methyl 2β-<(E)-3-hydroxy-1-methylprop-1-enyl>-7α-acetoxy-5α-(benzyloxy)-4-bromo-1α,6α,8β-trimethyl-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene-1β-carboxylate

Base Information

Chemical Name:methyl 2β-<(E)-3-hydroxy-1-methylprop-1-enyl>-7α-acetoxy-5α-(benzyloxy)-4-bromo-1α,6α,8β-trimethyl-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene-1β-carboxylate
CAS No.:120040-85-9
Molecular Formula:C₂₈H₃₇BrO₆
Molecular Weight:549.502
Hs Code.:

methyl 2β-<(E)-3-hydroxy-1-methylprop-1-enyl>-7α-acetoxy-5α-(benzyloxy)-4-bromo-1α,6α,8β-trimethyl-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene-1β-carboxylate

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

There total 14 articles about methyl 2β-<(E)-3-hydroxy-1-methylprop-1-enyl>-7α-acetoxy-5α-(benzyloxy)-4-bromo-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: 77.0%

: 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

: 120040-85-9
methyl 2β-<(E)-3-hydroxy-1-methylprop-1-enyl>-7α-acetoxy-5α-(benzyloxy)-4-bromo-1α,6α,8β-trimethyl-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene-1β-carboxylate

Guidance literature:: In toluene; at 145 ℃; for 17h;
DOI:10.1016/0040-4039(88)85287-0

Reference yield:

: 120040-82-6,146608-29-9
methyl (E)-(4S,5R,6S,7S)-5-acetoxy-7-(benzyloxy)-9,9-dibromo-2,4,6-trimethylnona-2,8-dienoate

: 120040-85-9
methyl 2β-<(E)-3-hydroxy-1-methylprop-1-enyl>-7α-acetoxy-5α-(benzyloxy)-4-bromo-1α,6α,8β-trimethyl-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene-1β-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 84 percent / 10percent aq. TlOH, Pd(PPh₃)4 / tetrahydrofuran / 0.08 h / 25 °C

2: 77 percent / BHT / toluene / 16 h / 145 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; TlOH; 2,6-di-tert-butyl-4-methyl-phenol; In tetrahydrofuran; toluene;
DOI:10.1021/ja00059a024

Reference yield:

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

: 120040-85-9
methyl 2β-<(E)-3-hydroxy-1-methylprop-1-enyl>-7α-acetoxy-5α-(benzyloxy)-4-bromo-1α,6α,8β-trimethyl-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene-1β-carboxylate

Guidance literature:: Multi-step reaction with 10 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: 85 percent / 4 Angstroem molecular sieves, Ph₃P / CH₂Cl₂ / 0.5 h

9: 84 percent / 10percent aq. TlOH, Pd(PPh₃)4 / tetrahydrofuran / 0.08 h / 25 °C

10: 77 percent / BHT / toluene / 16 h / 145 °C

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