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

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

CAS No.:236746-00-2
Molecular Formula:C₃₅H₄₄O₆
Molecular Weight:560.731
Hs Code.:

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

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

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

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Technology Process of (4S,4aS,5R,6aS,8S,9S,11aS,11bS)-5-benzoyloxy-4-(benzyloxymethyl)oxy-8-hydroxy-4-methoxycarbonyl-9,11b-dimethyl-1,2,3,4,4a,5,6,6a,7,8,9,10,11,11b-tetradecahydro-9,11a-methano-11aH-cyclohepta naphthalene

There total 47 articles about (4S,4aS,5R,6aS,8S,9S,11aS,11bS)-5-benzoyloxy-4-(benzyloxymethyl)oxy-8-hydroxy-4-methoxycarbonyl-9,11b-dimethyl-1,2,3,4,4a,5,6,6a,7,8,9,10,11,11b-tetradecahydro-9,11a-methano-11aH-cyclohepta naphthalene 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: 98.0%

: 236745-99-6
(4S,4aS,5R,6aS,8S,9S,11aS,11bS)-5-benzoyloxy-4-(benzyloxymethyl)oxy-4-methoxycarbonyl-8-(methoxymethyl)oxy-9,11b-dimethyl-1,2,3,4,4a,5,6,6a,7,8,9,10,11,11b-tetrahydro-9,11a-methano-11aH-cyclohepta naphthalene

: 236746-00-2
(4S,4aS,5R,6aS,8S,9S,11aS,11bS)-5-benzoyloxy-4-(benzyloxymethyl)oxy-8-hydroxy-4-methoxycarbonyl-9,11b-dimethyl-1,2,3,4,4a,5,6,6a,7,8,9,10,11,11b-tetradecahydro-9,11a-methano-11aH-cyclohepta naphthalene

Guidance literature:: With hydrogenchloride; In methanol; at 70 ℃; for 0.75h;
DOI:10.1021/ja990404v

Reference yield:

: 172906-75-1
2-methyl-2-propen-1-yl diazoacetate

: 236746-00-2
(4S,4aS,5R,6aS,8S,9S,11aS,11bS)-5-benzoyloxy-4-(benzyloxymethyl)oxy-8-hydroxy-4-methoxycarbonyl-9,11b-dimethyl-1,2,3,4,4a,5,6,6a,7,8,9,10,11,11b-tetradecahydro-9,11a-methano-11aH-cyclohepta naphthalene

Guidance literature:: Multi-step reaction with 31 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

11: 94 percent / aq. NaOH / 23 °C

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

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; sodium hydroxide; N-iodo-succinimide; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; <(R,R)-bis-C(CH3)2>*CuOTf; 4 A molecular sieve; Amberlyst-15 acidic resin; tetrabutyl ammonium fluoride; tert.-butyl lithium; potassium hexamethylsilazane; sodium hydrogencarbonate; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; silver carbonate; lithium bromide; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja990404v

Reference yield:

: 169532-07-4
(1S,5R)-5-methyl-2-oxo-3-oxabicyclo<3.1.0>hexane

: 236746-00-2
(4S,4aS,5R,6aS,8S,9S,11aS,11bS)-5-benzoyloxy-4-(benzyloxymethyl)oxy-8-hydroxy-4-methoxycarbonyl-9,11b-dimethyl-1,2,3,4,4a,5,6,6a,7,8,9,10,11,11b-tetradecahydro-9,11a-methano-11aH-cyclohepta naphthalene

Guidance literature:: Multi-step reaction with 30 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

10: 94 percent / aq. NaOH / 23 °C

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

12: 97 percent / imidazole / dimethylformamide / 8.5 h / Ambient temperature

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

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

15: 95 percent / N-methylmorpholine N-oxide, tetra-n-propylammonium perruthenate / CH₂Cl₂; acetonitrile / 0.5 h / Ambient temperature

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

17: 92 percent / 2-methoxy-1,3-dioxolane, Amberlyst-15 acidic resin / acetonitrile / 12 h / Ambient temperature

18: 99 percent / m-chloroperbenzoic acid, NaHCO₃ / CH₂Cl₂ / 3 h / 0 - 20 °C

19: 90 percent / LiAlH₄ / diethyl ether; tetrahydrofuran / 14 h / Ambient temperature

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

21: 92 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 7 h / Ambient temperature

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

23: 1M aq. HCl / tetrahydrofuran / 0.25 h / Ambient temperature

24: 90 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / -78 °C

25: 97 percent / pyridine, DMAP / CH₂Cl₂ / 2 h / 0 °C

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

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

28: diethyl ether / 0.5 h / 0 °C

29: 88 percent / DMAP, pyridine / 5 h / 100 °C

30: 98 percent / aq. HCl / methanol / 0.75 h / 70 °C

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; sodium hydroxide; N-iodo-succinimide; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; 4 A molecular sieve; Amberlyst-15 acidic resin; tetrabutyl ammonium fluoride; tert.-butyl lithium; potassium hexamethylsilazane; sodium hydrogencarbonate; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; silver carbonate; lithium bromide; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja990404v