(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

Base Information

• Chemical Name: (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
• CAS No.: 156766-84-6
• Molecular Formula: C₂₇H₃₉BrO₇
• Molecular Weight: 555.506
• Mol file: 156766-84-6.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 30 articles about (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 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:

(S)-1-benzyloxy-2-methylpentan-3-one (116546-78-2) → (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 (156766-84-6)

Guidance literature:

Multi-step reaction with 18 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

With hydrogenchloride; dmap; 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; tetramethylammonium triacetoxyborohydride; palladium on activated charcoal; nickel; In tetrahydrofuran; ethanol; dichloromethane; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1021/ja00104a010

Reference yield:

(2S,3S,4S,5S,6E)-1-(benzyloxy)-2,4-dimethyl-6-octene-3,5-diol (128146-35-0,128241-48-5) → (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 (156766-84-6)

Guidance literature:

Multi-step reaction with 16 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

With hydrogenchloride; dmap; 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; palladium on activated charcoal; nickel; In tetrahydrofuran; ethanol; dichloromethane; toluene; tert-butyl alcohol;

DOI:10.1021/ja00104a010

Reference yield:

(2S,4S,5S,6E)-1-(benzyloxy)-5-hydroxy-2,4-dimethyl-6-octen-3-one (116546-79-3,116661-38-2,128241-46-3,141611-63-4) → (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 (156766-84-6)

Guidance literature:

Multi-step reaction with 17 steps

1: 92 percent / Me₄NHB(OAc)3, AcOH / acetonitrile / 50.5 h / -30 - -20 °C

2: 93 percent / p-TsOH / CH₂Cl₂ / 70 h

3: 97 percent / LiDBB / tetrahydrofuran / 0.5 h / -78 °C

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

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

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

7: 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

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

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

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

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

12: 97 percent / H₂ / 10percent Pd/C / ethanol / 18 h

13: Et₃N / tetrahydrofuran / 2.5 h

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

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

16: 94 percent / aq. HCl / tetrahydrofuran / 2 h / 50 °C

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

With hydrogenchloride; dmap; 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; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; tetramethylammonium triacetoxyborohydride; palladium on activated charcoal; nickel; In tetrahydrofuran; ethanol; dichloromethane; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1021/ja00104a010

upstream raw materials:

1,1-dimethoxy-1-(4-bromophenyl)methane

(2R,3S,4R,5S,6S,9R,10R,11R,12R,13R)-3,5,9,11-tetrahydroxy-2,4,6,10,12,13-hexamethyl-8-methylenetetradecanolide

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

(S)-1-benzyloxy-2-methylpentan-3-one

Downstream raw materials:

(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