenzyl)amide, LiCl / tetrahydrofuran / -78 °C

6: TMSN₃, (PhIO)n / CH₂Cl₂ / -15 °C

7: LiAlH₄ / diethyl ether

8: pyridine

9: imidazole / CH₂Cl₂

10: H₃O⁺

11: t-BuOK / hexamethylphosphoric acid triamide / 90 °C

With pyridine; 1H-imidazole; methanol; lithium aluminium tetrahydride; n-butyllithium; trimethylsilylazide; (+)-bis(α-methylbenzyl)amine lithium salt; (PhIO)n; oxonium; potassium tert-butylate; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane;

DOI:10.1021/ja980407s

upstream raw materials:

3-Chloro-benzoic acid (1R,2R,3R)-3-(7-methoxy-benzo[1,3]dioxol-5-yl)-2-methoxycarbonylamino-6-oxo-cyclohexyl ester

3-chloro-benzenecarboperoxoic acid

3-Chloro-benzoic acid (1R,5R,6R)-5-(7-methoxy-benzo[1,3]dioxol-5-yl)-6-methoxycarbonylamino-2-triisopropylsilanyloxy-cyclohex-2-enyl ester

[(1R,6R)-6-(7-Methoxy-benzo[1,3]dioxol-5-yl)-3-triisopropylsilanyloxy-cyclohex-2-enyl]-carbamic acid methyl ester

Downstream raw materials:

pancratistatin

[(1R,2S,3S,4S,5R,6R)-2,3,4,5-Tetrahydroxy-6-(7-methoxy-benzo[1,3]dioxol-5-yl)-cyclohexyl]-carbamic acid methyl ester

Acetic acid (1R,2S,3S,4S,5R,6R)-2,3,4-triacetoxy-6-(7-methoxy-benzo[1,3]dioxol-5-yl)-5-methoxycarbonylamino-cyclohexyl ester

C₃₂H₃₄ClNO₈SeSi

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