Oxiranemethanol, 3-(2-propenyl)-, 4-methylbenzenesulfonate, (2S,3S)-

Base Information

• Chemical Name: Oxiranemethanol, 3-(2-propenyl)-, 4-methylbenzenesulfonate, (2S,3S)-
• CAS No.: 393530-53-5
• Molecular Formula: C13H16O4S
• Molecular Weight: 268.334
• Mol file: 393530-53-5.mol

Synonyms:

Chemical Property of Oxiranemethanol, 3-(2-propenyl)-, 4-methylbenzenesulfonate, (2S,3S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Oxiranemethanol, 3-(2-propenyl)-, 4-methylbenzenesulfonate, (2S,3S)-

There total 1 articles about Oxiranemethanol, 3-(2-propenyl)-, 4-methylbenzenesulfonate, (2S,3S)- 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: 85.0%

p-toluenesulfonyl chloride (98-59-9) + ((2S,3S)-3-allyloxiran-2-yl)methanol (353490-93-4) → (2S,3S)-1-p-toluenesulfonyloxy-2,3-epoxy-5-hexene (393530-53-5)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 16h;

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

Reference yield:

(2S,3S)-1-p-toluenesulfonyloxy-2,3-epoxy-5-hexene (393530-53-5) → (+)-ambruticin S (58857-02-6)

Guidance literature:

Multi-step reaction with 11 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

9.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

9.2: 31 mg / tetrahydrofuran; hexane / 2 h / -78 °C

10.1: Na₂HPO₄; sodium amalgam / methanol / 3 h / -30 °C

10.2: 9 mg / HF*pyridine / tetrahydrofuran / 16 h / 20 °C

11.1: 95 percent / aq. LiOH / tetrahydrofuran / 3.5 h / 20 °C

With lithium hydroxide; disodium hydrogenphosphate; sodium amalgam; lithium aluminium tetrahydride; n-butyllithium; 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; methanol; diethyl ether; ethanol; hexane; dichloromethane; benzene; 9.2: Julia coupling;

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

Reference yield:

(2S,3S)-1-p-toluenesulfonyloxy-2,3-epoxy-5-hexene (393530-53-5) → [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 (1054631-66-1)

Guidance literature:

Multi-step reaction with 9 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

9.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

9.2: 31 mg / tetrahydrofuran; hexane / 2 h / -78 °C

With lithium aluminium tetrahydride; n-butyllithium; 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; hexane; dichloromethane; benzene; 9.2: Julia coupling;

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

upstream raw materials:

p-toluenesulfonyl chloride

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

Downstream raw materials:

Toluene-4-sulfonic acid (2S,3R)-3-((R)-1-ethyl-2-methyl-allyloxy)-2-hydroxy-hex-5-enyl ester

(+)-ambruticin S

1-[(2R,6R)-6-ethyl-5-methyl-3,6-dihydro-2H-2-pyranyl]-1-ethanone

[2R,6R,2(2'R)]-2-[2'-hydroxy-3'-penten-2'(Z)-yl]-5-methyl-6-ethyl-3,6-dihydropyran