methyl 2β-<(E)-1-methyl-3-<(tert-butyldimethylsilyl)oxy>-prop-1-enyl>-5α-(benzyloxy)-7α-hydroxy-1α,6α,8β-trimethyl-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene-1β-carboxylate

Base Information

Chemical Name:methyl 2β-<(E)-1-methyl-3-<(tert-butyldimethylsilyl)oxy>-prop-1-enyl>-5α-(benzyloxy)-7α-hydroxy-1α,6α,8β-trimethyl-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene-1β-carboxylate
CAS No.:120040-87-1
Molecular Formula:C₃₂H₅₀O₅Si
Molecular Weight:542.832
Hs Code.:

methyl 2β-<(E)-1-methyl-3-<(tert-butyldimethylsilyl)oxy>-prop-1-enyl>-5α-(benzyloxy)-7α-hydroxy-1α,6α,8β-trimethyl-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene-1β-carboxylate

Synonyms:methyl 2β-<(E)-1-methyl-3-<(tert-butyldimethylsilyl)oxy>-prop-1-enyl>-5α-(benzyloxy)-7α-hydroxy-1α,6α,8β-trimethyl-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene-1β-carboxylate

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Chemical Property of methyl 2β-<(E)-1-methyl-3-<(tert-butyldimethylsilyl)oxy>-prop-1-enyl>-5α-(benzyloxy)-7α-hydroxy-1α,6α,8β-trimethyl-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene-1β-carboxylate

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Technology Process of methyl 2β-<(E)-1-methyl-3-<(tert-butyldimethylsilyl)oxy>-prop-1-enyl>-5α-(benzyloxy)-7α-hydroxy-1α,6α,8β-trimethyl-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene-1β-carboxylate

There total 20 articles about methyl 2β-<(E)-1-methyl-3-<(tert-butyldimethylsilyl)oxy>-prop-1-enyl>-5α-(benzyloxy)-7α-hydroxy-1α,6α,8β-trimethyl-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene-1β-carboxylate 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:

: 120040-77-9
(2R,3S)-3-Benzyloxy-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propionaldehyde

: 120040-87-1
methyl 2β-<(E)-1-methyl-3-<(tert-butyldimethylsilyl)oxy>-prop-1-enyl>-5α-(benzyloxy)-7α-hydroxy-1α,6α,8β-trimethyl-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene-1β-carboxylate

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) 4 Angstroem molecular sieves, 3.) NaBH₄

2: 1.) O₃, 2.) Ph₃P / 1.) MeOH, -78 deg C, 2.) MeOH, RT, 2 h

3: 88 percent / toluene; CH₂Cl₂ / 12 h / 45 °C

4: 95 percent / DMAP, Et₃N / CH₂Cl₂ / 16 h

5: 98 percent / aq. AcOH / methanol / 25 h / 95 °C

6: NaIO₄ / tetrahydrofuran; H₂O / 4 h / 25 °C

7: CrCl₂ / tetrahydrofuran / 3 h / 0 °C

8: 76 percent / 10percent TlOH, Pd(PPh₃)4 / methanol; tetrahydrofuran / 0.07 h / 25 °C

9: 64 percent / BHT / toluene / 16 h / 150 °C

10: K₂CO₃ / methanol / Ambient temperature

11: 81 percent / imidazole / dimethylformamide / 1 h / 25 °C

With 1H-imidazole; chromium dichloride; dmap; sodium tetrahydroborate; sodium periodate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; TlOH; 2,6-di-tert-butyl-4-methyl-phenol; 4 A molecular sieve; potassium carbonate; ozone; acetic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja00059a024

Reference yield:

: 120143-05-7
(3S,4S,5S)-4-(benzyloxy)-5,6-(isopropylidenedioxy)-3-methylhex-1-ene

: 120040-87-1
methyl 2β-<(E)-1-methyl-3-<(tert-butyldimethylsilyl)oxy>-prop-1-enyl>-5α-(benzyloxy)-7α-hydroxy-1α,6α,8β-trimethyl-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene-1β-carboxylate

Guidance literature:: Multi-step reaction with 12 steps

1: 1.) O₃, 2.) Me₂S / 1.) MeOH, -78 deg C, 30 min, 2.) MeOH, RT

2: 1.) 4 Angstroem molecular sieves, 3.) NaBH₄

3: 1.) O₃, 2.) Ph₃P / 1.) MeOH, -78 deg C, 2.) MeOH, RT, 2 h

4: 88 percent / toluene; CH₂Cl₂ / 12 h / 45 °C

5: 95 percent / DMAP, Et₃N / CH₂Cl₂ / 16 h

6: 98 percent / aq. AcOH / methanol / 25 h / 95 °C

7: NaIO₄ / tetrahydrofuran; H₂O / 4 h / 25 °C

8: CrCl₂ / tetrahydrofuran / 3 h / 0 °C

9: 76 percent / 10percent TlOH, Pd(PPh₃)4 / methanol; tetrahydrofuran / 0.07 h / 25 °C

10: 64 percent / BHT / toluene / 16 h / 150 °C

11: K₂CO₃ / methanol / Ambient temperature

12: 81 percent / imidazole / dimethylformamide / 1 h / 25 °C

With 1H-imidazole; chromium dichloride; dmap; sodium tetrahydroborate; sodium periodate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; TlOH; dimethylsulfide; 2,6-di-tert-butyl-4-methyl-phenol; 4 A molecular sieve; potassium carbonate; ozone; acetic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja00059a024

Reference yield:

: 120040-84-8,146566-81-6
methyl (E,Z,E,E)-(4S,5R,6S,7S)-5-acetoxy-7-(benzyloxy)-9-bromo-14-hydroxy-2,4,6,12-tetramethyltetradeca-2,8,10,12-tetraenoate

: 120040-87-1
methyl 2β-<(E)-1-methyl-3-<(tert-butyldimethylsilyl)oxy>-prop-1-enyl>-5α-(benzyloxy)-7α-hydroxy-1α,6α,8β-trimethyl-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene-1β-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 77 percent / BHT / toluene / 16 h / 145 °C

2: 1.) Na(Hg), 2.) K₂CO₃ / 1.) MeOH, 25 deg C, 16 h, 2.) MeOH, 1 h

3: 81 percent / imidazole / dimethylformamide / 1 h / 25 °C

With 1H-imidazole; sodium amalgam; 2,6-di-tert-butyl-4-methyl-phenol; potassium carbonate; In N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja00059a024