N-((S)-1-{(2S,5S)-5-[(E)-(S)-1-Hydroxy-7-((4S,5R)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hept-4-enyl]-tetrahydro-furan-2-yl}-ethyl)-4-methyl-benzenesulfonamide

Base Information

Chemical Name:N-((S)-1-{(2S,5S)-5-[(E)-(S)-1-Hydroxy-7-((4S,5R)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hept-4-enyl]-tetrahydro-furan-2-yl}-ethyl)-4-methyl-benzenesulfonamide
CAS No.:186642-43-3
Molecular Formula:C₂₇H₄₃NO₆S
Molecular Weight:509.708
Hs Code.:

Synonyms:N-((S)-1-{(2S,5S)-5-[(E)-(S)-1-Hydroxy-7-((4S,5R)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hept-4-enyl]-tetrahydro-furan-2-yl}-ethyl)-4-methyl-benzenesulfonamide

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Chemical Property of N-((S)-1-{(2S,5S)-5-[(E)-(S)-1-Hydroxy-7-((4S,5R)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hept-4-enyl]-tetrahydro-furan-2-yl}-ethyl)-4-methyl-benzenesulfonamide

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Technology Process of N-((S)-1-{(2S,5S)-5-[(E)-(S)-1-Hydroxy-7-((4S,5R)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hept-4-enyl]-tetrahydro-furan-2-yl}-ethyl)-4-methyl-benzenesulfonamide

There total 21 articles about N-((S)-1-{(2S,5S)-5-[(E)-(S)-1-Hydroxy-7-((4S,5R)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hept-4-enyl]-tetrahydro-furan-2-yl}-ethyl)-4-methyl-benzenesulfonamide 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:

: 186040-07-3
4-Methyl-N-((S)-1-{(2S,5S)-5-[(E)-7-((4S,5R)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hept-4-enoyl]-tetrahydro-furan-2-yl}-ethyl)-benzenesulfonamide

: 186642-43-3
N-((S)-1-{(2S,5S)-5-[(E)-(S)-1-Hydroxy-7-((4S,5R)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hept-4-enyl]-tetrahydro-furan-2-yl}-ethyl)-4-methyl-benzenesulfonamide

Guidance literature:: With L-Selectride; at -95 - -60 ℃; for 3h; Yield given;

Reference yield:

: 4816-81-3,21957-58-4,85471-45-0
p-tosyl-L-alanine

: 186642-43-3
N-((S)-1-{(2S,5S)-5-[(E)-(S)-1-Hydroxy-7-((4S,5R)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hept-4-enyl]-tetrahydro-furan-2-yl}-ethyl)-4-methyl-benzenesulfonamide

Guidance literature:: Multi-step reaction with 9 steps

1: 50 percent / n-BuLi / 1.) Et₂O, -78 to -50 deg C, 1 h, 2.) 0 deg C, 15 h

2: 80 percent / L-Selectride / tetrahydrofuran / 1 h / -95 °C

3: mCPBA / CH₂Cl₂ / 6 h / Ambient temperature

4: p-TsOH / CH₂Cl₂ / 2 h / Ambient temperature

5: 85 percent / DMSO, (COCl)2, Et₃N / CH₂Cl₂

6: 78 percent / n-BuLi / tetrahydrofuran / 1.) -50 deg C, 1 h, 2.) -78 to -30 deg C, 4 h

7: 96 percent / periodinane, pyridine / CH₂Cl₂ / 4 h / Ambient temperature

8: 80 percent / Al/Hg / tetrahydrofuran; propan-1-ol; H₂O / 3 h / 40 °C

9: L-Selectride / 3 h / -95 - -60 °C

With pyridine; aluminum amalgam; n-butyllithium; oxalyl dichloride; L-Selectride; Dess-Martin periodane; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; propan-1-ol; dichloromethane; water;

Reference yield:

: 94233-74-6
(2R,3S)-1-(benzyloxy)-2-methylhex-5-en-3-ol

: 186642-43-3
N-((S)-1-{(2S,5S)-5-[(E)-(S)-1-Hydroxy-7-((4S,5R)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hept-4-enyl]-tetrahydro-furan-2-yl}-ethyl)-4-methyl-benzenesulfonamide

Guidance literature:: Multi-step reaction with 15 steps

1: 98 percent / Na, NH₃ / tetrahydrofuran / 1 h / -40 °C

2: 95 percent / p-TsOH / CH₂Cl₂; acetone / 4 h / Ambient temperature

3: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2) -78 deg C to r.t.

4: NaBH₄ / methanol / 12 h

5: pyridine

6: LiBr / tetrahydrofuran / 4 h / 50 °C

7: 82 percent / LiNH₂, NH₃ / dimethylsulfoxide / 7 h / -40 - 0 °C

8: 89 percent / Na, NH₃ / tetrahydrofuran / 4 h / -35 °C

9: pyridine

10: LiBr / tetrahydrofuran / 2.5 h / 50 °C

11: 90 percent / H₂O; various solvent(s) / 3 h / 130 °C

12: 78 percent / n-BuLi / tetrahydrofuran / 1.) -50 deg C, 1 h, 2.) -78 to -30 deg C, 4 h

13: 96 percent / periodinane, pyridine / CH₂Cl₂ / 4 h / Ambient temperature

14: 80 percent / Al/Hg / tetrahydrofuran; propan-1-ol; H₂O / 3 h / 40 °C

15: L-Selectride / 3 h / -95 - -60 °C

With pyridine; sodium tetrahydroborate; aluminum amalgam; n-butyllithium; lithium amide; ammonia; sodium; L-Selectride; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; triphenylphosphine; lithium bromide; In tetrahydrofuran; methanol; propan-1-ol; dichloromethane; water; dimethyl sulfoxide; acetone;