(3aR,6aR)-4-Benzo[1,3]dioxol-5-yl-6-(3,4,5-trimethoxy-phenyl)-tetrahydro-furo[3,4-c]furan-1-one

Base Information

Chemical Name:(3aR,6aR)-4-Benzo[1,3]dioxol-5-yl-6-(3,4,5-trimethoxy-phenyl)-tetrahydro-furo[3,4-c]furan-1-one
CAS No.:108763-77-5
Molecular Formula:C₂₂H₂₂O₈
Molecular Weight:414.412
Hs Code.:

Synonyms:(3aR,6aR)-4-Benzo[1,3]dioxol-5-yl-6-(3,4,5-trimethoxy-phenyl)-tetrahydro-furo[3,4-c]furan-1-one

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Chemical Property of (3aR,6aR)-4-Benzo[1,3]dioxol-5-yl-6-(3,4,5-trimethoxy-phenyl)-tetrahydro-furo[3,4-c]furan-1-one

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Technology Process of (3aR,6aR)-4-Benzo[1,3]dioxol-5-yl-6-(3,4,5-trimethoxy-phenyl)-tetrahydro-furo[3,4-c]furan-1-one

There total 9 articles about (3aR,6aR)-4-Benzo[1,3]dioxol-5-yl-6-(3,4,5-trimethoxy-phenyl)-tetrahydro-furo[3,4-c]furan-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: 19.0%

: 96323-55-6,108815-06-1
(2S,3S)-2-((2R,4S,5S)-4-Benzo[1,3]dioxol-5-yl-2-phenyl-[1,3]dioxan-5-yl)-3-hydroxy-3-(3,4,5-trimethoxy-phenyl)-propionic acid methyl ester

: 108763-77-5
(3aR,6aR)-4-Benzo[1,3]dioxol-5-yl-6-(3,4,5-trimethoxy-phenyl)-tetrahydro-furo[3,4-c]furan-1-one

: 108763-78-6,108815-07-2,108815-08-3
(1S,9S,12S)-8-Benzo[1,3]dioxol-5-yl-4,5,6-trimethoxy-11-oxa-tricyclo[7.2.1.0^2,7]dodeca-2,4,6-triene-12-carboxylic acid methyl ester

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at -20 - 0 ℃;
DOI:10.1016/S0040-4020(01)87655-9

Reference yield:

: 120-57-0,30024-74-9
piperonal

: 108763-77-5
(3aR,6aR)-4-Benzo[1,3]dioxol-5-yl-6-(3,4,5-trimethoxy-phenyl)-tetrahydro-furo[3,4-c]furan-1-one

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) (i.Pr)2NH, n.BuLi / 1.) THF/hexane, -78 deg C, 45 min, 2.) THF/hexane, -78 deg C, 30 min

2: 95 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

3: 70 percent / CuSO₄ / CHCl₃ / 48 h / Ambient temperature

4: 86 percent / CrO_3.Py₂ / CH₂Cl₂ / 0.25 h

5: 78 percent / Ag₂O, NaOH / H₂O; methanol / 4 h / 60 °C

6: 100 percent / diethyl ether / 0 °C

7: 1.) N-isopropylcyclohexylamine, n-BuLi / 1.) hexane/THF, 30 min, -78 deg C; 30 min, -78 - -40 deg C; 30 min, -40 deg C, 2.) hexane?THF, 5 min, -100 deg C

8: 51 percent / TFA / CH₂Cl₂ / -20 - 0 °C

With sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; N-cyclohexylisopropylamine; dipyridine chromium trioxide; copper(II) sulfate; diisopropylamine; trifluoroacetic acid; silver(l) oxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; water;
DOI:10.1016/S0040-4020(01)87655-9

Reference yield:

: 86-81-7
3,4,5-trimethoxy-benzaldehyde

: 108763-77-5
(3aR,6aR)-4-Benzo[1,3]dioxol-5-yl-6-(3,4,5-trimethoxy-phenyl)-tetrahydro-furo[3,4-c]furan-1-one

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) N-isopropylcyclohexylamine, n-BuLi / 1.) hexane/THF, 30 min, -78 deg C; 30 min, -78 - -40 deg C; 30 min, -40 deg C, 2.) hexane?THF, 5 min, -100 deg C

2: 51 percent / TFA / CH₂Cl₂ / -20 - 0 °C

With n-butyllithium; N-cyclohexylisopropylamine; trifluoroacetic acid; In dichloromethane;
DOI:10.1016/S0040-4020(01)87655-9