Phenyl-carbamic acid (2R,3aR,4S,7aS)-4-hydroxy-1-[5-methoxymethoxy-5-methyl-hex-(Z)-ylidene]-7a-methyl-octahydro-inden-2-yl ester

Base Information

Chemical Name:Phenyl-carbamic acid (2R,3aR,4S,7aS)-4-hydroxy-1-[5-methoxymethoxy-5-methyl-hex-(Z)-ylidene]-7a-methyl-octahydro-inden-2-yl ester
CAS No.:228420-93-7
Molecular Formula:C₂₆H₃₉NO₅
Molecular Weight:445.599
Hs Code.:

Synonyms:Phenyl-carbamic acid (2R,3aR,4S,7aS)-4-hydroxy-1-[5-methoxymethoxy-5-methyl-hex-(Z)-ylidene]-7a-methyl-octahydro-inden-2-yl ester

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Chemical Property of Phenyl-carbamic acid (2R,3aR,4S,7aS)-4-hydroxy-1-[5-methoxymethoxy-5-methyl-hex-(Z)-ylidene]-7a-methyl-octahydro-inden-2-yl ester

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Technology Process of Phenyl-carbamic acid (2R,3aR,4S,7aS)-4-hydroxy-1-[5-methoxymethoxy-5-methyl-hex-(Z)-ylidene]-7a-methyl-octahydro-inden-2-yl ester

There total 9 articles about Phenyl-carbamic acid (2R,3aR,4S,7aS)-4-hydroxy-1-[5-methoxymethoxy-5-methyl-hex-(Z)-ylidene]-7a-methyl-octahydro-inden-2-yl 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: 85.0%

: 103-71-9
phenyl isocyanate

: 228420-80-2
(2R,3aR,4S,7aS)-1-[5-Methoxymethoxy-5-methyl-hex-(Z)-ylidene]-7a-methyl-octahydro-indene-2,4-diol

: 228420-93-7
Phenyl-carbamic acid (2R,3aR,4S,7aS)-4-hydroxy-1-[5-methoxymethoxy-5-methyl-hex-(Z)-ylidene]-7a-methyl-octahydro-inden-2-yl ester

Guidance literature:: With dmap; In pyridine; at -25 ℃; for 20h;
DOI:10.1021/jo982393e

Reference yield:

: 2067-33-6
5-bromopentanoic acid

: 228420-93-7
Phenyl-carbamic acid (2R,3aR,4S,7aS)-4-hydroxy-1-[5-methoxymethoxy-5-methyl-hex-(Z)-ylidene]-7a-methyl-octahydro-inden-2-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 96 percent / acetonitrile / 24 h / 80 °C

2: 1.) t-BuOK / 1.) C₆H₆, reflux, 2 h, 2.) C₆H₆, 80 deg C, 36 h

3: 1.) THF, Et₂O, room temperature, 12 h, 2) THF, Et₂O, -78 deg C, 3 h; -78 deg C to room temperature, 3 h

4: 92 percent / DMAP, i-Pr₂NEt / CH₂Cl₂ / 24 h / 0 °C

5: 90 percent / t-BuOOH, SeO₂ / CH₂Cl₂ / 6 h / Ambient temperature

6: 86 percent / m-CPBA, NaHCO₃ / CH₂Cl₂; H₂O / 5 h / Ambient temperature

7: 1.) n-BuLi, HPPh₂, 2.) MeI / 1.) THF, hexane, 48 h, 2.) 0 deg C, 4 h

8: 99 percent / TBAF / tetrahydrofuran / 24 h / Heating

9: 85 percent / DMAP / pyridine / 20 h / -25 °C

With tert.-butylhydroperoxide; dmap; n-butyllithium; selenium(IV) oxide; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; diphenylphosphane; methyl iodide; In tetrahydrofuran; pyridine; dichloromethane; water; acetonitrile;
DOI:10.1021/jo982393e

Reference yield:

: 17814-85-6
(4-carboxybutyl)triphenylphosphonium bromide

: 228420-93-7
Phenyl-carbamic acid (2R,3aR,4S,7aS)-4-hydroxy-1-[5-methoxymethoxy-5-methyl-hex-(Z)-ylidene]-7a-methyl-octahydro-inden-2-yl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) t-BuOK / 1.) C₆H₆, reflux, 2 h, 2.) C₆H₆, 80 deg C, 36 h

2: 1.) THF, Et₂O, room temperature, 12 h, 2) THF, Et₂O, -78 deg C, 3 h; -78 deg C to room temperature, 3 h

3: 92 percent / DMAP, i-Pr₂NEt / CH₂Cl₂ / 24 h / 0 °C

4: 90 percent / t-BuOOH, SeO₂ / CH₂Cl₂ / 6 h / Ambient temperature

5: 86 percent / m-CPBA, NaHCO₃ / CH₂Cl₂; H₂O / 5 h / Ambient temperature

6: 1.) n-BuLi, HPPh₂, 2.) MeI / 1.) THF, hexane, 48 h, 2.) 0 deg C, 4 h

7: 99 percent / TBAF / tetrahydrofuran / 24 h / Heating

8: 85 percent / DMAP / pyridine / 20 h / -25 °C

With tert.-butylhydroperoxide; dmap; n-butyllithium; selenium(IV) oxide; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; diphenylphosphane; methyl iodide; In tetrahydrofuran; pyridine; dichloromethane; water;
DOI:10.1021/jo982393e