(S)-3-{(2R,13R)-13-Benzyloxymethoxy-2,8-bis-methoxymethoxy-13-[(2S,5S)-5-((S)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-tridecyl}-5-methyl-5H-furan-2-one

Base Information

Chemical Name:(S)-3-{(2R,13R)-13-Benzyloxymethoxy-2,8-bis-methoxymethoxy-13-[(2S,5S)-5-((S)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-tridecyl}-5-methyl-5H-furan-2-one
CAS No.:201472-24-4
Molecular Formula:C₄₉H₈₄O₁₁
Molecular Weight:849.199
Hs Code.:

(S)-3-{(2R,13R)-13-Benzyloxymethoxy-2,8-bis-methoxymethoxy-13-[(2S,5S)-5-((S)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-tridecyl}-5-methyl-5H-furan-2-one

Synonyms:(S)-3-{(2R,13R)-13-Benzyloxymethoxy-2,8-bis-methoxymethoxy-13-[(2S,5S)-5-((S)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-tridecyl}-5-methyl-5H-furan-2-one

Suppliers and Price of (S)-3-{(2R,13R)-13-Benzyloxymethoxy-2,8-bis-methoxymethoxy-13-[(2S,5S)-5-((S)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-tridecyl}-5-methyl-5H-furan-2-one

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of (S)-3-{(2R,13R)-13-Benzyloxymethoxy-2,8-bis-methoxymethoxy-13-[(2S,5S)-5-((S)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-tridecyl}-5-methyl-5H-furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (S)-3-{(2R,13R)-13-Benzyloxymethoxy-2,8-bis-methoxymethoxy-13-[(2S,5S)-5-((S)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-tridecyl}-5-methyl-5H-furan-2-one

There total 31 articles about (S)-3-{(2R,13R)-13-Benzyloxymethoxy-2,8-bis-methoxymethoxy-13-[(2S,5S)-5-((S)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-tridecyl}-5-methyl-5H-furan-2-one 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

: 201472-24-4
(S)-3-{(2R,13R)-13-Benzyloxymethoxy-2,8-bis-methoxymethoxy-13-[(2S,5S)-5-((S)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-tridecyl}-5-methyl-5H-furan-2-one

Guidance literature:: Multi-step reaction with 20 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

19: 97 percent / NiCl₂*6H₂O, NaBH₄ / methanol / 0.08 h / 0 °C

20: 1.) n-BuLi, DIPEA, 3.) CSA, 4.) TEA, MsCl, 5.) DBU / 1) THF, hexane, -78 deg C, 30 min; 2) THF, hexane, -78 deg C, 25 min; 3) methanol, water, rt, 4 h; 4) CH₂Cl₂, 0 deg C --> rt, 2 h; 5) CH₂Cl₂, 0 deg C, 30 min

With dmap; sodium tetrahydroborate; disodium hydrogenphosphate; lithium aluminium tetrahydride; n-butyllithium; tetrapropylammonium perruthennate; sodium amalgam; oxalyl dichloride; 4 A molecular sieve; TEA; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen; acetic anhydride; L-Selectride; diisobutylaluminium hydride; dimethyl sulfoxide; methanesulfonyl chloride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; benzoic acid; nickel dichloride; 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

: 201472-24-4
(S)-3-{(2R,13R)-13-Benzyloxymethoxy-2,8-bis-methoxymethoxy-13-[(2S,5S)-5-((S)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-tridecyl}-5-methyl-5H-furan-2-one

Guidance literature:: Multi-step reaction with 21 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

20: 97 percent / NiCl₂*6H₂O, NaBH₄ / methanol / 0.08 h / 0 °C

21: 1.) n-BuLi, DIPEA, 3.) CSA, 4.) TEA, MsCl, 5.) DBU / 1) THF, hexane, -78 deg C, 30 min; 2) THF, hexane, -78 deg C, 25 min; 3) methanol, water, rt, 4 h; 4) CH₂Cl₂, 0 deg C --> rt, 2 h; 5) CH₂Cl₂, 0 deg C, 30 min

With dmap; sodium tetrahydroborate; disodium hydrogenphosphate; lithium aluminium tetrahydride; n-butyllithium; tetrapropylammonium perruthennate; sodium amalgam; oxalyl dichloride; 4 A molecular sieve; TEA; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen; acetic anhydride; L-Selectride; diisobutylaluminium hydride; dimethyl sulfoxide; methanesulfonyl chloride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; benzoic acid; nickel dichloride; 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

: 201472-24-4
(S)-3-{(2R,13R)-13-Benzyloxymethoxy-2,8-bis-methoxymethoxy-13-[(2S,5S)-5-((S)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-tridecyl}-5-methyl-5H-furan-2-one

Guidance literature:: Multi-step reaction with 19 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

18: 97 percent / NiCl₂*6H₂O, NaBH₄ / methanol / 0.08 h / 0 °C

19: 1.) n-BuLi, DIPEA, 3.) CSA, 4.) TEA, MsCl, 5.) DBU / 1) THF, hexane, -78 deg C, 30 min; 2) THF, hexane, -78 deg C, 25 min; 3) methanol, water, rt, 4 h; 4) CH₂Cl₂, 0 deg C --> rt, 2 h; 5) CH₂Cl₂, 0 deg C, 30 min

With lithium hydroxide; sodium tetrahydroborate; disodium hydrogenphosphate; lithium aluminium tetrahydride; n-butyllithium; tetrapropylammonium perruthennate; sodium amalgam; oxalyl dichloride; 4 A molecular sieve; TEA; camphor-10-sulfonic acid; hydrogen; L-Selectride; diisobutylaluminium hydride; dimethyl sulfoxide; methanesulfonyl chloride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; triphenylphosphine; benzoic acid; nickel dichloride; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene;
DOI:10.1021/jo9713621