(+)-(5aα,6α,9aβ)-6-<(benzyloxy)methyl>-4,5,5a,6,9,9a-hexahydro-6,9a-dimethylnaphtho<1,2-b>furan-7-one

Base Information

Chemical Name:(+)-(5aα,6α,9aβ)-6-<(benzyloxy)methyl>-4,5,5a,6,9,9a-hexahydro-6,9a-dimethylnaphtho<1,2-b>furan-7-one
CAS No.:116179-56-7
Molecular Formula:C₂₂H₂₆O₃
Molecular Weight:338.447
Hs Code.:

Synonyms:(+)-(5aα,6α,9aβ)-6-<(benzyloxy)methyl>-4,5,5a,6,9,9a-hexahydro-6,9a-dimethylnaphtho<1,2-b>furan-7-one

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Chemical Property of (+)-(5aα,6α,9aβ)-6-<(benzyloxy)methyl>-4,5,5a,6,9,9a-hexahydro-6,9a-dimethylnaphtho<1,2-b>furan-7-one

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Technology Process of (+)-(5aα,6α,9aβ)-6-<(benzyloxy)methyl>-4,5,5a,6,9,9a-hexahydro-6,9a-dimethylnaphtho<1,2-b>furan-7-one

There total 15 articles about (+)-(5aα,6α,9aβ)-6-<(benzyloxy)methyl>-4,5,5a,6,9,9a-hexahydro-6,9a-dimethylnaphtho<1,2-b>furan-7-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: 95.0%

: 116179-55-6
(+)-(5aα,6α,7β,9aβ)-6-<(benzyloxy)methyl>-4,5,5a,6,7,8,9,9a-octahydro-6,9a-dimethylnaphtho<1,2-b>furan-7-ol

: 116179-56-7
(+)-(5aα,6α,9aβ)-6-<(benzyloxy)methyl>-4,5,5a,6,9,9a-hexahydro-6,9a-dimethylnaphtho<1,2-b>furan-7-one

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; In tetrahydrofuran; at -78 - -35 ℃;
DOI:10.1021/jo00256a007

Reference yield:

: 94-48-4
(E)-geranyl benzoate

: 116179-56-7
(+)-(5aα,6α,9aβ)-6-<(benzyloxy)methyl>-4,5,5a,6,9,9a-hexahydro-6,9a-dimethylnaphtho<1,2-b>furan-7-one

Guidance literature:: Multi-step reaction with 10 steps

2: m-chloroperoxybenzoic acid / CH₂Cl₂ / 1.) 0 deg C, 0.5 h, 2.) RT, 2 h

3: 1.) NaH, 2.) n-Bu₄NI / 1.) THF, RT, 20 min, 2.) THF, RT, 5 h

4: 99 percent / CH₃ONa, n-Bu₄NI / methanol / 12 h / Ambient temperature

5: 1.) n-BuLi, hexamethylphosphoramide (HMPA), 2.) pTsCl, LiCl / 1.) ether, hexane, 0 deg C, 10 min, 2.) a) 0 deg C, 1 h, b) RT, 2 h

6: 79 percent / Li₂CuCl₄ / tetrahydrofuran / 0.5 h

7: 72 percent / BF₃*OEt₂, Et₃N / CH₂Cl₂; benzene; hexane / 0.75 h / -78 °C

8: 97 percent / oxalyl chloride, DMSO / tetrahydrofuran / -78 - -35 °C

9: 1.) MgBr₂*OEt₂, 2.) L-Selectride / 1.) CH₂Cl₂, -10 deg C, 5 min, 2.) THF, from -78 deg C to RT, 2 h

10: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) THF, -35 deg C, 5 min, 2.) RT, 1 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; oxalyl dichloride; dilithium tetrachlorocuprate; boron trifluoride diethyl etherate; sodium methylate; tetra-(n-butyl)ammonium iodide; L-Selectride; sodium hydride; dimethyl sulfoxide; triethylamine; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; lithium chloride; magnesium bromide; In tetrahydrofuran; methanol; hexane; dichloromethane; benzene;
DOI:10.1021/jo00256a007

Reference yield:

: 88218-65-9
(2E,6E)-8-hydroxy-3,7-dimethylocta-2,6-dien-1-yl benzoate

: 116179-56-7
(+)-(5aα,6α,9aβ)-6-<(benzyloxy)methyl>-4,5,5a,6,9,9a-hexahydro-6,9a-dimethylnaphtho<1,2-b>furan-7-one

Guidance literature:: Multi-step reaction with 9 steps

1: m-chloroperoxybenzoic acid / CH₂Cl₂ / 1.) 0 deg C, 0.5 h, 2.) RT, 2 h

2: 1.) NaH, 2.) n-Bu₄NI / 1.) THF, RT, 20 min, 2.) THF, RT, 5 h

3: 99 percent / CH₃ONa, n-Bu₄NI / methanol / 12 h / Ambient temperature

4: 1.) n-BuLi, hexamethylphosphoramide (HMPA), 2.) pTsCl, LiCl / 1.) ether, hexane, 0 deg C, 10 min, 2.) a) 0 deg C, 1 h, b) RT, 2 h

5: 79 percent / Li₂CuCl₄ / tetrahydrofuran / 0.5 h

6: 72 percent / BF₃*OEt₂, Et₃N / CH₂Cl₂; benzene; hexane / 0.75 h / -78 °C

7: 97 percent / oxalyl chloride, DMSO / tetrahydrofuran / -78 - -35 °C

8: 1.) MgBr₂*OEt₂, 2.) L-Selectride / 1.) CH₂Cl₂, -10 deg C, 5 min, 2.) THF, from -78 deg C to RT, 2 h

9: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) THF, -35 deg C, 5 min, 2.) RT, 1 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; oxalyl dichloride; dilithium tetrachlorocuprate; boron trifluoride diethyl etherate; sodium methylate; tetra-(n-butyl)ammonium iodide; L-Selectride; sodium hydride; dimethyl sulfoxide; triethylamine; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; lithium chloride; magnesium bromide; In tetrahydrofuran; methanol; hexane; dichloromethane; benzene;
DOI:10.1021/jo00256a007