2,4,6-Triisopropyl-benzenesulfonic acid (3Z,5E)-(R)-2-hydroxy-7-trityloxy-hepta-3,5-dienyl ester

Base Information

Chemical Name:2,4,6-Triisopropyl-benzenesulfonic acid (3Z,5E)-(R)-2-hydroxy-7-trityloxy-hepta-3,5-dienyl ester
CAS No.:111670-25-8
Molecular Formula:C₄₁H₄₈O₅S
Molecular Weight:652.895
Hs Code.:

Synonyms:2,4,6-Triisopropyl-benzenesulfonic acid (3Z,5E)-(R)-2-hydroxy-7-trityloxy-hepta-3,5-dienyl ester

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Chemical Property of 2,4,6-Triisopropyl-benzenesulfonic acid (3Z,5E)-(R)-2-hydroxy-7-trityloxy-hepta-3,5-dienyl ester

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Technology Process of 2,4,6-Triisopropyl-benzenesulfonic acid (3Z,5E)-(R)-2-hydroxy-7-trityloxy-hepta-3,5-dienyl ester

There total 10 articles about 2,4,6-Triisopropyl-benzenesulfonic acid (3Z,5E)-(R)-2-hydroxy-7-trityloxy-hepta-3,5-dienyl 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: 63.0%

: 6553-96-4
2,4,6-triisopropylphenylsulfonyl chloride

: 111670-24-7
7-O-(triphenylmethyl)-3(Z),5(E)-heptadiene-1,2(S),7-triol

: 111670-25-8
2,4,6-Triisopropyl-benzenesulfonic acid (3Z,5E)-(R)-2-hydroxy-7-trityloxy-hepta-3,5-dienyl ester

Guidance literature:: With triethylamine; In dichloromethane; Ambient temperature;
DOI:10.1139/v87-244

Reference yield:

: 22900-10-3,35536-75-5,36792-85-5,113890-34-9,113890-37-2,133813-23-7
2-deoxy-D-ribose

: 111670-25-8
2,4,6-Triisopropyl-benzenesulfonic acid (3Z,5E)-(R)-2-hydroxy-7-trityloxy-hepta-3,5-dienyl ester

Guidance literature:: Multi-step reaction with 10 steps

2: (i-Pr)2NEt / DMAP / CH₂Cl₂

3: pyridine; CH₂Cl₂

4: DBU / pyridine

5: 92 percent / LDA / tetrahydrofuran / 0 °C

6: 89 percent / triphenylphosphine, DEAD / tetrahydrofuran / Ambient temperature

7: 79 percent / DIBAH / toluene / -10 deg C to room temp.

8: DMAP / pyridine / 50 °C

9: tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature

10: 63 percent / triethylamine / CH₂Cl₂ / Ambient temperature

With tetrabutyl ammonium fluoride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; dmap; In tetrahydrofuran; pyridine; dichloromethane; toluene;
DOI:10.1139/v87-244

Reference yield:

: 79308-52-4
ethyl 2-[(4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]acetate

: 111670-25-8
2,4,6-Triisopropyl-benzenesulfonic acid (3Z,5E)-(R)-2-hydroxy-7-trityloxy-hepta-3,5-dienyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: (i-Pr)2NEt / DMAP / CH₂Cl₂

2: pyridine; CH₂Cl₂

3: DBU / pyridine

4: 92 percent / LDA / tetrahydrofuran / 0 °C

5: 89 percent / triphenylphosphine, DEAD / tetrahydrofuran / Ambient temperature

6: 79 percent / DIBAH / toluene / -10 deg C to room temp.

7: DMAP / pyridine / 50 °C

8: tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature

9: 63 percent / triethylamine / CH₂Cl₂ / Ambient temperature

With tetrabutyl ammonium fluoride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; dmap; In tetrahydrofuran; pyridine; dichloromethane; toluene;
DOI:10.1139/v87-244