(1S,2S,3R,4R,5S)-4-3-benzoyl-2,4-(1H)-dioxopyrimidin-1-yl>-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane

Base Information

Chemical Name:(1S,2S,3R,4R,5S)-4-3-benzoyl-2,4-(1H)-dioxopyrimidin-1-yl>-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane
CAS No.:228394-10-3
Molecular Formula:C₃₃H₃₂N₂O₆
Molecular Weight:552.627
Hs Code.:

(1S,2S,3R,4R,5S)-4-<N<sup>3</sup>-benzoyl-2,4-(1H)-dioxopyrimidin-1-yl>-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane

Synonyms:(1S,2S,3R,4R,5S)-4-3-benzoyl-2,4-(1H)-dioxopyrimidin-1-yl>-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane

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Chemical Property of (1S,2S,3R,4R,5S)-4-3-benzoyl-2,4-(1H)-dioxopyrimidin-1-yl>-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane

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Technology Process of (1S,2S,3R,4R,5S)-4-3-benzoyl-2,4-(1H)-dioxopyrimidin-1-yl>-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane

There total 18 articles about (1S,2S,3R,4R,5S)-4-3-benzoyl-2,4-(1H)-dioxopyrimidin-1-yl>-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane 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: 90.0%

: 228394-09-0
(1S,2S,3R,4S,5S)-4-3-benzoyl-2,4-(1H)-dioxopyrimidin-1-yl>-3-(tert-butyldimethylsilyloxy)-1,2-di<(benzyloxy)methyl>bicyclo<3.1.0>hexane

: 228394-10-3
(1S,2S,3R,4R,5S)-4-3-benzoyl-2,4-(1H)-dioxopyrimidin-1-yl>-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 3h; Ambient temperature;
DOI:10.1021/jo990010m

Reference yield:

: 156126-13-5
(1aR,1bR,4aS,5S,5aS)-1a-Benzyloxymethyl-3,3-dimethyl-hexahydro-2,4-dioxa-cyclopropa[a]pentalen-5-ol

: 228394-10-3
(1S,2S,3R,4R,5S)-4-3-benzoyl-2,4-(1H)-dioxopyrimidin-1-yl>-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane

Guidance literature:: Multi-step reaction with 14 steps

1: 57 percent / p-TsOH*H₂O / 2 h / Heating

2: 100 percent / TPAP, NMO, 4A MS / CH₂Cl₂ / 0.67 h / Ambient temperature

3: 90 percent / n-BuLi / hexane; tetrahydrofuran / 0.5 h / 0 °C

4: 90 percent / BH₃*THF, NaBO₃*H₂O / tetrahydrofuran / 16 h / 0 - 20 °C

5: 88 percent / NaH, n-Bu₄NI / tetrahydrofuran / 15 h / Heating

6: 100 percent / aq. HCl / tetrahydrofuran; methanol / 10 h / Heating

7: 80 percent / SOCl₂, Et₃N / CH₂Cl₂ / 0.08 h / 0 °C

8: 81 percent / NaN₃ / dimethylformamide / 10 h / 100 °C

9: 96 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

10: 100 percent / Lindlar catalyst / CH₂Cl₂ / Ambient temperature

11: 1.) / 1.) benzene, 10 deg C, 30 min, 2.) benzene, 10 deg C, 30 min

12: 39 percent / NH₄OH / dimethylformamide / 100 °C

13: 94 percent / pyridine / 70 °C

14: 90 percent / TBAF / tetrahydrofuran / 3 h / Ambient temperature

With pyridine; hydrogenchloride; sodium perborate; ammonium hydroxide; Lindlar's catalyst; n-butyllithium; thionyl chloride; sodium azide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; borane-THF; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo990010m

Reference yield:

: 199122-38-8
(1R,3R,4S,5S)-1-<(benzyloxy)methyl>-3,4-(isopropylidenedioxy)-2-C-methylenebicyclo<3.1.0>hexane

: 228394-10-3
(1S,2S,3R,4R,5S)-4-3-benzoyl-2,4-(1H)-dioxopyrimidin-1-yl>-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane

Guidance literature:: Multi-step reaction with 11 steps

1: 90 percent / BH₃*THF, NaBO₃*H₂O / tetrahydrofuran / 16 h / 0 - 20 °C

2: 88 percent / NaH, n-Bu₄NI / tetrahydrofuran / 15 h / Heating

3: 100 percent / aq. HCl / tetrahydrofuran; methanol / 10 h / Heating

4: 80 percent / SOCl₂, Et₃N / CH₂Cl₂ / 0.08 h / 0 °C

5: 81 percent / NaN₃ / dimethylformamide / 10 h / 100 °C

6: 96 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

7: 100 percent / Lindlar catalyst / CH₂Cl₂ / Ambient temperature

8: 1.) / 1.) benzene, 10 deg C, 30 min, 2.) benzene, 10 deg C, 30 min

9: 39 percent / NH₄OH / dimethylformamide / 100 °C

10: 94 percent / pyridine / 70 °C

11: 90 percent / TBAF / tetrahydrofuran / 3 h / Ambient temperature

With pyridine; hydrogenchloride; sodium perborate; ammonium hydroxide; Lindlar's catalyst; thionyl chloride; sodium azide; borane-THF; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo990010m