2H-Pyran, 6-[(1E,3S)-1,3-dimethyl-4-(phenylsulfonyl)-1-butenyl]-2-ethyl-5,6-dihydro -3-methyl-, (2R,6R)-

Base Information

• Chemical Name: 2H-Pyran, 6-[(1E,3S)-1,3-dimethyl-4-(phenylsulfonyl)-1-butenyl]-2-ethyl-5,6-dihydro -3-methyl-, (2R,6R)-
• CAS No.: 393530-21-7
• Molecular Formula: C20H28O3S
• Molecular Weight: 348.507
• Mol file: 393530-21-7.mol

Synonyms:

Chemical Property of 2H-Pyran, 6-[(1E,3S)-1,3-dimethyl-4-(phenylsulfonyl)-1-butenyl]-2-ethyl-5,6-dihydro -3-methyl-, (2R,6R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2H-Pyran, 6-[(1E,3S)-1,3-dimethyl-4-(phenylsulfonyl)-1-butenyl]-2-ethyl-5,6-dihydro -3-methyl-, (2R,6R)-

There total 13 articles about 2H-Pyran, 6-[(1E,3S)-1,3-dimethyl-4-(phenylsulfonyl)-1-butenyl]-2-ethyl-5,6-dihydro -3-methyl-, (2R,6R)- 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: 98.0%

[2R,6R,2(2'S,3'E)]-2-(1-phenylthio-2-methyl-3-penten-4-yl)-5-methyl-6-ethyl-3,6-dihydropyran (616895-73-9) → [2R,6R,2(2'S,3'E)]-2-(1-phenylsulfonyl-2-methyl-3-penten-4-yl)-5-methyl-6-ethyl-3,6-dihydropyran (393530-21-7)

Guidance literature:

With ammonium molybdate(VI) tetrahydrate; dihydrogen peroxide; In ethanol; at -10 ℃; for 0.5h;

DOI:10.1016/S0040-4020(03)00370-3

Reference yield:

N-(phenylthio)succinimide (14204-24-1) → [2R,6R,2(2'S,3'E)]-2-(1-phenylsulfonyl-2-methyl-3-penten-4-yl)-5-methyl-6-ethyl-3,6-dihydropyran (393530-21-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / PBu₃ / benzene / 1 h

2: 98 percent / ammonium molybdate tetrahydrate; aq. H₂O₂ / ethanol / 0.5 h / -10 °C

With ammonium molybdate(VI) tetrahydrate; tributylphosphine; dihydrogen peroxide; In ethanol; benzene;

DOI:10.1016/S0040-4020(03)00370-3

Reference yield:

(R)-3-hydroxy-2-methylpent-1-ene (125637-07-2,2088-07-5) → [2R,6R,2(2'S,3'E)]-2-(1-phenylsulfonyl-2-methyl-3-penten-4-yl)-5-methyl-6-ethyl-3,6-dihydropyran (393530-21-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: BF₃*OEt₃ / CH₂Cl₂ / 16 h / 20 °C

2.1: 4.0 g / LiAlH₄ / diethyl ether / 3 h / 0 °C

3.1: Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / 16 h / Heating

4.1: 60 percent / 4 Angstroem molecular sieves; NMO; TPAP / CH₂Cl₂ / 2 h / 20 °C

5.1: 75 percent / tetrahydrofuran / 1 h / -78 °C

6.1: 18-crown-6; KH / tetrahydrofuran / 3 h / 20 °C

6.2: 70 percent / n-BuLi / tetrahydrofuran; hexane / 3 h / -78 °C

7.1: 91 percent / PBu₃ / benzene / 1 h

8.1: 98 percent / ammonium molybdate tetrahydrate; aq. H₂O₂ / ethanol / 0.5 h / -10 °C

With lithium aluminium tetrahydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; ammonium molybdate(VI) tetrahydrate; 18-crown-6 ether; tributylphosphine; 4 A molecular sieve; boron trifluoride diethyl etherate; dihydrogen peroxide; potassium hydride; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; benzene;

DOI:10.1016/S0040-4020(03)00370-3

upstream raw materials:

[2R,6R,2(2'S,3'E)]-2-(1-phenylthio-2-methyl-3-penten-4-yl)-5-methyl-6-ethyl-3,6-dihydropyran

N-(phenylthio)succinimide

(R)-3-hydroxy-2-methylpent-1-ene

((2S,3S)-3-allyloxiran-2-yl)methanol

Downstream raw materials:

[6-(2-{2-[2-benzenesulfonyl-5-(6-ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)-1-hydroxy-3-methyl-hex-4-enyl]-3-methyl-cyclopropyl}-vinyl)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-acetic acid methyl ester

(+)-ambruticin S