<4R-<4α(2E,4E),4aβ,7α(2S*,3E),8β,8aβ>>-1H-imidazole-1-carboxylic acid 5--3-butenyl>-4a,8-dimethyl-2,5-dioxo-2H,5H-pyrano<3,4-e>-1,3-oxazin-4-yl>-4-methyl-2,4-pentadienyl ester

Base Information

Chemical Name:<4R-<4α(2E,4E),4aβ,7α(2S*,3E),8β,8aβ>>-1H-imidazole-1-carboxylic acid 5--3-butenyl>-4a,8-dimethyl-2,5-dioxo-2H,5H-pyrano<3,4-e>-1,3-oxazin-4-yl>-4-methyl-2,4-pentadienyl ester
CAS No.:152453-83-3
Molecular Formula:C₃₁H₃₆IN₃O₈
Molecular Weight:705.547
Hs Code.:

<4R-<4α(2E,4E),4aβ,7α(2S*,3E),8β,8aβ>>-1H-imidazole-1-carboxylic acid 5-<hexahydro-7-<4-iodo-2-<(4-methoxyphenyl)methoxy>-3-butenyl>-4a,8-dimethyl-2,5-dioxo-2H,5H-pyrano<3,4-e>-1,3-oxazin-4-yl>-4-methyl-2,4-pentadienyl ester

Synonyms:<4R-<4α(2E,4E),4aβ,7α(2S*,3E),8β,8aβ>>-1H-imidazole-1-carboxylic acid 5--3-butenyl>-4a,8-dimethyl-2,5-dioxo-2H,5H-pyrano<3,4-e>-1,3-oxazin-4-yl>-4-methyl-2,4-pentadienyl ester

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Chemical Property of <4R-<4α(2E,4E),4aβ,7α(2S*,3E),8β,8aβ>>-1H-imidazole-1-carboxylic acid 5--3-butenyl>-4a,8-dimethyl-2,5-dioxo-2H,5H-pyrano<3,4-e>-1,3-oxazin-4-yl>-4-methyl-2,4-pentadienyl ester

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Technology Process of <4R-<4α(2E,4E),4aβ,7α(2S*,3E),8β,8aβ>>-1H-imidazole-1-carboxylic acid 5--3-butenyl>-4a,8-dimethyl-2,5-dioxo-2H,5H-pyrano<3,4-e>-1,3-oxazin-4-yl>-4-methyl-2,4-pentadienyl ester

There total 22 articles about <4R-<4α(2E,4E),4aβ,7α(2S*,3E),8β,8aβ>>-1H-imidazole-1-carboxylic acid 5--3-butenyl>-4a,8-dimethyl-2,5-dioxo-2H,5H-pyrano<3,4-e>-1,3-oxazin-4-yl>-4-methyl-2,4-pentadienyl 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:

: 2746-25-0
p-Methoxybenzyl bromide

: 152453-83-3
<4R-<4α(2E,4E),4aβ,7α(2S*,3E),8β,8aβ>>-1H-imidazole-1-carboxylic acid 5--3-butenyl>-4a,8-dimethyl-2,5-dioxo-2H,5H-pyrano<3,4-e>-1,3-oxazin-4-yl>-4-methyl-2,4-pentadienyl ester

Guidance literature:: Multi-step reaction with 16 steps

1: 1.) NaH / 1.) DMF, RT, 3 h, 2.) DMF, RT, 45 min

2: 77 percent / CaCO₃, HgCl₂ / acetonitrile; H₂O / 0.83 h / Ambient temperature

3: 1.) BF₃*Et₂O, 2.) a) 3 M aq. NaOH, b) 30percent aq. H₂O₂ / 1.) THF, hexane, -78 deg C, 1.5 h, 2.) THF, hexane, a) from -78 deg C to RT

4: 84 percent / imidazole / dimethylformamide / 48 h / Ambient temperature

5: 1.) Sudan III, oxygen-ozone, 2.) Me₂S / 1.) CH₂Cl₂, MeOH, -78 deg C, 2.) CH₂Cl₂, MeOH, from -78 deg C to RT

6: aq. NaH₂PO₄, aq. NaClO₂ / acetonitrile; dimethylsulfoxide / 2 h / Ambient temperature

7: 87 percent / diethyl ether / 0.25 h / 0 °C

8: 97 percent / CuCl₂*2H₂O / methanol / 1 h / Heating

9: Pb(OAc)4 / tetrahydrofuran / 0.67 h / 0 °C

10: CrCl₂ / tetrahydrofuran / 1 h / sonication

11: 75 percent / LiOH / tetrahydrofuran; H₂O; methanol / 12 h / Ambient temperature

12: 89 percent / Ph₃P / tetrahydrofuran / 15 h / Ambient temperature

13: 1.) LDA / 1.) THF, -78 deg C, 20 min, 2.) THF, -78 deg C, 10 min

14: 85 percent / potassium triethylborohydride / diethyl ether / 0.17 h / -78 °C

15: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

16: 1.) methanesulfonic acid, 2.) triethylamine / 1.) THF, RT, 2 h, 2.) THF, RT, 12 h

With 1H-imidazole; chromium dichloride; lead(IV) acetate; lithium hydroxide; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; methanesulfonic acid; dimethylsulfide; oil scarlet; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; dihydrogen peroxide; oxygen; sodium hydride; potassium triethylborohydride; ozone; triethylamine; triphenylphosphine; calcium carbonate; mercury dichloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja00136a025

Reference yield:

: 166186-07-8
(S)-1-(tert-Butyl-dimethyl-silanyl)-4-[(1E,3E)-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-penta-1,3-dienyl]-azetidin-2-one

: 152453-83-3
<4R-<4α(2E,4E),4aβ,7α(2S*,3E),8β,8aβ>>-1H-imidazole-1-carboxylic acid 5--3-butenyl>-4a,8-dimethyl-2,5-dioxo-2H,5H-pyrano<3,4-e>-1,3-oxazin-4-yl>-4-methyl-2,4-pentadienyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) LDA / 1.) THF, -78 deg C

2: 1.) LDA / 1.) THF, -78 deg C, 20 min, 2.) THF, -78 deg C, 10 min

3: 85 percent / potassium triethylborohydride / diethyl ether / 0.17 h / -78 °C

4: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

5: 1.) methanesulfonic acid, 2.) triethylamine / 1.) THF, RT, 2 h, 2.) THF, RT, 12 h

With methanesulfonic acid; tetrabutyl ammonium fluoride; potassium triethylborohydride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether;
DOI:10.1021/ja00136a025

Reference yield:

: 133589-71-6
(4S,1'E)-4-(3'-hydroxy-2'-methylprop-1'-enyl)azetidin-2-one

: 152453-83-3
<4R-<4α(2E,4E),4aβ,7α(2S*,3E),8β,8aβ>>-1H-imidazole-1-carboxylic acid 5--3-butenyl>-4a,8-dimethyl-2,5-dioxo-2H,5H-pyrano<3,4-e>-1,3-oxazin-4-yl>-4-methyl-2,4-pentadienyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 86 percent / (COCl)2, DMSO / CH₂Cl₂

2: toluene / 1 h / 50 °C

3: diisobutylaluminum hydride / tetrahydrofuran / -78 - 0 °C

4: Et₃N / CH₂Cl₂

5: 1.) LDA / 1.) THF, -78 deg C

6: 1.) LDA / 1.) THF, -78 deg C, 20 min, 2.) THF, -78 deg C, 10 min

7: 85 percent / potassium triethylborohydride / diethyl ether / 0.17 h / -78 °C

8: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

9: 1.) methanesulfonic acid, 2.) triethylamine / 1.) THF, RT, 2 h, 2.) THF, RT, 12 h

With oxalyl dichloride; methanesulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; potassium triethylborohydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1021/ja00136a025