benzoic acid 5-(2-{6-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-4-methyl-tetrahydro-pyran-2-ylmethyl]-4-methyl-5-methylene-tetrahydro-pyran-2-yl}-ethyl)-4-methylene-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: benzoic acid 5-(2-{6-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-4-methyl-tetrahydro-pyran-2-ylmethyl]-4-methyl-5-methylene-tetrahydro-pyran-2-yl}-ethyl)-4-methylene-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 214533-33-2
• Molecular Formula: C₄₇H₇₈O₉Si₂
• Molecular Weight: 843.302
• Mol file: 214533-33-2.mol

Synonyms:benzoic acid 5-(2-{6-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-4-methyl-tetrahydro-pyran-2-ylmethyl]-4-methyl-5-methylene-tetrahydro-pyran-2-yl}-ethyl)-4-methylene-tetrahydro-furan-2-ylmethyl ester

Chemical Property of benzoic acid 5-(2-{6-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-4-methyl-tetrahydro-pyran-2-ylmethyl]-4-methyl-5-methylene-tetrahydro-pyran-2-yl}-ethyl)-4-methylene-tetrahydro-furan-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzoic acid 5-(2-{6-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-4-methyl-tetrahydro-pyran-2-ylmethyl]-4-methyl-5-methylene-tetrahydro-pyran-2-yl}-ethyl)-4-methylene-tetrahydro-furan-2-ylmethyl ester

There total 75 articles about benzoic acid 5-(2-{6-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-4-methyl-tetrahydro-pyran-2-ylmethyl]-4-methyl-5-methylene-tetrahydro-pyran-2-yl}-ethyl)-4-methylene-tetrahydro-furan-2-ylmethyl ester 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: 91.0%

t-butyldimethylsiyl triflate (69739-34-0) + (2R,4S,5S,6R,7R,8S,10R,12R,14S,17S,20R)-21-benzoyloxy-1,2-isopropylidenedioxy-6-methyl-11,18-dimethylidene-4,8; 10,14; 17,20-triepoxyhenicosane-5,7-diol (214532-97-5) → benzoic acid 5-(2-{6-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-4-methyl-tetrahydro-pyran-2-ylmethyl]-4-methyl-5-methylene-tetrahydro-pyran-2-yl}-ethyl)-4-methylene-tetrahydro-furan-2-ylmethyl ester (214533-33-2)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1248/cpb.46.1199

Reference yield:

(R)-4-((tert-Butyldiphenylsilyl)oxy)-3-methylbutanal (186641-79-2) → benzoic acid 5-(2-{6-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-4-methyl-tetrahydro-pyran-2-ylmethyl]-4-methyl-5-methylene-tetrahydro-pyran-2-yl}-ethyl)-4-methylene-tetrahydro-furan-2-ylmethyl ester (214533-33-2)

Guidance literature:

Multi-step reaction with 39 steps

1: CH₂Cl₂ / 10 h / Ambient temperature

2: 100 percent / DIBAH / CH₂Cl₂ / 1.5 h / -78 °C

3: 90 percent / (iso-PrO)4Ti, L-(+)-DET, 3A molecular sieves, tert-butylhydroperoxide / CH₂Cl₂; toluene / 8 h / Ambient temperature

4: 98 percent / sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran / 30 h / -20 °C

5: p-TsOH*H₂O / benzene / 3 h / Ambient temperature

6: DIBAH / CH₂Cl₂ / 1.5 h / -78 °C

7: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, -30 deg C, 1 h

8: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, RT, 1 h

9: 97 percent / LiAlH₄, LiI / diethyl ether / 1 h / -100 °C

10: 96 percent / AcOH, MeOH / 24 h / Ambient temperature

11: 86 percent / NaHCO₃, I₂ / tetrahydrofuran / 0.5 h / 0 °C

12: 60 percent / NaH / tetrahydrofuran / 1 h / Ambient temperature

13: 90 percent / H₂ / Raney-Ni / ethanol / 760 Torr / Ambient temperature

14: 84 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

15: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, -78 deg C, 1 h

16: 1.) tert-BuOK / 1.) THF, RT, 1 h, 2.) THF, 0 deg C, 2 h

17: Et₃N, DMAP / CH₂Cl₂ / 1 h / 0 °C

18: 86 percent / TBAF / tetrahydrofuran / 3 h / Ambient temperature

19: Et₃N, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

20: dimethylsulfoxide / 0.5 h / 50 °C

21: K₂CO₃ / methanol / 4 h / Ambient temperature

22: (iso-Pr)2EtN / CH₂Cl₂ / 2 h / Ambient temperature

23: 1.) DIBAH, 2.) aq. Rochelle salt / 1.) CH₂Cl₂, hexane, -78 deg C, 30 min, 2.) CH₂Cl₂, hexane, RT, 3 h

24: CrO₃, H₂SO₄ / acetone / 0.5 h / 20 °C

25: diethyl ether

26: 1.) LDA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 deg C, 15 min

27: 82 percent / LiAlH₄ / tetrahydrofuran / 4 h / 0 °C

28: 90 percent / pyridine / 10 h / Ambient temperature

29: 75 percent / NaI, NaHCO₃, DBU / tetrahydrofuran / 8 h / Heating

30: 78 percent / Dess-Martin reagent / CH₂Cl₂ / 20 h / Ambient temperature

31: 64 percent / LiAlH₄, LiI / diethyl ether / 1 h / -100 °C

32: 96 percent / CH₂Cl₂ / 0.5 h / Ambient temperature

33: 75 percent / DDQ, H₂O / CH₂Cl₂ / 0.5 h / Ambient temperature

34: 90 percent / Et₃N / CH₂Cl₂ / 15 h / Ambient temperature

35: 90 percent / PPTS, MeOH / tetrahydrofuran / 0.5 h / Ambient temperature

36: 69 percent / KH / 1,2-dimethoxy-ethane / 0.5 h / 80 °C

37: TBAF, HMPA / tetrahydrofuran / 5 h / 60 °C

38: pyridine / 0.25 h / 0 °C

39: 91 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

With pyridine; 2,6-dimethylpyridine; chromium(VI) oxide; titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; diethyl (2R,3R)-tartrate; 3 A molecular sieve; sulfuric acid; potassium tert-butylate; tetrabutyl ammonium fluoride; water; hydrogen; iodine; pyridinium p-toluenesulfonate; potassium hydride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; rochelle salt; triethylamine; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; lithium iodide; lithium diisopropyl amide; nickel; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; acetone; toluene; benzene;

DOI:10.1248/cpb.46.1199

Reference yield:

(2R)-1-(tert-butyldiphenylsilyloxy)-3-cyano-2-methylpropane (186641-76-9) → benzoic acid 5-(2-{6-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-4-methyl-tetrahydro-pyran-2-ylmethyl]-4-methyl-5-methylene-tetrahydro-pyran-2-yl}-ethyl)-4-methylene-tetrahydro-furan-2-ylmethyl ester (214533-33-2)

Guidance literature:

Multi-step reaction with 40 steps

1: 1.) DIBAH, 2.) aq. HCl, Rochelle salt / 1.) CH₂Cl₂, THF, -78 deg C, 40 min, 2.) CH₂Cl₂, THF, Et₂O, RT, 12 h

2: CH₂Cl₂ / 10 h / Ambient temperature

3: 100 percent / DIBAH / CH₂Cl₂ / 1.5 h / -78 °C

4: 90 percent / (iso-PrO)4Ti, L-(+)-DET, 3A molecular sieves, tert-butylhydroperoxide / CH₂Cl₂; toluene / 8 h / Ambient temperature

5: 98 percent / sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran / 30 h / -20 °C

6: p-TsOH*H₂O / benzene / 3 h / Ambient temperature

7: DIBAH / CH₂Cl₂ / 1.5 h / -78 °C

8: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, -30 deg C, 1 h

9: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, RT, 1 h

10: 97 percent / LiAlH₄, LiI / diethyl ether / 1 h / -100 °C

11: 96 percent / AcOH, MeOH / 24 h / Ambient temperature

12: 86 percent / NaHCO₃, I₂ / tetrahydrofuran / 0.5 h / 0 °C

13: 60 percent / NaH / tetrahydrofuran / 1 h / Ambient temperature

14: 90 percent / H₂ / Raney-Ni / ethanol / 760 Torr / Ambient temperature

15: 84 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

16: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, -78 deg C, 1 h

17: 1.) tert-BuOK / 1.) THF, RT, 1 h, 2.) THF, 0 deg C, 2 h

18: Et₃N, DMAP / CH₂Cl₂ / 1 h / 0 °C

19: 86 percent / TBAF / tetrahydrofuran / 3 h / Ambient temperature

20: Et₃N, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

21: dimethylsulfoxide / 0.5 h / 50 °C

22: K₂CO₃ / methanol / 4 h / Ambient temperature

23: (iso-Pr)2EtN / CH₂Cl₂ / 2 h / Ambient temperature

24: 1.) DIBAH, 2.) aq. Rochelle salt / 1.) CH₂Cl₂, hexane, -78 deg C, 30 min, 2.) CH₂Cl₂, hexane, RT, 3 h

25: CrO₃, H₂SO₄ / acetone / 0.5 h / 20 °C

26: diethyl ether

27: 1.) LDA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 deg C, 15 min

28: 82 percent / LiAlH₄ / tetrahydrofuran / 4 h / 0 °C

29: 90 percent / pyridine / 10 h / Ambient temperature

30: 75 percent / NaI, NaHCO₃, DBU / tetrahydrofuran / 8 h / Heating

31: 78 percent / Dess-Martin reagent / CH₂Cl₂ / 20 h / Ambient temperature

32: 64 percent / LiAlH₄, LiI / diethyl ether / 1 h / -100 °C

33: 96 percent / CH₂Cl₂ / 0.5 h / Ambient temperature

34: 75 percent / DDQ, H₂O / CH₂Cl₂ / 0.5 h / Ambient temperature

35: 90 percent / Et₃N / CH₂Cl₂ / 15 h / Ambient temperature

36: 90 percent / PPTS, MeOH / tetrahydrofuran / 0.5 h / Ambient temperature

37: 69 percent / KH / 1,2-dimethoxy-ethane / 0.5 h / 80 °C

38: TBAF, HMPA / tetrahydrofuran / 5 h / 60 °C

39: pyridine / 0.25 h / 0 °C

40: 91 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

With pyridine; 2,6-dimethylpyridine; chromium(VI) oxide; titanium(IV) isopropylate; hydrogenchloride; methanol; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; diethyl (2R,3R)-tartrate; 3 A molecular sieve; sulfuric acid; potassium tert-butylate; tetrabutyl ammonium fluoride; water; hydrogen; iodine; pyridinium p-toluenesulfonate; potassium hydride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; rochelle salt; triethylamine; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; lithium iodide; lithium diisopropyl amide; nickel; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; acetone; toluene; benzene;

DOI:10.1248/cpb.46.1199

upstream raw materials:

t-butyldimethylsiyl triflate

(2R,4S,5S,6R,7R,8S,10R,12R,14S,17S,20R)-21-benzoyloxy-1,2-isopropylidenedioxy-6-methyl-11,18-dimethylidene-4,8; 10,14; 17,20-triepoxyhenicosane-5,7-diol

(R)-4-((tert-Butyldiphenylsilyl)oxy)-3-methylbutanal

(2R)-1-(tert-butyldiphenylsilyloxy)-3-cyano-2-methylpropane

Refernces