4-Nitro-benzoic acid (S)-6-[1,3]dioxolan-2-yl-1-((R)-4-methyl-7-methylene-cyclohept-3-enylmethyl)-hex-2-ynyl ester

Base Information

• Chemical Name: 4-Nitro-benzoic acid (S)-6-[1,3]dioxolan-2-yl-1-((R)-4-methyl-7-methylene-cyclohept-3-enylmethyl)-hex-2-ynyl ester
• CAS No.: 236746-37-5
• Molecular Formula: C₂₆H₃₁NO₆
• Molecular Weight: 453.535

Synonyms:4-Nitro-benzoic acid (S)-6-[1,3]dioxolan-2-yl-1-((R)-4-methyl-7-methylene-cyclohept-3-enylmethyl)-hex-2-ynyl ester

Chemical Property of 4-Nitro-benzoic acid (S)-6-[1,3]dioxolan-2-yl-1-((R)-4-methyl-7-methylene-cyclohept-3-enylmethyl)-hex-2-ynyl ester

Chemical Property:

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Technology Process of 4-Nitro-benzoic acid (S)-6-[1,3]dioxolan-2-yl-1-((R)-4-methyl-7-methylene-cyclohept-3-enylmethyl)-hex-2-ynyl ester

There total 16 articles about 4-Nitro-benzoic acid (S)-6-[1,3]dioxolan-2-yl-1-((R)-4-methyl-7-methylene-cyclohept-3-enylmethyl)-hex-2-ynyl 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: 67.0%

(R)-7-[1,3]Dioxolan-2-yl-1-((R)-4-methyl-7-methylene-cyclohept-3-enyl)-hept-3-yn-2-ol (236745-87-2) + 4-nitro-benzoic acid (62-23-7) → 4-Nitro-benzoic acid (S)-6-[1,3]dioxolan-2-yl-1-((R)-4-methyl-7-methylene-cyclohept-3-enylmethyl)-hex-2-ynyl ester (236746-37-5)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; at 0 ℃;

DOI:10.1021/ja990404v

Reference yield:

(1S,5R)-5-methyl-2-oxo-3-oxabicyclo<3.1.0>hexane (169532-07-4) → 4-Nitro-benzoic acid (S)-6-[1,3]dioxolan-2-yl-1-((R)-4-methyl-7-methylene-cyclohept-3-enylmethyl)-hex-2-ynyl ester (236746-37-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) MeAl / 1.) toluene, from 0 deg C to RT, 30 min, 2.) toluene, RT, 30 min

2: 92 percent / N-methylmorpholine-N-oxide, tetra-n-propylammonium perruthenate, 4 Angstroem sieves / CH₂Cl₂; acetonitrile / 0.5 h / Ambient temperature

3: 1.) potassium hexamethyldisilazide / 1.) toluene, THF, from 0 deg C to RT, 30 min, 2.) toluene, THF, from -78 deg C to 0 deg C, 1 h

4: 1.) t-BuLi / 1.) ether, -78 deg C, 2.) ether

5: 1.) LDA, HMPA / 1.) THF, -78 deg C, 2.) THF, from -78 deg C to 0 deg C

6: aq. HCl

7: 71 percent / tetrahydrofuran / 0 °C

8: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 23 °C

9: 67 percent / DEAD, PPh₃ / 0 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; tetrapropylammonium perruthennate; 4 A molecular sieve; tetrabutyl ammonium fluoride; tert.-butyl lithium; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/ja990404v

Reference yield:

2-methyl-2-propen-1-yl diazoacetate (172906-75-1) → 4-Nitro-benzoic acid (S)-6-[1,3]dioxolan-2-yl-1-((R)-4-methyl-7-methylene-cyclohept-3-enylmethyl)-hex-2-ynyl ester (236746-37-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 62 percent / <(R,R)-bis2O-)>-C(CH₃)2>*CuOTf / CHCl₃ / Ambient temperature

2: 1.) MeAl / 1.) toluene, from 0 deg C to RT, 30 min, 2.) toluene, RT, 30 min

3: 92 percent / N-methylmorpholine-N-oxide, tetra-n-propylammonium perruthenate, 4 Angstroem sieves / CH₂Cl₂; acetonitrile / 0.5 h / Ambient temperature

4: 1.) potassium hexamethyldisilazide / 1.) toluene, THF, from 0 deg C to RT, 30 min, 2.) toluene, THF, from -78 deg C to 0 deg C, 1 h

5: 1.) t-BuLi / 1.) ether, -78 deg C, 2.) ether

6: 1.) LDA, HMPA / 1.) THF, -78 deg C, 2.) THF, from -78 deg C to 0 deg C

7: aq. HCl

8: 71 percent / tetrahydrofuran / 0 °C

9: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 23 °C

10: 67 percent / DEAD, PPh₃ / 0 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; tetrapropylammonium perruthennate; <(R,R)-bis-C(CH3)2>*CuOTf; 4 A molecular sieve; tetrabutyl ammonium fluoride; tert.-butyl lithium; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; chloroform; acetonitrile;

DOI:10.1021/ja990404v

upstream raw materials:

(R)-7-[1,3]Dioxolan-2-yl-1-((R)-4-methyl-7-methylene-cyclohept-3-enyl)-hept-3-yn-2-ol

4-nitro-benzoic acid

2-methyl-2-propen-1-yl diazoacetate

(1S,5R)-5-methyl-2-oxo-3-oxabicyclo<3.1.0>hexane

Downstream raw materials:

(-)-scopadulcic acid A

(4S,4aS,5R,6aS,8S,9S,11aS,11bS)-4-(benzyloxymethyl)oxy-5-hydroxy-4-methoxycarbonyl-8-(methoxymethyl)oxy-9,11b-dimethyl-1,2,3,4,4a,5,6,6a,7,8,9,10,11,11b-tetradecahydro-9,11a-methano-11aH-cycloheptanaphthalene

(4S,4aS,5R,6aS,8S,11aS,11bS)-4-(benzyloxymethyl)oxy-4-cyano-8-(methoxymethyl)oxy-9,11b-dimethyl-5-trimethylsiloxy-1,2,3,4,4a,5,6,6a,7,8,9,10,11,11b-tetradecahydro-9,11a-methano-11aH-cycloheptanaphthalene

(4S,4aS,5R,6aS,9S,11aS,11bS)-5-benzoyloxy-4-(benzyloxymethyl)oxy-4-methoxycarbonyl-9,11b-dimethyl-8-oxo-1,2,3,4,4a,5,6,6a,7,8,9,10,11,11b-tetradecahydro-9,11a-methano-11aH-cycloheptanaphthalene

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