methyl (3R,5S)-7-<(2S,5R)-3-methylidene-5-(2-(trimethylsilyl)ethoxymethoxymethyl)tetrahydrofuryl>-5-(4-methoxybenzyloxy)-5-methylheptanoate

Base Information

Chemical Name:methyl (3R,5S)-7-<(2S,5R)-3-methylidene-5-(2-(trimethylsilyl)ethoxymethoxymethyl)tetrahydrofuryl>-5-(4-methoxybenzyloxy)-5-methylheptanoate
CAS No.:157158-48-0
Molecular Formula:C₂₉H₄₈O₇Si
Molecular Weight:536.781
Hs Code.:

Synonyms:methyl (3R,5S)-7-<(2S,5R)-3-methylidene-5-(2-(trimethylsilyl)ethoxymethoxymethyl)tetrahydrofuryl>-5-(4-methoxybenzyloxy)-5-methylheptanoate

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Chemical Property of methyl (3R,5S)-7-<(2S,5R)-3-methylidene-5-(2-(trimethylsilyl)ethoxymethoxymethyl)tetrahydrofuryl>-5-(4-methoxybenzyloxy)-5-methylheptanoate

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Technology Process of methyl (3R,5S)-7-<(2S,5R)-3-methylidene-5-(2-(trimethylsilyl)ethoxymethoxymethyl)tetrahydrofuryl>-5-(4-methoxybenzyloxy)-5-methylheptanoate

There total 27 articles about methyl (3R,5S)-7-<(2S,5R)-3-methylidene-5-(2-(trimethylsilyl)ethoxymethoxymethyl)tetrahydrofuryl>-5-(4-methoxybenzyloxy)-5-methylheptanoate 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

: 157158-48-0
methyl (3R,5S)-7-<(2S,5R)-3-methylidene-5-(2-(trimethylsilyl)ethoxymethoxymethyl)tetrahydrofuryl>-5-(4-methoxybenzyloxy)-5-methylheptanoate

Guidance literature:: Multi-step reaction with 25 steps

1: CH₂Cl₂ / 10 h / Ambient temperature

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

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

4: 93 percent / sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran / 30 h / -20 °C

5: 100 percent / p-TsOH*H₂O / benzene / 3 h / Ambient temperature

6: 90 percent / 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: 99 percent / LiAlH₄, LiI / diethyl ether / 1 h / -100 °C

10: 89 percent / AcOH, MeOH / 24 h / Ambient temperature

11: 88 percent / NaHCO₃, I₂ / tetrahydrofuran / 0.5 h / 0 °C

12: 90 percent / NaH / tetrahydrofuran / 1 h / Ambient temperature

13: 100 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: 88 percent / TBAF / tetrahydrofuran / 3 h / Ambient temperature

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

20: dimethylsulfoxide / 0.5 h / 50 °C

21: 99 percent / K₂CO₃ / methanol / 4 h / Ambient temperature

22: 97 percent / (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

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

Reference yield:

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

: 157158-48-0
methyl (3R,5S)-7-<(2S,5R)-3-methylidene-5-(2-(trimethylsilyl)ethoxymethoxymethyl)tetrahydrofuryl>-5-(4-methoxybenzyloxy)-5-methylheptanoate

Guidance literature:: Multi-step reaction with 26 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, D-(-)-DET, 3A molecular sieves, tert-butylhydroperoxide / CH₂Cl₂; toluene / 8 h / Ambient temperature

5: 93 percent / sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran / 30 h / -20 °C

6: 100 percent / p-TsOH*H₂O / benzene / 3 h / Ambient temperature

7: 90 percent / 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: 99 percent / LiAlH₄, LiI / diethyl ether / 1 h / -100 °C

11: 89 percent / AcOH, MeOH / 24 h / Ambient temperature

12: 88 percent / NaHCO₃, I₂ / tetrahydrofuran / 0.5 h / 0 °C

13: 90 percent / NaH / tetrahydrofuran / 1 h / Ambient temperature

14: 100 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: 88 percent / TBAF / tetrahydrofuran / 3 h / Ambient temperature

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

21: dimethylsulfoxide / 0.5 h / 50 °C

22: 99 percent / K₂CO₃ / methanol / 4 h / Ambient temperature

23: 97 percent / (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

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

Reference yield:

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

: 157158-48-0
methyl (3R,5S)-7-<(2S,5R)-3-methylidene-5-(2-(trimethylsilyl)ethoxymethoxymethyl)tetrahydrofuryl>-5-(4-methoxybenzyloxy)-5-methylheptanoate

Guidance literature:: Multi-step reaction with 18 steps

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

2: 99 percent / LiAlH₄, LiI / diethyl ether / 1 h / -100 °C

3: 89 percent / AcOH, MeOH / 24 h / Ambient temperature

4: 88 percent / NaHCO₃, I₂ / tetrahydrofuran / 0.5 h / 0 °C

5: 90 percent / NaH / tetrahydrofuran / 1 h / Ambient temperature

6: 100 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: 88 percent / TBAF / tetrahydrofuran / 3 h / Ambient temperature

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

13: dimethylsulfoxide / 0.5 h / 50 °C

14: 99 percent / K₂CO₃ / methanol / 4 h / Ambient temperature

15: 97 percent / (iso-Pr)2EtN / CH₂Cl₂ / 2 h / Ambient temperature

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

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

18: diethyl ether

With pyridine; chromium(VI) oxide; methanol; dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; sulfuric acid; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; dimethyl sulfoxide; rochelle salt; triethylamine; N-ethyl-N,N-diisopropylamine; lithium iodide; nickel; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; acetone;
DOI:10.1248/cpb.46.1199