Toluene-4-sulfonic acid (1R,2S,3S,4R)-2-((E)-1,5-dimethyl-hex-1-enyl)-1,4-dihydroxy-3-methoxy-cyclopentylmethyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (1R,2S,3S,4R)-2-((E)-1,5-dimethyl-hex-1-enyl)-1,4-dihydroxy-3-methoxy-cyclopentylmethyl ester
CAS No.:863453-55-8
Molecular Formula:C₂₂H₃₄O₆S
Molecular Weight:426.574
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (1R,2S,3S,4R)-2-((E)-1,5-dimethyl-hex-1-enyl)-1,4-dihydroxy-3-methoxy-cyclopentylmethyl ester

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Chemical Property of Toluene-4-sulfonic acid (1R,2S,3S,4R)-2-((E)-1,5-dimethyl-hex-1-enyl)-1,4-dihydroxy-3-methoxy-cyclopentylmethyl ester

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Technology Process of Toluene-4-sulfonic acid (1R,2S,3S,4R)-2-((E)-1,5-dimethyl-hex-1-enyl)-1,4-dihydroxy-3-methoxy-cyclopentylmethyl ester

There total 6 articles about Toluene-4-sulfonic acid (1R,2S,3S,4R)-2-((E)-1,5-dimethyl-hex-1-enyl)-1,4-dihydroxy-3-methoxy-cyclopentylmethyl 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: 80.0%

: 863453-45-6
(1R,3R,4S,5S)-5-((E)-1,5-Dimethyl-hex-1-enyl)-1-hydroxymethyl-4-methoxy-cyclopentane-1,3-diol

: 98-59-9
p-toluenesulfonyl chloride

: 863453-55-8
Toluene-4-sulfonic acid (1R,2S,3S,4R)-2-((E)-1,5-dimethyl-hex-1-enyl)-1,4-dihydroxy-3-methoxy-cyclopentylmethyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 18h;
DOI:10.1016/j.bmcl.2005.05.065

Reference yield:

: (3aS,4S,6aR)-5-Benzyloxy-4-((E)-1,5-dimethyl-hex-1-enyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole-5-carboxylic acid methyl ester

: 863453-55-8
Toluene-4-sulfonic acid (1R,2S,3S,4R)-2-((E)-1,5-dimethyl-hex-1-enyl)-1,4-dihydroxy-3-methoxy-cyclopentylmethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 98 percent / PPTS / methanol / 20 h / Heating

2: DBU / acetonitrile / 6 h / Heating

3: 95 percent / NaOMe / methanol / 6 h / 20 °C

4: 80 percent / Ag₂O / 4 h / Heating

5: 62 percent / Li; liq. NH₃ / 3 h / -78 °C

6: 80 percent / Et₃N; DMAP / CH₂Cl₂ / 18 h / 20 °C

With dmap; ammonia; sodium methylate; pyridinium p-toluenesulfonate; lithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; silver(l) oxide; In methanol; dichloromethane; acetonitrile;
DOI:10.1016/j.bmcl.2005.05.065

Reference yield:

: 863453-42-3
(1R,2S,3S,4R)-1-Benzyloxy-2-((E)-1,5-dimethyl-hex-1-enyl)-3,4-dihydroxy-cyclopentanecarboxylic acid methyl ester

: 863453-55-8
Toluene-4-sulfonic acid (1R,2S,3S,4R)-2-((E)-1,5-dimethyl-hex-1-enyl)-1,4-dihydroxy-3-methoxy-cyclopentylmethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: DBU / acetonitrile / 6 h / Heating

2: 95 percent / NaOMe / methanol / 6 h / 20 °C

3: 80 percent / Ag₂O / 4 h / Heating

4: 62 percent / Li; liq. NH₃ / 3 h / -78 °C

5: 80 percent / Et₃N; DMAP / CH₂Cl₂ / 18 h / 20 °C

With dmap; ammonia; sodium methylate; lithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; silver(l) oxide; In methanol; dichloromethane; acetonitrile;
DOI:10.1016/j.bmcl.2005.05.065