(3aR,4aS,8aS,9S,9aS)-8-(4-Methoxy-benzyloxymethyl)-9-methoxymethoxy-2,2-dimethyl-4a,5,6,8a,9,9a-hexahydro-3aH-naphtho[2,3-d][1,3]dioxol-4-one

Base Information

Chemical Name:(3aR,4aS,8aS,9S,9aS)-8-(4-Methoxy-benzyloxymethyl)-9-methoxymethoxy-2,2-dimethyl-4a,5,6,8a,9,9a-hexahydro-3aH-naphtho[2,3-d][1,3]dioxol-4-one
CAS No.:198779-26-9
Molecular Formula:C₂₄H₃₂O₇
Molecular Weight:432.514
Hs Code.:

Synonyms:(3aR,4aS,8aS,9S,9aS)-8-(4-Methoxy-benzyloxymethyl)-9-methoxymethoxy-2,2-dimethyl-4a,5,6,8a,9,9a-hexahydro-3aH-naphtho[2,3-d][1,3]dioxol-4-one

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Chemical Property of (3aR,4aS,8aS,9S,9aS)-8-(4-Methoxy-benzyloxymethyl)-9-methoxymethoxy-2,2-dimethyl-4a,5,6,8a,9,9a-hexahydro-3aH-naphtho[2,3-d][1,3]dioxol-4-one

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Technology Process of (3aR,4aS,8aS,9S,9aS)-8-(4-Methoxy-benzyloxymethyl)-9-methoxymethoxy-2,2-dimethyl-4a,5,6,8a,9,9a-hexahydro-3aH-naphtho[2,3-d][1,3]dioxol-4-one

There total 7 articles about (3aR,4aS,8aS,9S,9aS)-8-(4-Methoxy-benzyloxymethyl)-9-methoxymethoxy-2,2-dimethyl-4a,5,6,8a,9,9a-hexahydro-3aH-naphtho[2,3-d][1,3]dioxol-4-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: 75.0%

: 198779-21-4
1-{(4S,5S)-5-[(Z)-(S)-3-(4-Methoxy-benzyloxymethyl)-1-methoxymethoxy-penta-2,4-dienyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-prop-2-en-1-ol

: 198779-26-9
(3aR,4aS,8aS,9S,9aS)-8-(4-Methoxy-benzyloxymethyl)-9-methoxymethoxy-2,2-dimethyl-4a,5,6,8a,9,9a-hexahydro-3aH-naphtho[2,3-d][1,3]dioxol-4-one

Guidance literature:: In dichloromethane; at 48 ℃; for 4h; Dess-Martin periodinane;
DOI:10.1016/S0040-4039(97)01708-5

Reference yield:

: 108817-97-6
(4R,5S)-5-tert-butyldimethylsilyloxymethyl-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

: 198779-26-9
(3aR,4aS,8aS,9S,9aS)-8-(4-Methoxy-benzyloxymethyl)-9-methoxymethoxy-2,2-dimethyl-4a,5,6,8a,9,9a-hexahydro-3aH-naphtho[2,3-d][1,3]dioxol-4-one

Guidance literature:: Multi-step reaction with 6 steps

1: s-BuLi / tetrahydrofuran / -78 °C

2: 77 percent / iPr₂EtN / CH₂Cl₂

3: 94 percent / nBu₄NF / tetrahydrofuran

4: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 40 min, 2) CH₂Cl₂, -78 to 0 deg C

5: 97 percent / tetrahydrofuran / -78 °C

6: 75 percent / CH₂Cl₂ / 4 h / 48 °C / Dess-Martin periodinane

With oxalyl dichloride; tetrabutyl ammonium fluoride; sec.-butyllithium; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4039(97)01708-5

Reference yield:

: 175348-37-5
(Z)-1-iodo-2-(p-methoxybenzyloxy)methyl-1,3-butadiene

: 198779-26-9
(3aR,4aS,8aS,9S,9aS)-8-(4-Methoxy-benzyloxymethyl)-9-methoxymethoxy-2,2-dimethyl-4a,5,6,8a,9,9a-hexahydro-3aH-naphtho[2,3-d][1,3]dioxol-4-one

Guidance literature:: Multi-step reaction with 6 steps

1: s-BuLi / tetrahydrofuran / -78 °C

2: 77 percent / iPr₂EtN / CH₂Cl₂

3: 94 percent / nBu₄NF / tetrahydrofuran

4: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 40 min, 2) CH₂Cl₂, -78 to 0 deg C

5: 97 percent / tetrahydrofuran / -78 °C

6: 75 percent / CH₂Cl₂ / 4 h / 48 °C / Dess-Martin periodinane

With oxalyl dichloride; tetrabutyl ammonium fluoride; sec.-butyllithium; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4039(97)01708-5