Toluene-4-sulfonic acid (2S,4R)-2,4-dihydroxy-4-methyl-6-trimethylsilanyl-hex-5-ynyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (2S,4R)-2,4-dihydroxy-4-methyl-6-trimethylsilanyl-hex-5-ynyl ester
• CAS No.: 235100-41-1
• Molecular Formula: C₁₇H₂₆O₅SSi
• Molecular Weight: 370.542

Synonyms:Toluene-4-sulfonic acid (2S,4R)-2,4-dihydroxy-4-methyl-6-trimethylsilanyl-hex-5-ynyl ester

Chemical Property of Toluene-4-sulfonic acid (2S,4R)-2,4-dihydroxy-4-methyl-6-trimethylsilanyl-hex-5-ynyl ester

Chemical Property:

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Technology Process of Toluene-4-sulfonic acid (2S,4R)-2,4-dihydroxy-4-methyl-6-trimethylsilanyl-hex-5-ynyl ester

There total 2 articles about Toluene-4-sulfonic acid (2S,4R)-2,4-dihydroxy-4-methyl-6-trimethylsilanyl-hex-5-ynyl 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) + (2S,4R)-4-Methyl-6-trimethylsilanyl-hex-5-yne-1,2,4-triol (235100-40-0) → Toluene-4-sulfonic acid (2S,4R)-2,4-dihydroxy-4-methyl-6-trimethylsilanyl-hex-5-ynyl ester (235100-41-1)

Guidance literature:

With pyridine; at 0 ℃;

DOI:10.1055/s-1999-2697

Reference yield:

(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-propan-2-one (235100-38-6) → Toluene-4-sulfonic acid (2S,4R)-2,4-dihydroxy-4-methyl-6-trimethylsilanyl-hex-5-ynyl ester (235100-41-1)

Guidance literature:

Multi-step reaction with 3 steps

1: BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide

2: 98 percent / AcOH, H₂O

3: 90 percent / pyridine / 0 °C

With pyridine; n-butyllithium; water; acetic acid; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1055/s-1999-2697

Reference yield: 85.0%

2,2-dimethoxy-propane (77-76-9) + Toluene-4-sulfonic acid (2S,4R)-2,4-dihydroxy-4-methyl-6-trimethylsilanyl-hex-5-ynyl ester (235100-41-1) → Toluene-4-sulfonic acid (4S,6R)-2,2,6-trimethyl-6-trimethylsilanylethynyl-[1,3]dioxan-4-ylmethyl ester (235100-42-2)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane;

DOI:10.1055/s-1999-2697

upstream raw materials:

p-toluenesulfonyl chloride

(2S,4R)-4-Methyl-6-trimethylsilanyl-hex-5-yne-1,2,4-triol

(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-propan-2-one

Downstream raw materials:

Toluene-4-sulfonic acid (4S,6R)-2,2,6-trimethyl-6-trimethylsilanylethynyl-[1,3]dioxan-4-ylmethyl ester

(E)-(3R,5S,10R,12S)-12-(tert-Butyl-diphenyl-silanyloxy)-3,5-dihydroxy-3,10-dimethyl-tridec-8-en-1-yn-7-one

(2S,4R)-1-{2-[(E)-(3R,5S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-hex-1-enyl]-[1,3]dithian-2-yl}-4-methyl-hex-5-yne-2,4-diol

tert-Butyl-{(E)-(1S,3R)-5-[2-((4S,6R)-6-ethynyl-2,2,6-trimethyl-[1,3]dioxan-4-ylmethyl)-[1,3]dithian-2-yl]-1,3-dimethyl-pent-4-enyloxy}-diphenyl-silane

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