Technology Process of (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 (S)-O-methylmandelate ester
There total 14 articles about (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 (S)-O-methylmandelate ester 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:
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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
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116078-12-7
(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 (S)-O-methylmandelate ester
- Guidance literature:
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With
dmap; dicyclohexyl-carbodiimide;
In
dichloromethane;
for 24h;
Ambient temperature;
DOI:10.1021/jo00256a007
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116078-12-7
(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 (S)-O-methylmandelate ester
- Guidance literature:
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Multi-step reaction with 8 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: 1,3-dicyclohexylcarbodiimide, DMAP / CH2Cl2 / 24 h / Ambient temperature
With
N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; n-butyllithium; dilithium tetrachlorocuprate; boron trifluoride diethyl etherate; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; lithium chloride;
In
tetrahydrofuran; methanol; hexane; dichloromethane; benzene;
DOI:10.1021/jo00256a007
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116078-12-7
(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 (S)-O-methylmandelate ester
- Guidance literature:
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Multi-step reaction with 7 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: 1,3-dicyclohexylcarbodiimide, DMAP / CH2Cl2 / 24 h / Ambient temperature
With
N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; n-butyllithium; dilithium tetrachlorocuprate; boron trifluoride diethyl etherate; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; lithium chloride;
In
tetrahydrofuran; methanol; hexane; dichloromethane; benzene;
DOI:10.1021/jo00256a007
