(2R,3S,4R,5S,6S,8S,10R,11R,12R,13R)-3,5-<(p-bromobenzylidene)dioxy>-8,8-(epoxymethano)-11-hydroxy-2,4,6,10,12,13-hexamethyl-9-oxotetradecanolide

Base Information

Chemical Name:(2R,3S,4R,5S,6S,8S,10R,11R,12R,13R)-3,5-<(p-bromobenzylidene)dioxy>-8,8-(epoxymethano)-11-hydroxy-2,4,6,10,12,13-hexamethyl-9-oxotetradecanolide
CAS No.:156766-85-7
Molecular Formula:C₂₇H₃₇BrO₇
Molecular Weight:553.491
Hs Code.:

Synonyms:(2R,3S,4R,5S,6S,8S,10R,11R,12R,13R)-3,5-<(p-bromobenzylidene)dioxy>-8,8-(epoxymethano)-11-hydroxy-2,4,6,10,12,13-hexamethyl-9-oxotetradecanolide

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Chemical Property of (2R,3S,4R,5S,6S,8S,10R,11R,12R,13R)-3,5-<(p-bromobenzylidene)dioxy>-8,8-(epoxymethano)-11-hydroxy-2,4,6,10,12,13-hexamethyl-9-oxotetradecanolide

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Technology Process of (2R,3S,4R,5S,6S,8S,10R,11R,12R,13R)-3,5-<(p-bromobenzylidene)dioxy>-8,8-(epoxymethano)-11-hydroxy-2,4,6,10,12,13-hexamethyl-9-oxotetradecanolide

There total 31 articles about (2R,3S,4R,5S,6S,8S,10R,11R,12R,13R)-3,5-<(p-bromobenzylidene)dioxy>-8,8-(epoxymethano)-11-hydroxy-2,4,6,10,12,13-hexamethyl-9-oxotetradecanolide 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: 89.0%

: 156766-84-6
(2R,3S,4R,5S,6S,8S,9R,10R,11R,12R,13R)-3,5-<(p-bromobenzylidene)dioxy>-8,8-(epoxymethano)-9,11-dihydroxy-2,4,6,10,12,13-hexamethyltetradecanolide

: 156766-85-7
(2R,3S,4R,5S,6S,8S,10R,11R,12R,13R)-3,5-<(p-bromobenzylidene)dioxy>-8,8-(epoxymethano)-11-hydroxy-2,4,6,10,12,13-hexamethyl-9-oxotetradecanolide

Guidance literature:: With aluminum oxide; pyridinium chlorochromate; In toluene;
DOI:10.1021/ja00087a068

Reference yield:

: 116546-78-2
(S)-1-benzyloxy-2-methylpentan-3-one

: 156766-85-7
(2R,3S,4R,5S,6S,8S,10R,11R,12R,13R)-3,5-<(p-bromobenzylidene)dioxy>-8,8-(epoxymethano)-11-hydroxy-2,4,6,10,12,13-hexamethyl-9-oxotetradecanolide

Guidance literature:: Multi-step reaction with 19 steps

1: 1.) (cyclohexyl)2BCl, Et₃N, 3.) 30percent aq. H₂O₂, pH 7 buffer

2: 92 percent / Me₄NHB(OAc)3, AcOH / acetonitrile / 50.5 h / -30 - -20 °C

3: 93 percent / p-TsOH / CH₂Cl₂ / 70 h

4: 97 percent / LiDBB / tetrahydrofuran / 0.5 h / -78 °C

5: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, from -78 to -23 deg C, 30 min

6: CH₂Cl₂; tetrahydrofuran / 0.25 h / -100 °C

7: 1.) KH / 1.) THF, 5 min, 2.) THF, from 0 to 20 deg C, 1.5 h

8: 1.) aq. OsO₄, N-methylmorpholine N-oxide, 2.) NaIO₄, pH 7 buffer / 1.) t-BuOH, THF, 20 deg C, 15 h, 2.) t-BuOH, THF, 20 deg C, 25 min

9: 1.) LiNEt₂ / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 deg C, 30 min

10: 1.) Raney nickel, 2.) H₂ / 2.) Raney nickel / 1.) Et₂O, EtOH, RT, 3 h, 2.) Et₂O, EtOH, overnight

11: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CHCl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, from -78 to -23 deg C, 45 min

12: aq. NaClO₄, NaH₂PO₄, 2-methyl-2-butene, / 2-methyl-propan-2-ol / 0.5 h / Ambient temperature

13: 97 percent / H₂ / 10percent Pd/C / ethanol / 18 h

14: Et₃N / tetrahydrofuran / 2.5 h

15: Et₃N, DMAP / toluene; tetrahydrofuran / 0.5 h / 60 °C

16: 1.) KHMDS / 1.) toluene, 60 deg C, 30 min, 2.) toluene, reflux, 1 h

17: 94 percent / aq. HCl / tetrahydrofuran / 2 h / 50 °C

18: 1.) CSA, 2.) aq. NaHCO₃ / 1.) CH₂Cl₂, RT, 1 h, 2.) CH₂Cl₂, RT, 20 min

19: 78 percent / PCC/alumina / toluene / 18 h / Ambient temperature

With hydrogenchloride; dmap; aluminum oxide; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; 2-methyl-but-2-ene; oxalyl dichloride; lithium 4,4′-di(tert-butyl)biphenyl; pH 7 buffer; camphor-10-sulfonic acid; dicyclohexylboron chloride; lithium diethylamide; sodium perchlorate; hydrogen; dihydrogen peroxide; potassium hydride; potassium hexamethylsilazane; nickel; sodium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; pyridinium chlorochromate; tetramethylammonium triacetoxyborohydride; palladium on activated charcoal; nickel; In tetrahydrofuran; ethanol; dichloromethane; toluene; acetonitrile; tert-butyl alcohol;
DOI:10.1021/ja00104a010

Reference yield:

: 128146-35-0,128241-48-5
(2S,3S,4S,5S,6E)-1-(benzyloxy)-2,4-dimethyl-6-octene-3,5-diol

: 156766-85-7
(2R,3S,4R,5S,6S,8S,10R,11R,12R,13R)-3,5-<(p-bromobenzylidene)dioxy>-8,8-(epoxymethano)-11-hydroxy-2,4,6,10,12,13-hexamethyl-9-oxotetradecanolide

Guidance literature:: Multi-step reaction with 17 steps

1: 93 percent / p-TsOH / CH₂Cl₂ / 70 h

2: 97 percent / LiDBB / tetrahydrofuran / 0.5 h / -78 °C

3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, from -78 to -23 deg C, 30 min

4: CH₂Cl₂; tetrahydrofuran / 0.25 h / -100 °C

5: 1.) KH / 1.) THF, 5 min, 2.) THF, from 0 to 20 deg C, 1.5 h

6: 1.) aq. OsO₄, N-methylmorpholine N-oxide, 2.) NaIO₄, pH 7 buffer / 1.) t-BuOH, THF, 20 deg C, 15 h, 2.) t-BuOH, THF, 20 deg C, 25 min

7: 1.) LiNEt₂ / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 deg C, 30 min

8: 1.) Raney nickel, 2.) H₂ / 2.) Raney nickel / 1.) Et₂O, EtOH, RT, 3 h, 2.) Et₂O, EtOH, overnight

9: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CHCl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, from -78 to -23 deg C, 45 min

10: aq. NaClO₄, NaH₂PO₄, 2-methyl-2-butene, / 2-methyl-propan-2-ol / 0.5 h / Ambient temperature

11: 97 percent / H₂ / 10percent Pd/C / ethanol / 18 h

12: Et₃N / tetrahydrofuran / 2.5 h

13: Et₃N, DMAP / toluene; tetrahydrofuran / 0.5 h / 60 °C

14: 1.) KHMDS / 1.) toluene, 60 deg C, 30 min, 2.) toluene, reflux, 1 h

15: 94 percent / aq. HCl / tetrahydrofuran / 2 h / 50 °C

16: 1.) CSA, 2.) aq. NaHCO₃ / 1.) CH₂Cl₂, RT, 1 h, 2.) CH₂Cl₂, RT, 20 min

17: 78 percent / PCC/alumina / toluene / 18 h / Ambient temperature

With hydrogenchloride; dmap; aluminum oxide; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; 2-methyl-but-2-ene; oxalyl dichloride; lithium 4,4′-di(tert-butyl)biphenyl; pH 7 buffer; camphor-10-sulfonic acid; lithium diethylamide; sodium perchlorate; hydrogen; potassium hydride; potassium hexamethylsilazane; nickel; sodium hydrogencarbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; pyridinium chlorochromate; palladium on activated charcoal; nickel; In tetrahydrofuran; ethanol; dichloromethane; toluene; tert-butyl alcohol;
DOI:10.1021/ja00104a010