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

Base Information

Chemical Name:(1R,2S,3S,4R)-1-Benzyloxy-2-((E)-1,5-dimethyl-hex-1-enyl)-3,4-dihydroxy-cyclopentanecarboxylic acid methyl ester
CAS No.:863453-42-3
Molecular Formula:C₂₂H₃₂O₅
Molecular Weight:376.493
Hs Code.:

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

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Chemical Property of (1R,2S,3S,4R)-1-Benzyloxy-2-((E)-1,5-dimethyl-hex-1-enyl)-3,4-dihydroxy-cyclopentanecarboxylic acid methyl ester

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Technology Process of (1R,2S,3S,4R)-1-Benzyloxy-2-((E)-1,5-dimethyl-hex-1-enyl)-3,4-dihydroxy-cyclopentanecarboxylic acid methyl ester

There total 1 articles about (1R,2S,3S,4R)-1-Benzyloxy-2-((E)-1,5-dimethyl-hex-1-enyl)-3,4-dihydroxy-cyclopentanecarboxylic acid methyl 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: 98.0%

: (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

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

Guidance literature:: With pyridinium p-toluenesulfonate; In methanol; for 20h; Heating;
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

: 863453-44-5
(1R,4R,5S,6S)-4-Benzyloxy-5-((E)-1,5-dimethyl-hex-1-enyl)-6-methoxy-2-oxa-bicyclo[2.2.1]heptan-3-one

Guidance literature:: Multi-step reaction with 3 steps

1: DBU / acetonitrile / 6 h / Heating

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

3: 80 percent / Ag₂O / 4 h / Heating

With sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; silver(l) oxide; In methanol; 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