(E)-(4R,15R)-15-Benzyloxymethoxy-4,10-bis-methoxymethoxy-15-[(2S,5S)-5-((S)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-pentadec-2-enoic acid methyl ester

Base Information

Chemical Name:(E)-(4R,15R)-15-Benzyloxymethoxy-4,10-bis-methoxymethoxy-15-[(2S,5S)-5-((S)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-pentadec-2-enoic acid methyl ester
CAS No.:201472-38-0
Molecular Formula:C₄₇H₈₂O₁₁
Molecular Weight:823.161
Hs Code.:

(E)-(4R,15R)-15-Benzyloxymethoxy-4,10-bis-methoxymethoxy-15-[(2S,5S)-5-((S)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-pentadec-2-enoic acid methyl ester

Synonyms:(E)-(4R,15R)-15-Benzyloxymethoxy-4,10-bis-methoxymethoxy-15-[(2S,5S)-5-((S)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-pentadec-2-enoic acid methyl ester

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Chemical Property of (E)-(4R,15R)-15-Benzyloxymethoxy-4,10-bis-methoxymethoxy-15-[(2S,5S)-5-((S)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-pentadec-2-enoic acid methyl ester

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Technology Process of (E)-(4R,15R)-15-Benzyloxymethoxy-4,10-bis-methoxymethoxy-15-[(2S,5S)-5-((S)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-pentadec-2-enoic acid methyl ester

There total 28 articles about (E)-(4R,15R)-15-Benzyloxymethoxy-4,10-bis-methoxymethoxy-15-[(2S,5S)-5-((S)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-pentadec-2-enoic acid methyl 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:

: 201472-26-6
(2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-2-ol

: 201472-38-0
(E)-(4R,15R)-15-Benzyloxymethoxy-4,10-bis-methoxymethoxy-15-[(2S,5S)-5-((S)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-pentadec-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 18 steps

1: 1.) Ac₂O, DMAP, TEA, 2.) BF₃*OEt₂ / 1) CH₂Cl₂, rt, 1 h; 2) CH₂Cl₂, -78 deg C, 1 h

2: 92 percent / H₂ / Pd/C / ethyl acetate / 5 h / 760 Torr

3: 94 percent / DIBAL-H / toluene / 1 h / -78 °C

4: 85 percent / PhCO₂H / CH₂Cl₂ / 12 h / Ambient temperature

5: 1.5 g / H₂ / Pd/C / ethyl acetate / 5 h / Ambient temperature

6: 65 percent / DIPEA / CH₂Cl₂ / 48 h / 0 °C

7: 0.5 g / n-BuNF / tetrahydrofuran / 3 h / Ambient temperature

8: 1.) oxalyl chloride, DMSO, 2.) DIPEA / 1) THF, -78 to -35 deg C, 15 min; 2) THF, ether, 0 deg C

9: TPAP, N-methylmorpholine N-oxide, 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / Ambient temperature

10: 105 mg / L-selectride / tetrahydrofuran / 1 h / -78 °C

11: 88 percent / DIPEA / CH₂Cl₂ / 12 h / 4 °C

12: 1.) n-BuLi / 1) THF, hexane, 0 deg C, 15 min; 2) THF, hexane, -40 to 0 deg C, 1 h

13: 94 percent / Na₂HPO₄, Na-Hg amalgam / methanol / 3 h / 0 °C

14: 84 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

15: 100 percent / DIPEA / CH₂Cl₂ / 4 h / 4 °C

16: 95 percent / n-BuNF / tetrahydrofuran / 3 h / Ambient temperature

17: TPAP, N-methylmorpholine N-oxide, 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / Ambient temperature

18: CH₂Cl₂ / 5 h / Ambient temperature

With dmap; disodium hydrogenphosphate; lithium aluminium tetrahydride; n-butyllithium; tetrapropylammonium perruthennate; sodium amalgam; oxalyl dichloride; 4 A molecular sieve; TEA; boron trifluoride diethyl etherate; hydrogen; acetic anhydride; L-Selectride; diisobutylaluminium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; benzoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene;
DOI:10.1021/jo9713621

Reference yield:

: 102717-29-3
(5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one

: 201472-38-0
(E)-(4R,15R)-15-Benzyloxymethoxy-4,10-bis-methoxymethoxy-15-[(2S,5S)-5-((S)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-pentadec-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 19 steps

1: 92 percent / DIBAL-H / toluene / 1 h / -78 °C

2: 1.) Ac₂O, DMAP, TEA, 2.) BF₃*OEt₂ / 1) CH₂Cl₂, rt, 1 h; 2) CH₂Cl₂, -78 deg C, 1 h

3: 92 percent / H₂ / Pd/C / ethyl acetate / 5 h / 760 Torr

4: 94 percent / DIBAL-H / toluene / 1 h / -78 °C

5: 85 percent / PhCO₂H / CH₂Cl₂ / 12 h / Ambient temperature

6: 1.5 g / H₂ / Pd/C / ethyl acetate / 5 h / Ambient temperature

7: 65 percent / DIPEA / CH₂Cl₂ / 48 h / 0 °C

8: 0.5 g / n-BuNF / tetrahydrofuran / 3 h / Ambient temperature

9: 1.) oxalyl chloride, DMSO, 2.) DIPEA / 1) THF, -78 to -35 deg C, 15 min; 2) THF, ether, 0 deg C

10: TPAP, N-methylmorpholine N-oxide, 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / Ambient temperature

11: 105 mg / L-selectride / tetrahydrofuran / 1 h / -78 °C

12: 88 percent / DIPEA / CH₂Cl₂ / 12 h / 4 °C

13: 1.) n-BuLi / 1) THF, hexane, 0 deg C, 15 min; 2) THF, hexane, -40 to 0 deg C, 1 h

14: 94 percent / Na₂HPO₄, Na-Hg amalgam / methanol / 3 h / 0 °C

15: 84 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

16: 100 percent / DIPEA / CH₂Cl₂ / 4 h / 4 °C

17: 95 percent / n-BuNF / tetrahydrofuran / 3 h / Ambient temperature

18: TPAP, N-methylmorpholine N-oxide, 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / Ambient temperature

19: CH₂Cl₂ / 5 h / Ambient temperature

With dmap; disodium hydrogenphosphate; lithium aluminium tetrahydride; n-butyllithium; tetrapropylammonium perruthennate; sodium amalgam; oxalyl dichloride; 4 A molecular sieve; TEA; boron trifluoride diethyl etherate; hydrogen; acetic anhydride; L-Selectride; diisobutylaluminium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; benzoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene;
DOI:10.1021/jo9713621

Reference yield:

: 157810-24-7
(2S,2'S,5'S)-5'-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-[2,2']bifuranyl-5-one

: 201472-38-0
(E)-(4R,15R)-15-Benzyloxymethoxy-4,10-bis-methoxymethoxy-15-[(2S,5S)-5-((S)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-pentadec-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 17 steps

1: 1.) LiOH, 2.) Ph₃P, DEAD / 1) THF, H₂O, 0 deg C, 1 h; 2) THF, 0 deg C, 30 min

2: 94 percent / DIBAL-H / toluene / 1 h / -78 °C

3: 85 percent / PhCO₂H / CH₂Cl₂ / 12 h / Ambient temperature

4: 1.5 g / H₂ / Pd/C / ethyl acetate / 5 h / Ambient temperature

5: 65 percent / DIPEA / CH₂Cl₂ / 48 h / 0 °C

6: 0.5 g / n-BuNF / tetrahydrofuran / 3 h / Ambient temperature

7: 1.) oxalyl chloride, DMSO, 2.) DIPEA / 1) THF, -78 to -35 deg C, 15 min; 2) THF, ether, 0 deg C

8: TPAP, N-methylmorpholine N-oxide, 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / Ambient temperature

9: 105 mg / L-selectride / tetrahydrofuran / 1 h / -78 °C

10: 88 percent / DIPEA / CH₂Cl₂ / 12 h / 4 °C

11: 1.) n-BuLi / 1) THF, hexane, 0 deg C, 15 min; 2) THF, hexane, -40 to 0 deg C, 1 h

12: 94 percent / Na₂HPO₄, Na-Hg amalgam / methanol / 3 h / 0 °C

13: 84 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

14: 100 percent / DIPEA / CH₂Cl₂ / 4 h / 4 °C

15: 95 percent / n-BuNF / tetrahydrofuran / 3 h / Ambient temperature

16: TPAP, N-methylmorpholine N-oxide, 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / Ambient temperature

17: CH₂Cl₂ / 5 h / Ambient temperature

With lithium hydroxide; disodium hydrogenphosphate; lithium aluminium tetrahydride; n-butyllithium; tetrapropylammonium perruthennate; sodium amalgam; oxalyl dichloride; 4 A molecular sieve; hydrogen; L-Selectride; diisobutylaluminium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; benzoic acid; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene;
DOI:10.1021/jo9713621