(3S,4S)-1,1-dibromo-3-(4-methoxybenzyloxy)-4,5-pentylidenedioxy-1-pentene

Base Information

• Chemical Name: (3S,4S)-1,1-dibromo-3-(4-methoxybenzyloxy)-4,5-pentylidenedioxy-1-pentene
• CAS No.: 198057-20-4
• Molecular Formula: C₁₈H₂₄Br₂O₄
• Molecular Weight: 464.194

Synonyms:

Chemical Property of (3S,4S)-1,1-dibromo-3-(4-methoxybenzyloxy)-4,5-pentylidenedioxy-1-pentene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-1,1-dibromo-3-(4-methoxybenzyloxy)-4,5-pentylidenedioxy-1-pentene

There total 1 articles about (3S,4S)-1,1-dibromo-3-(4-methoxybenzyloxy)-4,5-pentylidenedioxy-1-pentene 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:

carbon tetrabromide (558-13-4) + (R)-((S)-2,2-Diethyl-[1,3]dioxolan-4-yl)-(4-methoxy-benzyloxy)-acetaldehyde (174968-09-3) → (3S,4S)-1,1-dibromo-3-(4-methoxybenzyloxy)-4,5-pentylidenedioxy-1-pentene (198057-20-4)

Guidance literature:

With triphenylphosphine; Yield given. Multistep reaction; 1.) CH₂Cl₂, 0 deg C, 10 min, 2.) CH₂Cl₂, -78 deg C, 20 min;

DOI:10.1248/cpb.45.1558

Reference yield:

(3S,4S)-1,1-dibromo-3-(4-methoxybenzyloxy)-4,5-pentylidenedioxy-1-pentene (198057-20-4) → (2S,3R,4R,5S,6S)-2-Allyl-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-[(R)-2-(4-methoxy-phenyl)-[1,3]dioxolan-4-ylmethyl]-4-methyl-tetrahydro-pyran (198057-17-9)

Guidance literature:

Multi-step reaction with 35 steps

1: 1.) N-BuLi / 1.) n-hexane, THF, -78 deg C, 1 h, 2.) n-hexane, THF, from -78 deg C, 30 min to RT, 1 h

2: 90 percent / H₂, quinoline / 5percent Pd/BaSO₄ / ethyl acetate / 0.25 h

3: 98 percent / 1N aq. HCl / methanol / 2 h / Ambient temperature

4: 96 percent / imidazole / CH₂Cl₂ / 1 h / Ambient temperature

5: 95 percent / TsOH*H₂O / benzene / 17 h / Ambient temperature

6: 1.) DIBAH, 2.) dl-CSA / 1.) n-hexane, toluene, -78 deg C, 1 h, 2.) RT, 30 min

7: 97 percent / DDQ, phosphate buffer / methanol / 1 h / Ambient temperature

8: 74 percent / MCPBA, 4,4'-thiobis(6-tert-butyl-m-cresol) / CH₂Cl₂ / 40 h / Heating

9: 1.) Et₂O, THF, 0 deg C, 1 h, 2.) Et₂O, THF, RT, 3 d

10: 99 percent / Et₃N, DMAP / CH₂Cl₂ / 0.5 h / Ambient temperature

11: 100 percent / TBAF, AcOH / tetrahydrofuran / 5 h / Ambient temperature

12: 96 percent / i-Pr₂NEt / CH₂Cl₂ / 10 h / Ambient temperature

13: 97 percent / K₂CO₃ / methanol / 0.67 h / Ambient temperature

14: 93 percent / 2,6-di-tert-butylpyridine / CH₂Cl₂ / 1 h / Ambient temperature

15: 87 percent / H₂ / 10percent Pd(OH)2/C / ethyl acetate / 7 h / 760 Torr / Ambient temperature

16: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, -40 deg C, 40 min

17: 1.) t-BuOK / 1.) THF, -20 deg C, 30 min, 2.) THF, RT, 40 min

18: 1.) disiamylborane, 2.) 15percent aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, 0 deg C, 7 h, 2.) THF, RT, 10 h

19: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, a) -78 deg C, 30 min, b) -40 deg C, 30 min

20: 1.) t-BuOK / 1.) THF, 0 deg C, 30 min, 2.) THF, 0 deg C, 20 min

21: 97 percent / DIBAH / tetrahydrofuran; CH₂Cl₂ / 4.5 h / -78 °C

22: 91 percent / D-(-)-diethyl tartrate, (i-PrO)4Ti, t-butylhydroperoxide, MS 4 Angstroem / CH₂Cl₂; 2,2,4-trimethyl-pentane / 24 h

23: 98 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / Ambient temperature

24: 97 percent / NaI, NaHCO₃ / butan-2-one / 12 h / 60 °C

25: 94 percent / t-BuLi / toluene; diethyl ether / 1 h / -78 °C

26: 91 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / Ambient temperature

27: OsO₄, N-methylmorpholine N-oxide hydrate, H₂O / 2-methyl-propan-2-ol; acetone / 4 h / Ambient temperature

28: aq. NaIO₄ / tetrahydrofuran / 12 h / Ambient temperature

29: NaBH₄ / tetrahydrofuran / 1 h / Ambient temperature

30: Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

31: 85 percent / BF₃*Et₂O, allyltriemthylsilane / acetonitrile / 0.25 h / Ambient temperature

32: 80 percent / BF₃*Et₂O, TMSOTf / acetonitrile / 3 h / 0 °C

33: Et₃N / CH₂Cl₂ / 0.5 h / Ambient temperature

34: K₂CO₃ / methanol / 0.5 h / Ambient temperature

35: CSA / benzene / 2 h / Ambient temperature

With 1H-imidazole; quinoline; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; sodium hydroxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; Santonox R; n-butyllithium; 2,6-di-tert-butyl-pyridine; phosphate buffer; oxalyl dichloride; diethyl (2S,3S)-tartrate; trimethylsilyl trifluoromethanesulfonate; DL-10-camphorsulfonic acid; MS 4 Angstroem; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; water; hydrogen; dihydrogen peroxide; tert.-butyl lithium; bis-(1,2-dimethylpropyl)borane; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; allyl-trimethyl-silane; palladium dihydroxide; Pd-BaSO₄; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; dichloromethane; ethyl acetate; acetone; toluene; acetonitrile; butanone; tert-butyl alcohol; benzene;

DOI:10.1248/cpb.45.1558

Reference yield:

(3S,4S)-1,1-dibromo-3-(4-methoxybenzyloxy)-4,5-pentylidenedioxy-1-pentene (198057-20-4) → (R)-3-[(2S,3S,4R,5R,6S)-6-Allyl-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-tetrahydro-pyran-2-yl]-2-(4-methoxy-benzyloxy)-propionaldehyde

Guidance literature:

Multi-step reaction with 37 steps

1: 1.) N-BuLi / 1.) n-hexane, THF, -78 deg C, 1 h, 2.) n-hexane, THF, from -78 deg C, 30 min to RT, 1 h

2: 90 percent / H₂, quinoline / 5percent Pd/BaSO₄ / ethyl acetate / 0.25 h

3: 98 percent / 1N aq. HCl / methanol / 2 h / Ambient temperature

4: 96 percent / imidazole / CH₂Cl₂ / 1 h / Ambient temperature

5: 95 percent / TsOH*H₂O / benzene / 17 h / Ambient temperature

6: 1.) DIBAH, 2.) dl-CSA / 1.) n-hexane, toluene, -78 deg C, 1 h, 2.) RT, 30 min

7: 97 percent / DDQ, phosphate buffer / methanol / 1 h / Ambient temperature

8: 74 percent / MCPBA, 4,4'-thiobis(6-tert-butyl-m-cresol) / CH₂Cl₂ / 40 h / Heating

9: 1.) Et₂O, THF, 0 deg C, 1 h, 2.) Et₂O, THF, RT, 3 d

10: 99 percent / Et₃N, DMAP / CH₂Cl₂ / 0.5 h / Ambient temperature

11: 100 percent / TBAF, AcOH / tetrahydrofuran / 5 h / Ambient temperature

12: 96 percent / i-Pr₂NEt / CH₂Cl₂ / 10 h / Ambient temperature

13: 97 percent / K₂CO₃ / methanol / 0.67 h / Ambient temperature

14: 93 percent / 2,6-di-tert-butylpyridine / CH₂Cl₂ / 1 h / Ambient temperature

15: 87 percent / H₂ / 10percent Pd(OH)2/C / ethyl acetate / 7 h / 760 Torr / Ambient temperature

16: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, -40 deg C, 40 min

17: 1.) t-BuOK / 1.) THF, -20 deg C, 30 min, 2.) THF, RT, 40 min

18: 1.) disiamylborane, 2.) 15percent aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, 0 deg C, 7 h, 2.) THF, RT, 10 h

19: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, a) -78 deg C, 30 min, b) -40 deg C, 30 min

20: 1.) t-BuOK / 1.) THF, 0 deg C, 30 min, 2.) THF, 0 deg C, 20 min

21: 97 percent / DIBAH / tetrahydrofuran; CH₂Cl₂ / 4.5 h / -78 °C

22: 91 percent / D-(-)-diethyl tartrate, (i-PrO)4Ti, t-butylhydroperoxide, MS 4 Angstroem / CH₂Cl₂; 2,2,4-trimethyl-pentane / 24 h

23: 98 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / Ambient temperature

24: 97 percent / NaI, NaHCO₃ / butan-2-one / 12 h / 60 °C

25: 94 percent / t-BuLi / toluene; diethyl ether / 1 h / -78 °C

26: 91 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / Ambient temperature

27: OsO₄, N-methylmorpholine N-oxide hydrate, H₂O / 2-methyl-propan-2-ol; acetone / 4 h / Ambient temperature

28: aq. NaIO₄ / tetrahydrofuran / 12 h / Ambient temperature

29: NaBH₄ / tetrahydrofuran / 1 h / Ambient temperature

30: Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

31: 85 percent / BF₃*Et₂O, allyltriemthylsilane / acetonitrile / 0.25 h / Ambient temperature

32: 80 percent / BF₃*Et₂O, TMSOTf / acetonitrile / 3 h / 0 °C

33: Et₃N / CH₂Cl₂ / 0.5 h / Ambient temperature

34: K₂CO₃ / methanol / 0.5 h / Ambient temperature

35: CSA / benzene / 2 h / Ambient temperature

36: 52 percent / DIBAH / hexane; CH₂Cl₂ / 1 h / -78 °C

37: 72 percent / Dess-Martin reagent / CH₂Cl₂ / 0.33 h / Ambient temperature

With 1H-imidazole; quinoline; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; sodium hydroxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; Santonox R; n-butyllithium; 2,6-di-tert-butyl-pyridine; phosphate buffer; oxalyl dichloride; diethyl (2S,3S)-tartrate; trimethylsilyl trifluoromethanesulfonate; DL-10-camphorsulfonic acid; MS 4 Angstroem; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; water; hydrogen; dihydrogen peroxide; tert.-butyl lithium; bis-(1,2-dimethylpropyl)borane; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; allyl-trimethyl-silane; palladium dihydroxide; Pd-BaSO₄; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; ethyl acetate; acetone; toluene; acetonitrile; butanone; tert-butyl alcohol; benzene;

DOI:10.1248/cpb.45.1558

upstream raw materials:

carbon tetrabromide

(R)-((S)-2,2-Diethyl-[1,3]dioxolan-4-yl)-(4-methoxy-benzyloxy)-acetaldehyde

Downstream raw materials:

(2R,3R,4S,5S,6S)-6-benzyloxymethyloxymethyl-3,5-dihydroxy-2-methoxy-4-methyl-3,4,5,6-tetrahydro-2H-pyran

(Z)-(4S,5S)-5,6-Dihydroxy-4-(4-methoxy-benzyloxy)-hex-2-enoic acid methyl ester

(Z)-(S)-4-((S)-2,2-Diethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-but-2-enoic acid methyl ester

(2S,3S,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-3,6-dihydro-2H-pyran-3-ol

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