(1S,2S,3R,4R,5S)-4-(6-amino-9-purinyl)-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane

Base Information

Chemical Name:(1S,2S,3R,4R,5S)-4-(6-amino-9-purinyl)-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane
CAS No.:199122-63-9
Molecular Formula:C₂₇H₂₉N₅O₃
Molecular Weight:471.559
Hs Code.:

Synonyms:(1S,2S,3R,4R,5S)-4-(6-amino-9-purinyl)-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane

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Chemical Property of (1S,2S,3R,4R,5S)-4-(6-amino-9-purinyl)-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane

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Technology Process of (1S,2S,3R,4R,5S)-4-(6-amino-9-purinyl)-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane

There total 7 articles about (1S,2S,3R,4R,5S)-4-(6-amino-9-purinyl)-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: 50.0%

: 66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9
adenine

: 199122-49-1
(1S,2S,3R,4S,5S)-1,2-di<(benzyloxy)methyl>-3,4-sulfinyldioxybicyclo<3.1.0>hexane

: 199122-63-9
(1S,2S,3R,4R,5S)-4-(6-amino-9-purinyl)-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane

Guidance literature:: With 18-crown-6 ether; sodium hydride; In N,N-dimethyl-formamide; at 120 ℃; for 72h;
DOI:10.1016/0040-4039(96)00289-4

Reference yield:

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

: 199122-63-9
(1S,2S,3R,4R,5S)-4-(6-amino-9-purinyl)-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane

Guidance literature:: Multi-step reaction with 5 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: 50 percent / NaH, 18-crown-6 / dimethylformamide / 3 h / 80 °C

With hydrogenchloride; sodium perborate; thionyl chloride; borane-THF; 18-crown-6 ether; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo990010m

Reference yield:

: 199122-34-4
(1R,3R,4S,5S)-1-<(benzyloxy)methyl>-3,4-(isopropylidenedioxy)-2-oxo-bicyclo<3.1.0>hexane

: 199122-63-9
(1S,2S,3R,4R,5S)-4-(6-amino-9-purinyl)-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / n-BuLi / hexane; tetrahydrofuran / 0.5 h / 0 °C

2: 90 percent / BH₃*THF, NaBO₃*H₂O / tetrahydrofuran / 16 h / 0 - 20 °C

3: 88 percent / NaH, n-Bu₄NI / tetrahydrofuran / 15 h / Heating

4: 100 percent / aq. HCl / tetrahydrofuran; methanol / 10 h / Heating

5: 80 percent / SOCl₂, Et₃N / CH₂Cl₂ / 0.08 h / 0 °C

6: 50 percent / NaH, 18-crown-6 / dimethylformamide / 3 h / 80 °C

With hydrogenchloride; sodium perborate; n-butyllithium; thionyl chloride; borane-THF; 18-crown-6 ether; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo990010m