(3aR,7S,7aR)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

Base Information

Chemical Name:(3aR,7S,7aR)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester
CAS No.:160017-25-4
Molecular Formula:C₁₉H₂₄O₆
Molecular Weight:348.396
Hs Code.:

Synonyms:(3aR,7S,7aR)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

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Chemical Property of (3aR,7S,7aR)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

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Technology Process of (3aR,7S,7aR)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

There total 1 articles about (3aR,7S,7aR)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl 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:

Reference yield: 95.0%

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 160080-76-2
(3aR,7S,7aS)-7-Hydroxy-2,2-dimethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

: 160017-25-4
(3aR,7S,7aR)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

Guidance literature:: With trityl tetrafluoroborate; In diethyl ether; at 0 ℃; for 1h;
DOI:10.1016/S0040-4039(00)73491-5

Reference yield:

: 160017-25-4
(3aR,7S,7aR)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

: (5Z,8Z,14Z)-(10S,11S,12R)-11-Hydroxy-10-(4-methoxy-benzyloxy)-12-(toluene-4-sulfonyloxy)-icosa-5,8,14-trienoic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) OsO₄, NMO; 2.) Pb(OAc)4, Na₂CO₃; 3.) LiAlH₄ / 1.) acetone/water, 23 deg C, 4 h; 2.) CH₂Cl₂, -78 deg C, 0.25 h; 3.) THF, 23 deg C, 3 h

2: Pb(OAc)4, Na₂CO₃ / CH₂Cl₂ / 0.25 h / -78 °C

3: tetrahydrofuran / - 78 deg C, 0.5 h, 23 deg C, 12 h

4: 1.) (COCl)2/DMSO; 2.) Et₃N / CH₂Cl₂ / 1.) -78 deg C, 1 h; 2.) -78 to 23 deg C, 0.3 h

5: tetrahydrofuran; toluene / -78 deg C, 0.1 h; -40 deg C, 1 h; 0 deg C, 0.5 h

6: 99 percent / 0.5percent HCl / methanol / 12 h / 23 °C

7: 87 percent / DMAP/Et₃N / CH₂Cl₂ / 48 h / -28 °C

With lead(IV) acetate; hydrogenchloride; dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; oxalyl dichloride; sodium carbonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; toluene;
DOI:10.1016/S0040-4039(00)73491-5

Reference yield:

: 160017-25-4
(3aR,7S,7aR)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

: 173522-75-3
Benzoic acid (2Z,5Z)-(R)-9-methoxycarbonyl-1-[(2S,3R)-((Z)-3-oct-2-enyl)-oxiranyl]-nona-2,5-dienyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) OsO₄, NMO; 2.) Pb(OAc)4, Na₂CO₃; 3.) LiAlH₄ / 1.) acetone/water, 23 deg C, 4 h; 2.) CH₂Cl₂, -78 deg C, 0.25 h; 3.) THF, 23 deg C, 3 h

2: Pb(OAc)4, Na₂CO₃ / CH₂Cl₂ / 0.25 h / -78 °C

3: tetrahydrofuran / - 78 deg C, 0.5 h, 23 deg C, 12 h

4: 1.) (COCl)2/DMSO; 2.) Et₃N / CH₂Cl₂ / 1.) -78 deg C, 1 h; 2.) -78 to 23 deg C, 0.3 h

5: tetrahydrofuran; toluene / -78 deg C, 0.1 h; -40 deg C, 1 h; 0 deg C, 0.5 h

6: 99 percent / 0.5percent HCl / methanol / 12 h / 23 °C

7: 92 percent / AgNO₃, pyridine / tetrahydrofuran / 96 h / -28 °C

8: Et₃N / CH₂Cl₂ / 0.5 h / -20 °C

9: Bu₄NF / tetrahydrofuran / 1 h / 23 °C

10: DDQ / CH₂Cl₂; H₂O / 3 h / 23 °C

11: DEAD/Ph₃P / benzene / 2 h / 23 °C

With pyridine; lead(IV) acetate; hydrogenchloride; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium carbonate; silver nitrate; dimethyl sulfoxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; toluene; benzene;
DOI:10.1016/S0040-4039(00)73491-5