6-{(3S,4S,5S,7S)-7-[(2R,3R,5R)-5-Ethyl-5-((2S,5S,6R)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-4-hydroxy-3,5-dimethyl-6-oxo-nonyl}-2-hydroxy-3-methyl-benzoic acid benzyl ester

Base Information

Chemical Name:6-{(3S,4S,5S,7S)-7-[(2R,3R,5R)-5-Ethyl-5-((2S,5S,6R)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-4-hydroxy-3,5-dimethyl-6-oxo-nonyl}-2-hydroxy-3-methyl-benzoic acid benzyl ester
CAS No.:87678-47-5
Molecular Formula:C₄₁H₆₀O₈
Molecular Weight:680.923
Hs Code.:

6-{(3S,4S,5S,7S)-7-[(2R,3R,5R)-5-Ethyl-5-((2S,5S,6R)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-4-hydroxy-3,5-dimethyl-6-oxo-nonyl}-2-hydroxy-3-methyl-benzoic acid benzyl ester

Synonyms:6-{(3S,4S,5S,7S)-7-[(2R,3R,5R)-5-Ethyl-5-((2S,5S,6R)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-4-hydroxy-3,5-dimethyl-6-oxo-nonyl}-2-hydroxy-3-methyl-benzoic acid benzyl ester

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Chemical Property of 6-{(3S,4S,5S,7S)-7-[(2R,3R,5R)-5-Ethyl-5-((2S,5S,6R)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-4-hydroxy-3,5-dimethyl-6-oxo-nonyl}-2-hydroxy-3-methyl-benzoic acid benzyl ester

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Technology Process of 6-{(3S,4S,5S,7S)-7-[(2R,3R,5R)-5-Ethyl-5-((2S,5S,6R)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-4-hydroxy-3,5-dimethyl-6-oxo-nonyl}-2-hydroxy-3-methyl-benzoic acid benzyl ester

There total 19 articles about 6-{(3S,4S,5S,7S)-7-[(2R,3R,5R)-5-Ethyl-5-((2S,5S,6R)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-4-hydroxy-3,5-dimethyl-6-oxo-nonyl}-2-hydroxy-3-methyl-benzoic acid benzyl 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:

: 87678-32-8
benzyl 2(R)-<5(R)-formyl-3(R)-methyl-5-<5(R)-(methoxymethoxy)-6(R)-methyl-2(S)-tetrahydropyranyl>-2(R)-tetrahydrofuryl>butyl ether

: 87678-47-5
6-{(3S,4S,5S,7S)-7-[(2R,3R,5R)-5-Ethyl-5-((2S,5S,6R)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-4-hydroxy-3,5-dimethyl-6-oxo-nonyl}-2-hydroxy-3-methyl-benzoic acid benzyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, then room temp., 1 h, 2.) THF, -78 deg C, then room temp., 10 h

2: 97 percent / H₂ / W-2 Raney nickel catalyst / ethyl acetate / 12 h

3: 10percent aq. HCl / tetrahydrofuran / 12 h / 50 °C

4: 99 percent / oxalyl chloride, dimethyl sulfoxide, triethylamine / CH₂Cl₂ / 0.25 h / -60 °C

5: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, then room temp., 1 h, 2.) THF, -78 deg C, then room temp., 10 h

6: solid NaHCO₃, 80-90percent m-chloroperbenzoic acid / CH₂Cl₂ / 1.) 0 deg C, 2.) room temp., 3 h

7: 1.) cupric bromide-dimethyl sulfide complex / 1.) pentane, ether, 0 deg C, 30 min, 2.) pentane, 2 h

8: 97 percent / lithium wire, anhydrous ammonia / tetrahydrofuran / 1 h

9: oxalyl chloride, dimethyl sulfoxide, triethylamine / CH₂Cl₂ / 2 h / -60 °C

10: 87 percent / oxalyl chloride, dimethyl sulfoxide, triethylamine / CH₂Cl₂ / 2 h / -60 °C

With hydrogenchloride; n-butyllithium; oxalyl dichloride; copper bromide dimethyl sulfide complex; ammonia; hydrogen; lithium; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; W-2 Raney nickel catalyst; In tetrahydrofuran; dichloromethane; ethyl acetate;
DOI:10.1021/jo00174a008

Reference yield:

: 87678-33-9
benzyl 2(R)-<5(S)-vinyl-3(R)-methyl-5-<5(R)-(methoxymethoxy)-6(R)-methyl-2(S)-tetrahydropyranyl>-2(R)-tetrahydrofuryl>butyl ether

: 87678-47-5
6-{(3S,4S,5S,7S)-7-[(2R,3R,5R)-5-Ethyl-5-((2S,5S,6R)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-4-hydroxy-3,5-dimethyl-6-oxo-nonyl}-2-hydroxy-3-methyl-benzoic acid benzyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 97 percent / H₂ / W-2 Raney nickel catalyst / ethyl acetate / 12 h

2: 10percent aq. HCl / tetrahydrofuran / 12 h / 50 °C

3: 99 percent / oxalyl chloride, dimethyl sulfoxide, triethylamine / CH₂Cl₂ / 0.25 h / -60 °C

4: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, then room temp., 1 h, 2.) THF, -78 deg C, then room temp., 10 h

5: solid NaHCO₃, 80-90percent m-chloroperbenzoic acid / CH₂Cl₂ / 1.) 0 deg C, 2.) room temp., 3 h

6: 1.) cupric bromide-dimethyl sulfide complex / 1.) pentane, ether, 0 deg C, 30 min, 2.) pentane, 2 h

7: 97 percent / lithium wire, anhydrous ammonia / tetrahydrofuran / 1 h

8: oxalyl chloride, dimethyl sulfoxide, triethylamine / CH₂Cl₂ / 2 h / -60 °C

9: 87 percent / oxalyl chloride, dimethyl sulfoxide, triethylamine / CH₂Cl₂ / 2 h / -60 °C

With hydrogenchloride; n-butyllithium; oxalyl dichloride; copper bromide dimethyl sulfide complex; ammonia; hydrogen; lithium; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; W-2 Raney nickel catalyst; In tetrahydrofuran; dichloromethane; ethyl acetate;
DOI:10.1021/jo00174a008

Reference yield:

: 87678-29-3
benzyl 2(R)-<5(R)-carbomethoxy-3(R)-methyl-5-<5,6-dihydro-5(R)-(methoxymethoxy)-6(R)-methyl-2(S)-pyranyl>-2(R)-tetrahydrofuryl>butyl ether

: 87678-47-5
6-{(3S,4S,5S,7S)-7-[(2R,3R,5R)-5-Ethyl-5-((2S,5S,6R)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-4-hydroxy-3,5-dimethyl-6-oxo-nonyl}-2-hydroxy-3-methyl-benzoic acid benzyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 90 percent / H₂ / 5percent platinum on carbon / ethyl acetate / 12 h / 760 Torr

2: 89 percent / 1M diisobutylaluminum hydride / diethyl ether; methanol / 1 h / -78 °C

3: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, then room temp., 1 h, 2.) THF, -78 deg C, then room temp., 10 h

4: 97 percent / H₂ / W-2 Raney nickel catalyst / ethyl acetate / 12 h

5: 10percent aq. HCl / tetrahydrofuran / 12 h / 50 °C

6: 99 percent / oxalyl chloride, dimethyl sulfoxide, triethylamine / CH₂Cl₂ / 0.25 h / -60 °C

7: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, then room temp., 1 h, 2.) THF, -78 deg C, then room temp., 10 h

8: solid NaHCO₃, 80-90percent m-chloroperbenzoic acid / CH₂Cl₂ / 1.) 0 deg C, 2.) room temp., 3 h

9: 1.) cupric bromide-dimethyl sulfide complex / 1.) pentane, ether, 0 deg C, 30 min, 2.) pentane, 2 h

10: 97 percent / lithium wire, anhydrous ammonia / tetrahydrofuran / 1 h

11: oxalyl chloride, dimethyl sulfoxide, triethylamine / CH₂Cl₂ / 2 h / -60 °C

12: 87 percent / oxalyl chloride, dimethyl sulfoxide, triethylamine / CH₂Cl₂ / 2 h / -60 °C

With hydrogenchloride; n-butyllithium; oxalyl dichloride; copper bromide dimethyl sulfide complex; ammonia; hydrogen; lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; platinum on activated charcoal; W-2 Raney nickel catalyst; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate;
DOI:10.1021/jo00174a008