hydroxymethyl 5-(benzoyloxy)-9,11b-dimethyl-8-oxotetradecahydro-9,11a-methanocyclohepta[a]naphthalene-4-carboxylate

Base Information

Chemical Name:hydroxymethyl 5-(benzoyloxy)-9,11b-dimethyl-8-oxotetradecahydro-9,11a-methanocyclohepta[a]naphthalene-4-carboxylate
CAS No.:114804-64-7
Molecular Formula:C27H34 O6
Molecular Weight:454.563
Hs Code.:

Synonyms:9,11a-Methano-11aH-cyclohepta[a]naphthalene-4-carboxylicacid, 5-(benzoyloxy)tetradecahydro-4-(hydroxymethyl)-9,11b-dimethyl-8-oxo-,[4S-(4a,4ab,5a,6aa,9a,11aa,11ba)]-; Scopadulcic acid A

Suppliers and Price of hydroxymethyl 5-(benzoyloxy)-9,11b-dimethyl-8-oxotetradecahydro-9,11a-methanocyclohepta[a]naphthalene-4-carboxylate

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of hydroxymethyl 5-(benzoyloxy)-9,11b-dimethyl-8-oxotetradecahydro-9,11a-methanocyclohepta[a]naphthalene-4-carboxylate

Chemical Property:

Vapor Pressure:1.77E-14mmHg at 25°C
Boiling Point:583.9°C at 760 mmHg
Flash Point:191.6°C
Density:1.25g/cm³

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Technology Process of hydroxymethyl 5-(benzoyloxy)-9,11b-dimethyl-8-oxotetradecahydro-9,11a-methanocyclohepta[a]naphthalene-4-carboxylate

There total 50 articles about hydroxymethyl 5-(benzoyloxy)-9,11b-dimethyl-8-oxotetradecahydro-9,11a-methanocyclohepta[a]naphthalene-4-carboxylate 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: 90.0%

: C₃₄H₄₀O₆

: 114804-64-7
(-)-scopadulcic acid A

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; for 9h; Ambient temperature;
DOI:10.1021/ja990404v

Reference yield:

: lithium 2-(4'-pentynyl)-1,3-dioxolane

: 114804-64-7
(-)-scopadulcic acid A

Guidance literature:: Multi-step reaction with 34 steps

1: 81 percent / tetrahydrofuran / -78 - 23 °C

2: 94 percent / N-methylmorpholine-N-oxide, tetra-n-propylammonium perruthenate / CH₂Cl₂; acetonitrile

3: (R)-B-isopinocampheyl-9-borabicyclo<3.3.1>nonane

4: imidazole

5: aq. AcOH

6: I₂, Ph₃P, imidazole

7: 1.) t-BuLi / 1.) ether, -78 deg C, 30 min, 2.) ether, from -78 deg C to 0 deg C, 1.5 h

8: 1.) LDA / 1.) hexane, THF, -78 deg C, 5 min, 2.) hexane, THF, from -78 deg C to 0 deg C, 60 min

9: 5 percent aq. HCl / tetrahydrofuran / 1 h / Ambient temperature

10: 1.) sec-BuLi / 1.) cyclohexane, THF, 0 deg C, 30 min, 2.) cyclohexane, from -78 deg C to 0 deg C, 1 h

11: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

12: 1.) Red-Al, 2.) N-iodosuccinimide / 1.) THF, Et₂O, RT, 15 h, 2.) THF, Et₂O, 0 deg C, 5 min

13: 97 percent / imidazole / dimethylformamide / 8.5 h / Ambient temperature

14: Ph₃P, Pd(OAc)2, Ag₂CO₃ / tetrahydrofuran / 18 h / 65 °C

15: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / Ambient temperature

16: 95 percent / N-methylmorpholine N-oxide, tetra-n-propylammonium perruthenate / CH₂Cl₂; acetonitrile / 0.5 h / Ambient temperature

17: 1.) LiBr, Ni(acac)2 / 1.) Et₂O, 0 deg C, 10 min, 2.) Et₂O, RT, 17 h

18: 92 percent / 2-methoxy-1,3-dioxolane, Amberlyst-15 acidic resin / acetonitrile / 12 h / Ambient temperature

19: 99 percent / m-chloroperbenzoic acid, NaHCO₃ / CH₂Cl₂ / 3 h / 0 - 20 °C

20: 90 percent / LiAlH₄ / diethyl ether; tetrahydrofuran / 14 h / Ambient temperature

21: 74 percent / 20 percent aq. HCl / tetrahydrofuran / 12 h / 50 °C

22: 92 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 7 h / Ambient temperature

23: 2.) Et₃N / 1.) toluene, THF, 0 deg C, 10 h, 2.) THF, from 0 deg C to RT

24: 1M aq. HCl / tetrahydrofuran / 0.25 h / Ambient temperature

25: 90 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / -78 °C

26: 97 percent / pyridine, DMAP / CH₂Cl₂ / 2 h / 0 °C

27: 1.) LDA / 1.) hexane, THF, 0 deg C, 15 min, 2.) hexane, THF, 0 deg C, 2 h

28: K₂CO₃, KOH / methanol / 24 h / 140 °C

29: diethyl ether / 0.5 h / 0 °C

30: 88 percent / DMAP, pyridine / 5 h / 100 °C

31: 98 percent / aq. HCl / methanol / 0.75 h / 70 °C

32: 90 percent / pyridinium chlorochromate, 4 Angstroem sives / CH₂Cl₂ / 2.5 h / Ambient temperature

33: 72 percent / lithium n-propylmercaptide, HMPA / benzene / 8 h / Ambient temperature

34: 90 percent / H₂ / 10 percent Pd/C / methanol / 9 h / Ambient temperature

With 2-methoxy-1,3-dioxolane; pyridine; 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; palladium diacetate; bis(acetylacetonate)nickel(II); potassium hydroxide; N-iodo-succinimide; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; B-isopinocampheyl-9-borabicyclo[3.3.1]nonane; 4 Angstroem sives; Amberlyst-15 acidic resin; tetrabutyl ammonium fluoride; hydrogen; iodine; tert.-butyl lithium; sec.-butyllithium; lithium n-propylmercaptide; sodium hydrogencarbonate; potassium carbonate; acetic acid; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; silver carbonate; pyridinium chlorochromate; lithium bromide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/ja990404v

Reference yield:

: 236745-45-2
1-(tert-butyl-dimethyl-silanyloxy)-8-[1,3]dioxolan-2-yl-oct-4-yn-3-one

: 114804-64-7
(-)-scopadulcic acid A

Guidance literature:: Multi-step reaction with 32 steps

1: (R)-B-isopinocampheyl-9-borabicyclo<3.3.1>nonane

2: imidazole

3: aq. AcOH

4: I₂, Ph₃P, imidazole

5: 1.) t-BuLi / 1.) ether, -78 deg C, 30 min, 2.) ether, from -78 deg C to 0 deg C, 1.5 h

6: 1.) LDA / 1.) hexane, THF, -78 deg C, 5 min, 2.) hexane, THF, from -78 deg C to 0 deg C, 60 min

7: 5 percent aq. HCl / tetrahydrofuran / 1 h / Ambient temperature

8: 1.) sec-BuLi / 1.) cyclohexane, THF, 0 deg C, 30 min, 2.) cyclohexane, from -78 deg C to 0 deg C, 1 h

9: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

10: 1.) Red-Al, 2.) N-iodosuccinimide / 1.) THF, Et₂O, RT, 15 h, 2.) THF, Et₂O, 0 deg C, 5 min

11: 97 percent / imidazole / dimethylformamide / 8.5 h / Ambient temperature

12: Ph₃P, Pd(OAc)2, Ag₂CO₃ / tetrahydrofuran / 18 h / 65 °C

13: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / Ambient temperature

14: 95 percent / N-methylmorpholine N-oxide, tetra-n-propylammonium perruthenate / CH₂Cl₂; acetonitrile / 0.5 h / Ambient temperature

15: 1.) LiBr, Ni(acac)2 / 1.) Et₂O, 0 deg C, 10 min, 2.) Et₂O, RT, 17 h

16: 92 percent / 2-methoxy-1,3-dioxolane, Amberlyst-15 acidic resin / acetonitrile / 12 h / Ambient temperature

17: 99 percent / m-chloroperbenzoic acid, NaHCO₃ / CH₂Cl₂ / 3 h / 0 - 20 °C

18: 90 percent / LiAlH₄ / diethyl ether; tetrahydrofuran / 14 h / Ambient temperature

19: 74 percent / 20 percent aq. HCl / tetrahydrofuran / 12 h / 50 °C

20: 92 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 7 h / Ambient temperature

21: 2.) Et₃N / 1.) toluene, THF, 0 deg C, 10 h, 2.) THF, from 0 deg C to RT

22: 1M aq. HCl / tetrahydrofuran / 0.25 h / Ambient temperature

23: 90 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / -78 °C

24: 97 percent / pyridine, DMAP / CH₂Cl₂ / 2 h / 0 °C

25: 1.) LDA / 1.) hexane, THF, 0 deg C, 15 min, 2.) hexane, THF, 0 deg C, 2 h

26: K₂CO₃, KOH / methanol / 24 h / 140 °C

27: diethyl ether / 0.5 h / 0 °C

28: 88 percent / DMAP, pyridine / 5 h / 100 °C

29: 98 percent / aq. HCl / methanol / 0.75 h / 70 °C

30: 90 percent / pyridinium chlorochromate, 4 Angstroem sives / CH₂Cl₂ / 2.5 h / Ambient temperature

31: 72 percent / lithium n-propylmercaptide, HMPA / benzene / 8 h / Ambient temperature

32: 90 percent / H₂ / 10 percent Pd/C / methanol / 9 h / Ambient temperature

With 2-methoxy-1,3-dioxolane; pyridine; 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; palladium diacetate; bis(acetylacetonate)nickel(II); potassium hydroxide; N-iodo-succinimide; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; B-isopinocampheyl-9-borabicyclo[3.3.1]nonane; 4 Angstroem sives; Amberlyst-15 acidic resin; tetrabutyl ammonium fluoride; hydrogen; iodine; tert.-butyl lithium; sec.-butyllithium; lithium n-propylmercaptide; sodium hydrogencarbonate; potassium carbonate; acetic acid; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; silver carbonate; pyridinium chlorochromate; lithium bromide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/ja990404v