Benzoic acid (2R,3R,4R,5S)-4-azido-2-(6-chloro-purin-9-yl)-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester

Base Information

Chemical Name:Benzoic acid (2R,3R,4R,5S)-4-azido-2-(6-chloro-purin-9-yl)-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester
CAS No.:216976-72-6
Molecular Formula:C₁₉H₁₆ClN₇O₆
Molecular Weight:473.832
Hs Code.:

Synonyms:Benzoic acid (2R,3R,4R,5S)-4-azido-2-(6-chloro-purin-9-yl)-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester

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Chemical Property of Benzoic acid (2R,3R,4R,5S)-4-azido-2-(6-chloro-purin-9-yl)-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester

Chemical Property:

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Technology Process of Benzoic acid (2R,3R,4R,5S)-4-azido-2-(6-chloro-purin-9-yl)-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester

There total 8 articles about Benzoic acid (2R,3R,4R,5S)-4-azido-2-(6-chloro-purin-9-yl)-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-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:

: 87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2
D-Xylose

: 216976-72-6
Benzoic acid (2R,3R,4R,5S)-4-azido-2-(6-chloro-purin-9-yl)-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 70 percent / H₂SO₄ / 3 h / Ambient temperature

2: 60 percent / imidazole / pentane / 3 h / Ambient temperature

3: pyridine / CH₂Cl₂ / 0.25 h / -10 °C

4: 56 percent / NaN₃ / pyridine / 120 h / Ambient temperature

5: 95 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature

6: 88 percent / pyridine / 5 h / Ambient temperature

7: 1,) conc. H₂SO₄, 2.) pyridine, DMAP / 1.) 4 deg C, 6 d, 2.) room temperature, overnight

8: 1.) MSTFA, 2.) TMS-OTf / 1.) DCE, reflux, 30 min, 2.) DCE, 80 deg C, overnight

With pyridine; 1H-imidazole; dmap; sodium azide; trimethylsilyl trifluoromethanesulfonate; N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; sulfuric acid; tetrabutyl ammonium fluoride; In tetrahydrofuran; pyridine; dichloromethane; pentane;
DOI:10.1016/S0040-4020(98)00819-9

Reference yield:

: 20031-21-4
1,2-O-isopropylidene-α-D-xylose

: 216976-72-6
Benzoic acid (2R,3R,4R,5S)-4-azido-2-(6-chloro-purin-9-yl)-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 60 percent / imidazole / pentane / 3 h / Ambient temperature

2: pyridine / CH₂Cl₂ / 0.25 h / -10 °C

3: 56 percent / NaN₃ / pyridine / 120 h / Ambient temperature

4: 95 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature

5: 88 percent / pyridine / 5 h / Ambient temperature

6: 1,) conc. H₂SO₄, 2.) pyridine, DMAP / 1.) 4 deg C, 6 d, 2.) room temperature, overnight

7: 1.) MSTFA, 2.) TMS-OTf / 1.) DCE, reflux, 30 min, 2.) DCE, 80 deg C, overnight

With pyridine; 1H-imidazole; dmap; sodium azide; trimethylsilyl trifluoromethanesulfonate; N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; sulfuric acid; tetrabutyl ammonium fluoride; In tetrahydrofuran; pyridine; dichloromethane; pentane;
DOI:10.1016/S0040-4020(98)00819-9

Reference yield:

: 114861-14-2
1,2-O-isopropylidene-5-O-(t-butyldiphenylsilyl)-α-D-xylofuranose

: 216976-72-6
Benzoic acid (2R,3R,4R,5S)-4-azido-2-(6-chloro-purin-9-yl)-5-methoxycarbonyloxymethyl-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: pyridine / CH₂Cl₂ / 0.25 h / -10 °C

2: 56 percent / NaN₃ / pyridine / 120 h / Ambient temperature

3: 95 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature

4: 88 percent / pyridine / 5 h / Ambient temperature

5: 1,) conc. H₂SO₄, 2.) pyridine, DMAP / 1.) 4 deg C, 6 d, 2.) room temperature, overnight

6: 1.) MSTFA, 2.) TMS-OTf / 1.) DCE, reflux, 30 min, 2.) DCE, 80 deg C, overnight

With pyridine; dmap; sodium azide; trimethylsilyl trifluoromethanesulfonate; N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; sulfuric acid; tetrabutyl ammonium fluoride; In tetrahydrofuran; pyridine; dichloromethane;
DOI:10.1016/S0040-4020(98)00819-9