Toluene-4-sulfonic acid (E)-(2S,3R,7S,9S,10R,11S,13R)-3-allyl-13-[1,3]dithian-2-yl-2,10-dihydroxy-9,11-dimethoxy-5,7-dimethyl-tetradec-4-enyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (E)-(2S,3R,7S,9S,10R,11S,13R)-3-allyl-13-[1,3]dithian-2-yl-2,10-dihydroxy-9,11-dimethoxy-5,7-dimethyl-tetradec-4-enyl ester
• CAS No.: 158040-48-3
• Molecular Formula: C₃₂H₅₂O₇S₃
• Molecular Weight: 644.959

Synonyms:Toluene-4-sulfonic acid (E)-(2S,3R,7S,9S,10R,11S,13R)-3-allyl-13-[1,3]dithian-2-yl-2,10-dihydroxy-9,11-dimethoxy-5,7-dimethyl-tetradec-4-enyl ester

Chemical Property of Toluene-4-sulfonic acid (E)-(2S,3R,7S,9S,10R,11S,13R)-3-allyl-13-[1,3]dithian-2-yl-2,10-dihydroxy-9,11-dimethoxy-5,7-dimethyl-tetradec-4-enyl ester

Chemical Property:

Purity/Quality:

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Technology Process of Toluene-4-sulfonic acid (E)-(2S,3R,7S,9S,10R,11S,13R)-3-allyl-13-[1,3]dithian-2-yl-2,10-dihydroxy-9,11-dimethoxy-5,7-dimethyl-tetradec-4-enyl ester

There total 6 articles about Toluene-4-sulfonic acid (E)-(2S,3R,7S,9S,10R,11S,13R)-3-allyl-13-[1,3]dithian-2-yl-2,10-dihydroxy-9,11-dimethoxy-5,7-dimethyl-tetradec-4-enyl 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: 65.0%

p-toluenesulfonyl chloride (98-59-9) + (E)-(2S,3R,7S,9S,10R,11S,13R)-3-Allyl-13-[1,3]dithian-2-yl-9,11-dimethoxy-5,7-dimethyl-tetradec-4-ene-1,2,10-triol (158040-47-2) → Toluene-4-sulfonic acid (E)-(2S,3R,7S,9S,10R,11S,13R)-3-allyl-13-[1,3]dithian-2-yl-2,10-dihydroxy-9,11-dimethoxy-5,7-dimethyl-tetradec-4-enyl ester (158040-48-3)

Guidance literature:

With dmap; triethylamine; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4039(00)73331-4

Reference yield:

Toluene-4-sulfonic acid (E)-(2S,6S,8S)-2-((S)-2,2-diisopropyl-[1,3]dioxolan-4-yl)-8-((2R,3S,5R,6S)-3,6-dimethoxy-5-methyl-tetrahydro-pyran-2-yl)-8-methoxy-4,6-dimethyl-oct-3-enyl ester (158040-44-9) → Toluene-4-sulfonic acid (E)-(2S,3R,7S,9S,10R,11S,13R)-3-allyl-13-[1,3]dithian-2-yl-2,10-dihydroxy-9,11-dimethoxy-5,7-dimethyl-tetradec-4-enyl ester (158040-48-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 37 percent / CuCN / diethyl ether / 0 °C

2: 78 percent / BF₃*Et₂O / tetrahydrofuran / -78 deg C, 24 h, -50 deg C, 72 h

3: 65 percent / Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

With dmap; boron trifluoride diethyl etherate; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(00)73331-4

Reference yield:

(2S,3S)-3-[(E)-(4S,6S)-6-((2R,3S,5R,6S)-3,6-Dimethoxy-5-methyl-tetrahydro-pyran-2-yl)-6-methoxy-2,4-dimethyl-hex-1-enyl]-butane-1,2,4-triol (158040-42-7) → Toluene-4-sulfonic acid (E)-(2S,3R,7S,9S,10R,11S,13R)-3-allyl-13-[1,3]dithian-2-yl-2,10-dihydroxy-9,11-dimethoxy-5,7-dimethyl-tetradec-4-enyl ester (158040-48-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / TsOH / tetrahydrofuran / Ambient temperature

2: 95 percent / Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

3: 37 percent / CuCN / diethyl ether / 0 °C

4: 78 percent / BF₃*Et₂O / tetrahydrofuran / -78 deg C, 24 h, -50 deg C, 72 h

5: 65 percent / Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

With dmap; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(00)73331-4

upstream raw materials:

p-toluenesulfonyl chloride

(E)-(2S,3R,7S,9S,10R,11S,13R)-3-Allyl-13-[1,3]dithian-2-yl-9,11-dimethoxy-5,7-dimethyl-tetradec-4-ene-1,2,10-triol

(2S,3S)-3-[(E)-(4S,6S)-6-((2R,3S,5R,6S)-3,6-Dimethoxy-5-methyl-tetrahydro-pyran-2-yl)-6-methoxy-2,4-dimethyl-hex-1-enyl]-butane-1,2,4-triol

(E)-(2S,6S,8S)-2-((S)-2,2-Diisopropyl-[1,3]dioxolan-4-yl)-8-((2R,3S,5R,6S)-3,6-dimethoxy-5-methyl-tetrahydro-pyran-2-yl)-8-methoxy-4,6-dimethyl-oct-3-en-1-ol

Downstream raw materials:

C₆₈H₁₃₈O₁₀Si₄

Toluene-4-sulfonic acid (E)-(2S,3R,7S,9S,10R,11S,13R)-3-allyl-2,10-bis-(tert-butyl-dimethyl-silanyloxy)-13-[1,3]dithian-2-yl-9,11-dimethoxy-5,7-dimethyl-tetradec-4-enyl ester

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