Toluene-4-sulfonic acid 2-((2R,3S)-3-but-3-enyloxy-tetrahydro-pyran-2-yl)-ethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid 2-((2R,3S)-3-but-3-enyloxy-tetrahydro-pyran-2-yl)-ethyl ester
• CAS No.: 176738-55-9
• Molecular Formula: C₁₈H₂₆O₅S
• Molecular Weight: 354.467
• Mol file: 176738-55-9.mol

Synonyms:Toluene-4-sulfonic acid 2-((2R,3S)-3-but-3-enyloxy-tetrahydro-pyran-2-yl)-ethyl ester

Chemical Property of Toluene-4-sulfonic acid 2-((2R,3S)-3-but-3-enyloxy-tetrahydro-pyran-2-yl)-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid 2-((2R,3S)-3-but-3-enyloxy-tetrahydro-pyran-2-yl)-ethyl ester

There total 11 articles about Toluene-4-sulfonic acid 2-((2R,3S)-3-but-3-enyloxy-tetrahydro-pyran-2-yl)-ethyl 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: 90.0%

p-toluenesulfonyl chloride (98-59-9) + 2-((2R,3S)-3-But-3-enyloxy-tetrahydro-pyran-2-yl)-ethanol (176738-54-8) → Toluene-4-sulfonic acid 2-((2R,3S)-3-but-3-enyloxy-tetrahydro-pyran-2-yl)-ethyl ester (176738-55-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 8h;

DOI:10.1016/0040-4039(96)00408-X

Reference yield:

(2R,3S)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol (125901-90-8) → Toluene-4-sulfonic acid 2-((2R,3S)-3-but-3-enyloxy-tetrahydro-pyran-2-yl)-ethyl ester (176738-55-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 99 percent / hydrogen / 10percent Pd/C / methanol / 8 h

2: 77 percent / Et₃N, DMAP / CH₂Cl₂ / 8 h / 0 °C

3: 80 percent / Ac₂O / acetic acid / 48 h / 25 °C

4: 100 percent / NaIO₄, RuCl₃ / acetonitrile; CCl₄; H₂O / 0.25 h / 25 °C

5: 80 percent / AlCl₃ / CH₂Cl₂ / 6 h / -78 - 20 °C

6: 95 percent / dimethylsulfoxide / 8 h / 50 °C

7: 1) DIBAL, 2) 0.1N HCl / 1) Et₂O, 0 deg C, 6 h

8: NaBH₄ / methanol / 0.5 h / 0 °C

9: 90 percent / Et₃N, DMAP / CH₂Cl₂ / 8 h

With hydrogenchloride; dmap; ruthenium trichloride; sodium tetrahydroborate; sodium periodate; aluminium trichloride; hydrogen; acetic anhydride; diisobutylaluminium hydride; triethylamine; palladium on activated charcoal; In methanol; tetrachloromethane; dichloromethane; water; acetic acid; dimethyl sulfoxide; acetonitrile;

DOI:10.1016/0040-4039(96)00408-X

Reference yield:

((2R,3S)-3-acetoxy-3,6-dihydro-2H-pyran-2-yl)methyl acetate (149342-25-6,92131-91-4) → Toluene-4-sulfonic acid 2-((2R,3S)-3-but-3-enyloxy-tetrahydro-pyran-2-yl)-ethyl ester (176738-55-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 100 percent / NaOMe / methanol / 0.5 h

2: 99 percent / hydrogen / 10percent Pd/C / methanol / 8 h

3: 77 percent / Et₃N, DMAP / CH₂Cl₂ / 8 h / 0 °C

4: 80 percent / Ac₂O / acetic acid / 48 h / 25 °C

5: 100 percent / NaIO₄, RuCl₃ / acetonitrile; CCl₄; H₂O / 0.25 h / 25 °C

6: 80 percent / AlCl₃ / CH₂Cl₂ / 6 h / -78 - 20 °C

7: 95 percent / dimethylsulfoxide / 8 h / 50 °C

8: 1) DIBAL, 2) 0.1N HCl / 1) Et₂O, 0 deg C, 6 h

9: NaBH₄ / methanol / 0.5 h / 0 °C

10: 90 percent / Et₃N, DMAP / CH₂Cl₂ / 8 h

With hydrogenchloride; dmap; ruthenium trichloride; sodium tetrahydroborate; sodium periodate; aluminium trichloride; hydrogen; sodium methylate; acetic anhydride; diisobutylaluminium hydride; triethylamine; palladium on activated charcoal; In methanol; tetrachloromethane; dichloromethane; water; acetic acid; dimethyl sulfoxide; acetonitrile;

DOI:10.1016/0040-4039(96)00408-X

upstream raw materials:

p-toluenesulfonyl chloride

2-((2R,3S)-3-But-3-enyloxy-tetrahydro-pyran-2-yl)-ethanol

(2R,3S)-2-hydroxymethyltetrahydropyran-3-ol

(2R,3S)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol