methyl (methyl 2aα, 3β, 5β, 5aα, 6α, 8β, 8aα-3, 4, 5, 7, 8-decahydro-5a-methyl-3, 5, 8-trihydroxy-2H-naphtho<4.4a.5.bc>furan-2a-carboxylate-6-)acetate-3,5-benzylidene acetal

Base Information

Chemical Name:methyl (methyl 2aα, 3β, 5β, 5aα, 6α, 8β, 8aα-3, 4, 5, 7, 8-decahydro-5a-methyl-3, 5, 8-trihydroxy-2H-naphtho<4.4a.5.bc>furan-2a-carboxylate-6-)acetate-3,5-benzylidene acetal
CAS No.:125317-96-6
Molecular Formula:C₂₄H₃₀O₈
Molecular Weight:446.497
Hs Code.:

methyl (methyl 2aα, 3β, 5β, 5aα, 6α, 8β, 8aα-3, 4, 5, 7, 8-decahydro-5a-methyl-3, 5, 8-trihydroxy-2H-naphtho<4.4a.5.bc>furan-2a-carboxylate-6-)acetate-3,5-benzylidene acetal

Synonyms:methyl (methyl 2aα, 3β, 5β, 5aα, 6α, 8β, 8aα-3, 4, 5, 7, 8-decahydro-5a-methyl-3, 5, 8-trihydroxy-2H-naphtho<4.4a.5.bc>furan-2a-carboxylate-6-)acetate-3,5-benzylidene acetal

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Chemical Property of methyl (methyl 2aα, 3β, 5β, 5aα, 6α, 8β, 8aα-3, 4, 5, 7, 8-decahydro-5a-methyl-3, 5, 8-trihydroxy-2H-naphtho<4.4a.5.bc>furan-2a-carboxylate-6-)acetate-3,5-benzylidene acetal

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Technology Process of methyl (methyl 2aα, 3β, 5β, 5aα, 6α, 8β, 8aα-3, 4, 5, 7, 8-decahydro-5a-methyl-3, 5, 8-trihydroxy-2H-naphtho<4.4a.5.bc>furan-2a-carboxylate-6-)acetate-3,5-benzylidene acetal

There total 21 articles about methyl (methyl 2aα, 3β, 5β, 5aα, 6α, 8β, 8aα-3, 4, 5, 7, 8-decahydro-5a-methyl-3, 5, 8-trihydroxy-2H-naphtho<4.4a.5.bc>furan-2a-carboxylate-6-)acetate-3,5-benzylidene acetal 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%

: 100-52-7
benzaldehyde

: 125318-04-9,125409-98-5
methyl (methyl 2aα, 3β, 5β, 5aα, 6α, 8β, 8aα-3, 4, 5, 7, 8-decahydro-5a-methyl-3, 5, 8-trihydroxy-2H-naphtho<4.4a.5.bc>furan-2a-carboxylate-6-)acetate

: 125317-96-6
methyl (methyl 2aα, 3β, 5β, 5aα, 6α, 8β, 8aα-3, 4, 5, 7, 8-decahydro-5a-methyl-3, 5, 8-trihydroxy-2H-naphtho<4.4a.5.bc>furan-2a-carboxylate-6-)acetate-3,5-benzylidene acetal

Guidance literature:: With pyridinium p-toluenesulfonate; In benzene; at 80 ℃; for 1.5h; Heating;
DOI:10.1016/S0040-4020(01)80075-2

Reference yield:

: 107368-26-3
(E)-Ethyl 3-methyl-4-oxo-2-pentenoate

: 125317-96-6
methyl (methyl 2aα, 3β, 5β, 5aα, 6α, 8β, 8aα-3, 4, 5, 7, 8-decahydro-5a-methyl-3, 5, 8-trihydroxy-2H-naphtho<4.4a.5.bc>furan-2a-carboxylate-6-)acetate-3,5-benzylidene acetal

Guidance literature:: Multi-step reaction with 21 steps

1: 100 percent / pyridinium para-toluenesulphonate / benzene / 60 h / Heating

2: 98 percent / lithium aluminum hydride / diethyl ether / 0.33 h / -50 - 0 °C

3: 89 percent / manganese(IV) oxide / CHCl₃ / 48 h / Ambient temperature

4: 93 percent / n-buthyl lithium / tetrahydrofuran; hexane / 0.17 h / -92 °C

5: 94 percent / 1.) potassium hydride, TMEDA; 2.) pyridinium para-toluenesulphonate / acetone; H₂O / 5 h / Heating

6: 79 percent / pyridinium para-toluenesulphonate / benzene / 12 h / Heating

7: 87 percent / triethylamine / CH₂Cl₂ / 0.5 h / -20 °C

8: 23 percent / dimethylsulfoxide / 1 h / 135 °C / Heating

9: 73 percent / aq. acetic acid / tetrahydrofuran / 18 h / 65 °C / Heating

10: 90 percent / piperidine, acetic acid / benzene / 15 h / 80 °C / Heating

11: 60 percent / sodium methoxide / methanol / 8.3 h / Ambient temperature

12: 91 percent / sodium chloride / dimethylsulfoxide; H₂O / 4 h / 160 °C

13: 90 percent / diisopropylamine, n-butyl lithium / tetrahydrofuran; hexane / 0.75 h / -78 °C

14: 68 percent / 2-(phenylsulphonyl)-3-p-nitrophenyloxaziridine, aq. sodium hydrogencarbonate / CH₂Cl₂ / 1.5 h / Ambient temperature

15: 70 percent / calcium carbonate / acetonitrile; H₂O / 3 h / Heating

16: 78 percent / cerium trichloride heptahydrate, sodium borohydride / methanol / 0.08 h / Ambient temperature

17: 60 percent / MnO₂ / CH₂Cl₂ / 7 h / Ambient temperature

18: 95 percent / H₂O₂, aq. potassium carbonate / methanol / 1.75 h / 0 °C

19: 95 percent / 10 percent aq. sodium hydrogencarbonate, aluminum amalgam / ethanol / 1.67 h / Ambient temperature

20: 68 percent / solid sodium hydrogencarbonate, magnesium dibromide mono-etherate, NaBH₄ / tetrahydrofuran / 3 h / -78 °C

21: 95 percent / pyridinium p-toluene sulphonate / benzene / 1.5 h / 80 °C / Heating

With piperidine; manganese(IV) oxide; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; cerium(III) chloride; N,N,N,N,-tetramethylethylenediamine; aluminium amalgam; 3-(4-nitrophenyl)-2-(phenylsulfonyl)-1,2-oxaziridine; dihydrogen peroxide; sodium methylate; pyridinium p-toluenesulfonate; potassium hydride; sodium hydrogencarbonate; potassium carbonate; magnesium bromide ethyl etherate; acetic acid; triethylamine; diisopropylamine; calcium carbonate; sodium chloride; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; chloroform; water; dimethyl sulfoxide; acetone; acetonitrile; benzene;
DOI:10.1016/S0040-4020(01)80075-2

Reference yield:

: 121362-86-5
(E)-3-(2-methyl-1,3-dioxolan-2-yl)but-2-enal

: 125317-96-6
methyl (methyl 2aα, 3β, 5β, 5aα, 6α, 8β, 8aα-3, 4, 5, 7, 8-decahydro-5a-methyl-3, 5, 8-trihydroxy-2H-naphtho<4.4a.5.bc>furan-2a-carboxylate-6-)acetate-3,5-benzylidene acetal

Guidance literature:: Multi-step reaction with 18 steps

1: 93 percent / n-buthyl lithium / tetrahydrofuran; hexane / 0.17 h / -92 °C

2: 94 percent / 1.) potassium hydride, TMEDA; 2.) pyridinium para-toluenesulphonate / acetone; H₂O / 5 h / Heating

3: 79 percent / pyridinium para-toluenesulphonate / benzene / 12 h / Heating

4: 87 percent / triethylamine / CH₂Cl₂ / 0.5 h / -20 °C

5: 23 percent / dimethylsulfoxide / 1 h / 135 °C / Heating

6: 73 percent / aq. acetic acid / tetrahydrofuran / 18 h / 65 °C / Heating

7: 90 percent / piperidine, acetic acid / benzene / 15 h / 80 °C / Heating

8: 60 percent / sodium methoxide / methanol / 8.3 h / Ambient temperature

9: 91 percent / sodium chloride / dimethylsulfoxide; H₂O / 4 h / 160 °C

10: 90 percent / diisopropylamine, n-butyl lithium / tetrahydrofuran; hexane / 0.75 h / -78 °C

11: 68 percent / 2-(phenylsulphonyl)-3-p-nitrophenyloxaziridine, aq. sodium hydrogencarbonate / CH₂Cl₂ / 1.5 h / Ambient temperature

12: 70 percent / calcium carbonate / acetonitrile; H₂O / 3 h / Heating

13: 78 percent / cerium trichloride heptahydrate, sodium borohydride / methanol / 0.08 h / Ambient temperature

14: 60 percent / MnO₂ / CH₂Cl₂ / 7 h / Ambient temperature

15: 95 percent / H₂O₂, aq. potassium carbonate / methanol / 1.75 h / 0 °C

16: 95 percent / 10 percent aq. sodium hydrogencarbonate, aluminum amalgam / ethanol / 1.67 h / Ambient temperature

17: 68 percent / solid sodium hydrogencarbonate, magnesium dibromide mono-etherate, NaBH₄ / tetrahydrofuran / 3 h / -78 °C

18: 95 percent / pyridinium p-toluene sulphonate / benzene / 1.5 h / 80 °C / Heating

With piperidine; manganese(IV) oxide; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; N,N,N,N,-tetramethylethylenediamine; aluminium amalgam; 3-(4-nitrophenyl)-2-(phenylsulfonyl)-1,2-oxaziridine; dihydrogen peroxide; sodium methylate; pyridinium p-toluenesulfonate; potassium hydride; sodium hydrogencarbonate; potassium carbonate; magnesium bromide ethyl etherate; acetic acid; triethylamine; diisopropylamine; calcium carbonate; sodium chloride; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; acetone; acetonitrile; benzene;
DOI:10.1016/S0040-4020(01)80075-2