(3R,5R)-7-<(2S,5R)-5-benzoyloxymethyl-3-(methylidene)tetrahydrofuryl>-5-(4-methoxybenzyloxy)-3-methylheptanenitrile

Base Information

Chemical Name:(3R,5R)-7-<(2S,5R)-5-benzoyloxymethyl-3-(methylidene)tetrahydrofuryl>-5-(4-methoxybenzyloxy)-3-methylheptanenitrile
CAS No.:214533-18-3
Molecular Formula:C₂₉H₃₅NO₅
Molecular Weight:477.601
Hs Code.:

Synonyms:

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Chemical Property of (3R,5R)-7-<(2S,5R)-5-benzoyloxymethyl-3-(methylidene)tetrahydrofuryl>-5-(4-methoxybenzyloxy)-3-methylheptanenitrile

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Technology Process of (3R,5R)-7-<(2S,5R)-5-benzoyloxymethyl-3-(methylidene)tetrahydrofuryl>-5-(4-methoxybenzyloxy)-3-methylheptanenitrile

There total 22 articles about (3R,5R)-7-<(2S,5R)-5-benzoyloxymethyl-3-(methylidene)tetrahydrofuryl>-5-(4-methoxybenzyloxy)-3-methylheptanenitrile 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:

: 186641-79-2
(R)-4-((tert-Butyldiphenylsilyl)oxy)-3-methylbutanal

: 214533-18-3
(3R,5R)-7-<(2S,5R)-5-benzoyloxymethyl-3-(methylidene)tetrahydrofuryl>-5-(4-methoxybenzyloxy)-3-methylheptanenitrile

Guidance literature:: Multi-step reaction with 20 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

With pyridine; titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; diethyl (2R,3R)-tartrate; 3 A molecular sieve; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium iodide; nickel; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; toluene; benzene;
DOI:10.1248/cpb.46.1199

Reference yield:

: 186641-76-9
(2R)-1-(tert-butyldiphenylsilyloxy)-3-cyano-2-methylpropane

: 214533-18-3
(3R,5R)-7-<(2S,5R)-5-benzoyloxymethyl-3-(methylidene)tetrahydrofuryl>-5-(4-methoxybenzyloxy)-3-methylheptanenitrile

Guidance literature:: Multi-step reaction with 21 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

With pyridine; titanium(IV) isopropylate; hydrogenchloride; methanol; tert.-butylhydroperoxide; dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; diethyl (2R,3R)-tartrate; 3 A molecular sieve; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; rochelle salt; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium iodide; nickel; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; toluene; benzene;
DOI:10.1248/cpb.46.1199

Reference yield:

: 157240-43-2
(4R)-4,5-isopropylidenedioxy-1-(dimethoxyphosphoryl)-2-pentanone

: 214533-18-3
(3R,5R)-7-<(2S,5R)-5-benzoyloxymethyl-3-(methylidene)tetrahydrofuryl>-5-(4-methoxybenzyloxy)-3-methylheptanenitrile

Guidance literature:: Multi-step reaction with 13 steps

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

2: 97 percent / LiAlH₄, LiI / diethyl ether / 1 h / -100 °C

3: 96 percent / AcOH, MeOH / 24 h / Ambient temperature

4: 86 percent / NaHCO₃, I₂ / tetrahydrofuran / 0.5 h / 0 °C

5: 60 percent / NaH / tetrahydrofuran / 1 h / Ambient temperature

6: 90 percent / H₂ / Raney-Ni / ethanol / 760 Torr / Ambient temperature

7: 84 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

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

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

10: Et₃N, DMAP / CH₂Cl₂ / 1 h / 0 °C

11: 86 percent / TBAF / tetrahydrofuran / 3 h / Ambient temperature

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

13: dimethylsulfoxide / 0.5 h / 50 °C

With pyridine; methanol; dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium hydride; sodium hydrogencarbonate; acetic acid; dimethyl sulfoxide; triethylamine; lithium iodide; nickel; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1248/cpb.46.1199