(3aR,5aR,5bR,8aR,9aR,9bS)-5b-Benzyloxymethyl-3-bromomethyl-9a-hydroxy-3,5a,7,7-tetramethyl-3,3a,5a,5b,8a,9,9a,9b-octahydro-2,6,8-trioxa-cyclopenta[b]-as-indacen-1-one

Base Information

Chemical Name:(3aR,5aR,5bR,8aR,9aR,9bS)-5b-Benzyloxymethyl-3-bromomethyl-9a-hydroxy-3,5a,7,7-tetramethyl-3,3a,5a,5b,8a,9,9a,9b-octahydro-2,6,8-trioxa-cyclopenta[b]-as-indacen-1-one
CAS No.:244170-99-8
Molecular Formula:C₂₅H₃₁BrO₆
Molecular Weight:507.422
Hs Code.:

(3aR,5aR,5bR,8aR,9aR,9bS)-5b-Benzyloxymethyl-3-bromomethyl-9a-hydroxy-3,5a,7,7-tetramethyl-3,3a,5a,5b,8a,9,9a,9b-octahydro-2,6,8-trioxa-cyclopenta[b]-as-indacen-1-one

Synonyms:(3aR,5aR,5bR,8aR,9aR,9bS)-5b-Benzyloxymethyl-3-bromomethyl-9a-hydroxy-3,5a,7,7-tetramethyl-3,3a,5a,5b,8a,9,9a,9b-octahydro-2,6,8-trioxa-cyclopenta[b]-as-indacen-1-one

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Chemical Property of (3aR,5aR,5bR,8aR,9aR,9bS)-5b-Benzyloxymethyl-3-bromomethyl-9a-hydroxy-3,5a,7,7-tetramethyl-3,3a,5a,5b,8a,9,9a,9b-octahydro-2,6,8-trioxa-cyclopenta[b]-as-indacen-1-one

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Technology Process of (3aR,5aR,5bR,8aR,9aR,9bS)-5b-Benzyloxymethyl-3-bromomethyl-9a-hydroxy-3,5a,7,7-tetramethyl-3,3a,5a,5b,8a,9,9a,9b-octahydro-2,6,8-trioxa-cyclopenta[b]-as-indacen-1-one

There total 14 articles about (3aR,5aR,5bR,8aR,9aR,9bS)-5b-Benzyloxymethyl-3-bromomethyl-9a-hydroxy-3,5a,7,7-tetramethyl-3,3a,5a,5b,8a,9,9a,9b-octahydro-2,6,8-trioxa-cyclopenta[b]-as-indacen-1-one 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: 85.0%

: 244170-98-7
(3aR,3bR,6R,7S,7aR,8aR)-3a-Benzyloxymethyl-7a-hydroxy-6-isopropenyl-2,2,3b-trimethyl-3b,6,7,7a,8,8a-hexahydro-3aH-indeno[1,2-d][1,3]dioxole-7-carboxylic acid

: 244170-99-8
(3aR,5aR,5bR,8aR,9aR,9bS)-5b-Benzyloxymethyl-3-bromomethyl-9a-hydroxy-3,5a,7,7-tetramethyl-3,3a,5a,5b,8a,9,9a,9b-octahydro-2,6,8-trioxa-cyclopenta[b]-as-indacen-1-one

Guidance literature:: With sodium hydrogencarbonate; pyridinium hydrobromide perbromide; In tetrahydrofuran; Ambient temperature;

Reference yield:

: (4R,5R,6S,2'RS)-1-methyl-4-isopropenyl-5-(4''-methoxybenzyloxy)methoxymethyl-6-(2'-hydroxybut-3'-yn-1'-yl)-6-hydroxycyclohex-1-ene

: 244170-99-8
(3aR,5aR,5bR,8aR,9aR,9bS)-5b-Benzyloxymethyl-3-bromomethyl-9a-hydroxy-3,5a,7,7-tetramethyl-3,3a,5a,5b,8a,9,9a,9b-octahydro-2,6,8-trioxa-cyclopenta[b]-as-indacen-1-one

Guidance literature:: Multi-step reaction with 13 steps

1: imidazole / dimethylformamide / 2.5 h / 60 °C

2: hexamethyldisilazane, pyridine / dimethylformamide / 6.5 h / Ambient temperature

3: Pd(OAc)2, N,N-bis(phenylmethylene)-1,2-ethylene diamine / 1,2-dichloro-ethane / 23 h / 56 °C

4: KF*2H₂O, n-Bu₄NCl / acetonitrile / 24 h / Heating

5: 63 percent / Ph₃P, DEAD

6: 63 percent / NaOH

7: 83 percent / VO(acac)2, t-BuOOH / CH₂Cl₂ / Ambient temperature

8: 78 percent / Ti(OBn)4 / 60 °C

9: 94 percent / TsOH / acetone / Ambient temperature

10: 74 percent / aq. DDQ / CH₂Cl₂ / Ambient temperature

11: (COCl)2, DMSO, TEA / -78 - 20 °C

12: aq. NaClO₂, NaH₂PO₄, 2-methyl-but-2-ene / 2-methyl-propan-2-ol / Ambient temperature

13: 85 percent / Pyr*HBr₃, NaHCO₃ / tetrahydrofuran / Ambient temperature

With pyridine; 1H-imidazole; tetrabutoxytitanium; tert.-butylhydroperoxide; palladium diacetate; potassium fluoride; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; bis(acetylacetonate)oxovanadium; N,N'-bis(benzyliden)ethylendiamine; TEA; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; pyridinium hydrobromide perbromide; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol;

Reference yield:

: (1R,5R,6R)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-but-3-ynyl]-5-isopropenyl-6-(4-methoxy-benzyloxymethoxymethyl)-2-methyl-cyclohex-2-enol

: 244170-99-8
(3aR,5aR,5bR,8aR,9aR,9bS)-5b-Benzyloxymethyl-3-bromomethyl-9a-hydroxy-3,5a,7,7-tetramethyl-3,3a,5a,5b,8a,9,9a,9b-octahydro-2,6,8-trioxa-cyclopenta[b]-as-indacen-1-one

Guidance literature:: Multi-step reaction with 12 steps

1: hexamethyldisilazane, pyridine / dimethylformamide / 6.5 h / Ambient temperature

2: Pd(OAc)2, N,N-bis(phenylmethylene)-1,2-ethylene diamine / 1,2-dichloro-ethane / 23 h / 56 °C

3: KF*2H₂O, n-Bu₄NCl / acetonitrile / 24 h / Heating

4: 63 percent / Ph₃P, DEAD

5: 63 percent / NaOH

6: 83 percent / VO(acac)2, t-BuOOH / CH₂Cl₂ / Ambient temperature

7: 78 percent / Ti(OBn)4 / 60 °C

8: 94 percent / TsOH / acetone / Ambient temperature

9: 74 percent / aq. DDQ / CH₂Cl₂ / Ambient temperature

10: (COCl)2, DMSO, TEA / -78 - 20 °C

11: aq. NaClO₂, NaH₂PO₄, 2-methyl-but-2-ene / 2-methyl-propan-2-ol / Ambient temperature

12: 85 percent / Pyr*HBr₃, NaHCO₃ / tetrahydrofuran / Ambient temperature

With pyridine; tetrabutoxytitanium; tert.-butylhydroperoxide; palladium diacetate; potassium fluoride; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; bis(acetylacetonate)oxovanadium; N,N'-bis(benzyliden)ethylendiamine; TEA; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; pyridinium hydrobromide perbromide; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol;