<2R,4aR,6R(1'S,2'S,3'R),8aS>-4,4a,6,8a-tetrahydro-6-(2-methoxy-1,3-dimethylpent-4-enyl)-7-methyl-2-phenylpyrano<3,2-d>-1,3-dioxin

Base Information

Chemical Name:<2R,4aR,6R(1'S,2'S,3'R),8aS>-4,4a,6,8a-tetrahydro-6-(2-methoxy-1,3-dimethylpent-4-enyl)-7-methyl-2-phenylpyrano<3,2-d>-1,3-dioxin
CAS No.:150019-05-9
Molecular Formula:C₂₂H₃₀O₄
Molecular Weight:358.478
Hs Code.:

Synonyms:<2R,4aR,6R(1'S,2'S,3'R),8aS>-4,4a,6,8a-tetrahydro-6-(2-methoxy-1,3-dimethylpent-4-enyl)-7-methyl-2-phenylpyrano<3,2-d>-1,3-dioxin

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Chemical Property of <2R,4aR,6R(1'S,2'S,3'R),8aS>-4,4a,6,8a-tetrahydro-6-(2-methoxy-1,3-dimethylpent-4-enyl)-7-methyl-2-phenylpyrano<3,2-d>-1,3-dioxin

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Technology Process of <2R,4aR,6R(1'S,2'S,3'R),8aS>-4,4a,6,8a-tetrahydro-6-(2-methoxy-1,3-dimethylpent-4-enyl)-7-methyl-2-phenylpyrano<3,2-d>-1,3-dioxin

There total 7 articles about <2R,4aR,6R(1'S,2'S,3'R),8aS>-4,4a,6,8a-tetrahydro-6-(2-methoxy-1,3-dimethylpent-4-enyl)-7-methyl-2-phenylpyrano<3,2-d>-1,3-dioxin 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:

: 150196-68-2
4,6-O-Benzyliden-1,2-didehydro-1,2-dideoxy-2-methyl-D-ribo-hexopyranose

: 150019-05-9
<2R,4aR,6R(1'S,2'S,3'R),8aS>-4,4a,6,8a-tetrahydro-6-(2-methoxy-1,3-dimethylpent-4-enyl)-7-methyl-2-phenylpyrano<3,2-d>-1,3-dioxin

Guidance literature:: Multi-step reaction with 7 steps

1: 96 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

2: 1.) hexamethyldisilazane, n-BuLi, 2.) HMPA / 1.) THF, -100 deg C, 30 min, 2.) THF, from -100 deg C to RT, 90 min, 3.) benzene, reflux, 19 h

3: 2 N aq. NaOH / tetrahydrofuran / 3 h

4: 87 percent / LiAlH₄ / diethyl ether / 3 h / 0 °C

5: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) CH₂Cl₂, a) -78 deg C, 40 min, b) from -78 deg C to 0 deg C, 2 h

6: 1.) t-BuOK, n-BuLi, 2.) (-)-B-methoxydiisopinocampheylborane, BF₃*OEt₂, 3.) 3 N aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 deg C, 2.5 h, 3.) THF, hexane, reflux, 16 h

7: 1.) NaH / 1.) THF, hexane, RT, 1 h, 2.) THF, hexane, RT, 24 h

With pyridine; (-)-B-methoxydiisopinocamphenylborane; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; boron trifluoride diethyl etherate; potassium tert-butylate; dihydrogen peroxide; sodium hydride; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ja00069a013

Reference yield:

: 2-((2R,4aR,6R,8aS)-7-Methyl-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-propionic acid

: 150019-05-9
<2R,4aR,6R(1'S,2'S,3'R),8aS>-4,4a,6,8a-tetrahydro-6-(2-methoxy-1,3-dimethylpent-4-enyl)-7-methyl-2-phenylpyrano<3,2-d>-1,3-dioxin

Guidance literature:: Multi-step reaction with 4 steps

1: 87 percent / LiAlH₄ / diethyl ether / 3 h / 0 °C

2: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) CH₂Cl₂, a) -78 deg C, 40 min, b) from -78 deg C to 0 deg C, 2 h

3: 1.) t-BuOK, n-BuLi, 2.) (-)-B-methoxydiisopinocampheylborane, BF₃*OEt₂, 3.) 3 N aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 deg C, 2.5 h, 3.) THF, hexane, reflux, 16 h

4: 1.) NaH / 1.) THF, hexane, RT, 1 h, 2.) THF, hexane, RT, 24 h

With (-)-B-methoxydiisopinocamphenylborane; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; boron trifluoride diethyl etherate; potassium tert-butylate; dihydrogen peroxide; sodium hydride; dimethyl sulfoxide; triethylamine; In diethyl ether;
DOI:10.1021/ja00069a013

Reference yield:

: (R)-1,5-anhydro-2-deoxy-2-methyl-4,6-O-(phenylmethylene)-D-ribohex-1-enitol propionate

: 150019-05-9
<2R,4aR,6R(1'S,2'S,3'R),8aS>-4,4a,6,8a-tetrahydro-6-(2-methoxy-1,3-dimethylpent-4-enyl)-7-methyl-2-phenylpyrano<3,2-d>-1,3-dioxin

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) hexamethyldisilazane, n-BuLi, 2.) HMPA / 1.) THF, -100 deg C, 30 min, 2.) THF, from -100 deg C to RT, 90 min, 3.) benzene, reflux, 19 h

2: 2 N aq. NaOH / tetrahydrofuran / 3 h

3: 87 percent / LiAlH₄ / diethyl ether / 3 h / 0 °C

4: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) CH₂Cl₂, a) -78 deg C, 40 min, b) from -78 deg C to 0 deg C, 2 h

5: 1.) t-BuOK, n-BuLi, 2.) (-)-B-methoxydiisopinocampheylborane, BF₃*OEt₂, 3.) 3 N aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 deg C, 2.5 h, 3.) THF, hexane, reflux, 16 h

6: 1.) NaH / 1.) THF, hexane, RT, 1 h, 2.) THF, hexane, RT, 24 h

With (-)-B-methoxydiisopinocamphenylborane; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; boron trifluoride diethyl etherate; potassium tert-butylate; dihydrogen peroxide; sodium hydride; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; diethyl ether;
DOI:10.1021/ja00069a013