6-(2-azido-3-O-benzyl-2-deoxy-5-O-benzoyl-4-C-(benzoyloxymethyl)-β-D-erythro-pentofuranosyl)-tetrazolo[1,5-c]pyrimidin-8-methyl-5(6H)-one

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Chemical Name:6-(2-azido-3-O-benzyl-2-deoxy-5-O-benzoyl-4-C-(benzoyloxymethyl)-β-D-erythro-pentofuranosyl)-tetrazolo[1,5-c]pyrimidin-8-methyl-5(6H)-one
CAS No.:552856-61-8
Molecular Formula:C₃₂H₂₈N₈O₇
Molecular Weight:636.624
Hs Code.:

Synonyms:6-(2-azido-3-O-benzyl-2-deoxy-5-O-benzoyl-4-C-(benzoyloxymethyl)-β-D-erythro-pentofuranosyl)-tetrazolo[1,5-c]pyrimidin-8-methyl-5(6H)-one

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Chemical Property of 6-(2-azido-3-O-benzyl-2-deoxy-5-O-benzoyl-4-C-(benzoyloxymethyl)-β-D-erythro-pentofuranosyl)-tetrazolo[1,5-c]pyrimidin-8-methyl-5(6H)-one

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Technology Process of 6-(2-azido-3-O-benzyl-2-deoxy-5-O-benzoyl-4-C-(benzoyloxymethyl)-β-D-erythro-pentofuranosyl)-tetrazolo[1,5-c]pyrimidin-8-methyl-5(6H)-one

There total 9 articles about 6-(2-azido-3-O-benzyl-2-deoxy-5-O-benzoyl-4-C-(benzoyloxymethyl)-β-D-erythro-pentofuranosyl)-tetrazolo[1,5-c]pyrimidin-8-methyl-5(6H)-one 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: 37.0%

: 552856-59-4
1-(3-O-benzyl-5-O-benzoyl-4-C-benzoyloxymethyl-β-D-threo-pentofuranosyl)thymine

: 1-(2-azido-3-O-benzyl-2-deoxy-5-O-benzoyl-4-C-(benzoyloxymethyl)-β-D-erythro-pentofuranosyl)thymine

: 552856-61-8
6-(2-azido-3-O-benzyl-2-deoxy-5-O-benzoyl-4-C-(benzoyloxymethyl)-β-D-erythro-pentofuranosyl)-tetrazolo[1,5-c]pyrimidin-8-methyl-5(6H)-one

Guidance literature:: 1-(3-O-benzyl-5-O-benzoyl-4-C-benzoyloxymethyl-β-D-threo-pentofuranosyl)thymine; With pyridine; trifluoroacetic anhydride; In dichloromethane; at 0 - 7 ℃; for 73h;

With sodium azide; In N,N-dimethyl-formamide; at 20 - 80 ℃; for 18.5h; Further stages.;
DOI:10.1039/b208864a

Reference yield:

: 552856-54-9
1,2-di-O-acetyl-5-O-benzoyl-4-C-benzoyloxymethyl-3-O-benzyl-D-erythro-pentofuranose

: 552856-61-8
6-(2-azido-3-O-benzyl-2-deoxy-5-O-benzoyl-4-C-(benzoyloxymethyl)-β-D-erythro-pentofuranosyl)-tetrazolo[1,5-c]pyrimidin-8-methyl-5(6H)-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 1 h / 0 °C

1.2: trimethylsilyl triflate / acetonitrile / 2 h / 65 °C

2.1: 84 percent / methanolic ammonia / methanol / 0 - 20 °C

3.1: pyridine / CH₂Cl₂ / 0 - 20 °C

4.1: 98 percent / DBU / dimethylformamide / 20 °C

5.1: 80 percent / aq. HCl / CH₂Cl₂ / 5 h / 80 °C

6.1: pyridine; trifluoroacetic anhydride / CH₂Cl₂ / 73 h / 0 - 7 °C

6.2: 25 percent / NaN₃ / dimethylformamide / 18.5 h / 20 - 80 °C

With pyridine; hydrogenchloride; N,O-bis-(trimethylsilyl)-acetamide; ammonia; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic anhydride; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1039/b208864a

Reference yield:

: 552856-52-7
5-O-benzoyl-4-C-benzoyloxymethyl-3-O-benzyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose

: 552856-61-8
6-(2-azido-3-O-benzyl-2-deoxy-5-O-benzoyl-4-C-(benzoyloxymethyl)-β-D-erythro-pentofuranosyl)-tetrazolo[1,5-c]pyrimidin-8-methyl-5(6H)-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: aq. H₂SO₄ / acetic acid / 18 h / 20 °C

2.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 1 h / 0 °C

2.2: trimethylsilyl triflate / acetonitrile / 2 h / 65 °C

3.1: 84 percent / methanolic ammonia / methanol / 0 - 20 °C

4.1: pyridine / CH₂Cl₂ / 0 - 20 °C

5.1: 98 percent / DBU / dimethylformamide / 20 °C

6.1: 80 percent / aq. HCl / CH₂Cl₂ / 5 h / 80 °C

7.1: pyridine; trifluoroacetic anhydride / CH₂Cl₂ / 73 h / 0 - 7 °C

7.2: 25 percent / NaN₃ / dimethylformamide / 18.5 h / 20 - 80 °C

With pyridine; hydrogenchloride; N,O-bis-(trimethylsilyl)-acetamide; sulfuric acid; ammonia; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic anhydride; In methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1039/b208864a