(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-carbaldehyde

Base Information

• Chemical Name: (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-carbaldehyde
• CAS No.: 244171-14-0
• Molecular Formula: C₂₅H₃₂O₅
• Molecular Weight: 412.526
• Mol file: 244171-14-0.mol

Synonyms:(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-carbaldehyde

Chemical Property of (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-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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-carbaldehyde

There total 12 articles about (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-carbaldehyde 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:

(4R,5R,6S,2'RS)-1-methyl-4-isopropenyl-5-(4''-methoxybenzyloxy)methoxymethyl-6-(2'-hydroxybut-3'-yn-1'-yl)-6-hydroxycyclohex-1-ene → (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-carbaldehyde (244171-14-0)

Guidance literature:

Multi-step reaction with 11 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

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

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 → (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-carbaldehyde (244171-14-0)

Guidance literature:

Multi-step reaction with 10 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

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

Reference yield:

(4R,5R,6S,1'RS)-1-methyl-4-isopropenyl-5-<(4''-methoxybenzyloxy)methoxymethyl>-6-(1'-tert-butyldimethylsilyloxyprop-3'-ynyl)methyl-6-trimethylsilyloxycyclohex-1-ene (244170-92-1) → (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-carbaldehyde (244171-14-0)

Guidance literature:

Multi-step reaction with 9 steps

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

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

3: 63 percent / Ph₃P, DEAD

4: 63 percent / NaOH

5: 83 percent / VO(acac)2, t-BuOOH / CH₂Cl₂ / Ambient temperature

6: 78 percent / Ti(OBn)4 / 60 °C

7: 94 percent / TsOH / acetone / Ambient temperature

8: 74 percent / aq. DDQ / CH₂Cl₂ / Ambient temperature

9: (COCl)2, DMSO, TEA / -78 - 20 °C

With tetrabutoxytitanium; tert.-butylhydroperoxide; palladium diacetate; potassium fluoride; sodium hydroxide; oxalyl dichloride; bis(acetylacetonate)oxovanadium; N,N'-bis(benzyliden)ethylendiamine; TEA; tetrabutyl-ammonium chloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; In dichloromethane; 1,2-dichloro-ethane; acetone; acetonitrile;

upstream raw materials:

(3aR,3bR,6R,7R,7aR,8aR)-3a-Benzyloxymethyl-7-hydroxymethyl-6-isopropenyl-2,2,3b-trimethyl-3a,3b,6,7,8,8a-hexahydro-indeno[1,2-d][1,3]dioxol-7a-ol

(1R,4S,5S,6S,8S)-1-methyl-4-isopropenyl-5-<(4'-methoxybenzyloxy)methoxymethyl>-6,8-dihydroxy-9-methylene-cis-bicyclo<4.3.0^1,6>non-2-ene

(1R,4S,5S,6S,8R)-1-methyl-4-isopropenyl-5-<(4'-methoxybenzyloxy)methoxymethyl>-6,8-dihydroxy-9-methylene-cis-bicyclo<4.3.0^1,6>non-2-ene

(1R,2R,3aR,4R,5R,7aR)-1-Benzyloxymethyl-5-isopropenyl-4-(4-methoxy-benzyloxymethoxymethyl)-7a-methyl-1,2,3,4,5,7a-hexahydro-indene-1,2,3a-triol

Downstream raw materials:

(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

corianine

(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