3-(benzyloxymethyl)-1-[(1'S,2'S,4'S,5'R)-4'-hydroxy-5'-(hydroxymethyl)bicyclo[3.1.0]hexan-2'-yl]-5-methylpyrimidine-2,4(1H,3H)-dione

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Chemical Name:3-(benzyloxymethyl)-1-[(1'S,2'S,4'S,5'R)-4'-hydroxy-5'-(hydroxymethyl)bicyclo[3.1.0]hexan-2'-yl]-5-methylpyrimidine-2,4(1H,3H)-dione
CAS No.:1004771-19-0
Molecular Formula:C₂₀H₂₄N₂O₅
Molecular Weight:372.421
Hs Code.:

Synonyms:3-(benzyloxymethyl)-1-[(1'S,2'S,4'S,5'R)-4'-hydroxy-5'-(hydroxymethyl)bicyclo[3.1.0]hexan-2'-yl]-5-methylpyrimidine-2,4(1H,3H)-dione

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Chemical Property of 3-(benzyloxymethyl)-1-[(1'S,2'S,4'S,5'R)-4'-hydroxy-5'-(hydroxymethyl)bicyclo[3.1.0]hexan-2'-yl]-5-methylpyrimidine-2,4(1H,3H)-dione

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Technology Process of 3-(benzyloxymethyl)-1-[(1'S,2'S,4'S,5'R)-4'-hydroxy-5'-(hydroxymethyl)bicyclo[3.1.0]hexan-2'-yl]-5-methylpyrimidine-2,4(1H,3H)-dione

There total 14 articles about 3-(benzyloxymethyl)-1-[(1'S,2'S,4'S,5'R)-4'-hydroxy-5'-(hydroxymethyl)bicyclo[3.1.0]hexan-2'-yl]-5-methylpyrimidine-2,4(1H,3H)-dione 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: 99.0%

: 3-Benzyloxymethyl-5-methyl-1-((1R,8S,10S,11S)-4,4,6,6-tetraisopropyl-3,5,7-trioxa-4,6-disila-tricyclo[6.4.0.0^1,11]dodec-10-yl)-1H-pyrimidine-2,4-dione

: 1004771-19-0
3-(benzyloxymethyl)-1-[(1'S,2'S,4'S,5'R)-4'-hydroxy-5'-(hydroxymethyl)bicyclo[3.1.0]hexan-2'-yl]-5-methylpyrimidine-2,4(1H,3H)-dione

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 4h; Ambient temperature;
DOI:10.1016/0040-4039(94)85212-X

Reference yield: 65.0%

: 119451-90-0
3-((benzyloxy)methyl)-5-methylpyrimidine-2,4(1H,3H)-dione

: 452335-24-9
(1R,2S,4R,5S)-(2-acetoxy-4-hydroxybicyclo[3.1.0]hex-1-yl)methyl acetate

: 1004771-20-3
3-(benzyloxymethyl)-2-[(1'S,2'S,4'S,5'R)-4'-hydroxy-5'-(hydroxymethyl)bicyclo[3.1.0]hexan-2'-yloxy]-5-methylpyrimidin-4(3H)-one

: 1004771-19-0
3-(benzyloxymethyl)-1-[(1'S,2'S,4'S,5'R)-4'-hydroxy-5'-(hydroxymethyl)bicyclo[3.1.0]hexan-2'-yl]-5-methylpyrimidine-2,4(1H,3H)-dione

Guidance literature:: 3-((benzyloxy)methyl)-5-methylpyrimidine-2,4(1H,3H)-dione; (1R,2S,4R,5S)-(2-acetoxy-4-hydroxybicyclo[3.1.0]hex-1-yl)methyl acetate; With di-isopropyl azodicarboxylate; triphenylphosphine; In acetonitrile; at -40 - 20 ℃; for 15h;

In methanol; at 20 ℃; for 5h; Further stages.;
DOI:10.1055/s-2007-990847

Reference yield:

: 89291-76-9
(1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol

: 1004771-19-0
3-(benzyloxymethyl)-1-[(1'S,2'S,4'S,5'R)-4'-hydroxy-5'-(hydroxymethyl)bicyclo[3.1.0]hexan-2'-yl]-5-methylpyrimidine-2,4(1H,3H)-dione

Guidance literature:: Multi-step reaction with 12 steps

1: 73 percent / Zn/Cu / diethyl ether / 18 h / Heating

2: 77 percent / Et₃N, DMAP / CH₂Cl₂ / 48 h / Ambient temperature

3: 88 percent / NaN₃ / dimethylformamide / 18 h / 70 °C

4: H₂ / Lindlar's catalyst / 4 h

5: 95 percent / CH₂Cl₂ / 0.5 h / -78 - 25 °C

6: 80 percent / 0.2 N aq. HCl / ethanol / 20 h / Heating

7: H₂ / 10 percent Pd-C / methanol; ethyl acetate

8: imidazole / dimethylformamide

9: 85 percent / DBU / acetonitrile / 1 h / Ambient temperature

10: 90 percent / DMAP, Et₃N / CH₂Cl₂ / RT, 3 h, 40 deg C, 18 h

11: 65 percent / Bu₃SnH, AIBN / 1,2-dimethoxy-ethane / 3 h / 80 °C

12: 99 percent / TBAF / tetrahydrofuran / 4 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; dmap; sodium azide; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; copper; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; zinc; palladium on activated charcoal; Lindlar's catalyst; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/0040-4039(94)85212-X