Benzoic acid (3R,4R,5S,6R)-3-azido-6-benzyloxymethyl-5-(naphthalen-2-ylmethoxy)-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester

Base Information

Chemical Name:Benzoic acid (3R,4R,5S,6R)-3-azido-6-benzyloxymethyl-5-(naphthalen-2-ylmethoxy)-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester
CAS No.:918948-14-8
Molecular Formula:C₃₃H₂₉Cl₃N₄O₆
Molecular Weight:683.975
Hs Code.:

Synonyms:Benzoic acid (3R,4R,5S,6R)-3-azido-6-benzyloxymethyl-5-(naphthalen-2-ylmethoxy)-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester

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Chemical Property of Benzoic acid (3R,4R,5S,6R)-3-azido-6-benzyloxymethyl-5-(naphthalen-2-ylmethoxy)-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester

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Technology Process of Benzoic acid (3R,4R,5S,6R)-3-azido-6-benzyloxymethyl-5-(naphthalen-2-ylmethoxy)-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester

There total 6 articles about Benzoic acid (3R,4R,5S,6R)-3-azido-6-benzyloxymethyl-5-(naphthalen-2-ylmethoxy)-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-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:

: Benzoic acid (3R,4R,5S,6R)-3-azido-6-benzyloxymethyl-2-hydroxy-5-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-4-yl ester

: 545-06-2
trichloroacetonitrile

: 918948-14-8
Benzoic acid (3R,4R,5S,6R)-3-azido-6-benzyloxymethyl-5-(naphthalen-2-ylmethoxy)-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester

Guidance literature:: With potassium carbonate; In dichloromethane; at 20 ℃; for 16h;
DOI:10.1021/ol062464t

Reference yield:

: 918948-06-8
2-azido-3-O-benzoyl-2-deoxy-4-O-(2-naphthylmethyl)-β-D-glucopyranosyl benzoate

: 918948-14-8
Benzoic acid (3R,4R,5S,6R)-3-azido-6-benzyloxymethyl-5-(naphthalen-2-ylmethoxy)-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: triethylamine / CH₂Cl₂ / 8 h / 20 °C

2: molecular sieves 3 Angstroem; triethylsilane; trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 3 h / cooling

3: ammonia / tetrahydrofuran; methanol / 8.5 h / 0 °C

4: potassium carbonate / CH₂Cl₂ / 16 h / 20 °C

With triethylsilane; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; ammonia; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ol062464t

Reference yield:

: 918948-03-5
2-azido-3-O-benzoyl-2-deoxy-4,6-O-(2-naphthylmethylidene)-β-D-glucopyranosyl benzoate

: 918948-14-8
Benzoic acid (3R,4R,5S,6R)-3-azido-6-benzyloxymethyl-5-(naphthalen-2-ylmethoxy)-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 89 percent / borane/tetrahydrofuran complex; copper(II) trifluoromethanesulfonate / tetrahydrofuran / 20 °C

2: triethylamine / CH₂Cl₂ / 8 h / 20 °C

3: molecular sieves 3 Angstroem; triethylsilane; trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 3 h / cooling

4: ammonia / tetrahydrofuran; methanol / 8.5 h / 0 °C

5: potassium carbonate / CH₂Cl₂ / 16 h / 20 °C

With tetrahydrofuran; triethylsilane; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; borane; ammonia; copper(II) bis(trifluoromethanesulfonate); potassium carbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ol062464t