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

Base Information

Chemical Name:Benzoic acid (2R,3S,4R,5R)-5-azido-4-benzyloxy-3-(naphthalen-2-ylmethoxy)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-ylmethyl ester
CAS No.:657395-19-2
Molecular Formula:C₃₃H₂₉Cl₃N₄O₆
Molecular Weight:683.975
Hs Code.:

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

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

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

There total 9 articles about Benzoic acid (2R,3S,4R,5R)-5-azido-4-benzyloxy-3-(naphthalen-2-ylmethoxy)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-ylmethyl 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: 98.0%

: 545-06-2
trichloroacetonitrile

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

: 657395-19-2
Benzoic acid (2R,3S,4R,5R)-5-azido-4-benzyloxy-3-(naphthalen-2-ylmethoxy)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: With potassium carbonate;
DOI:10.1002/jccs.200400175

Reference yield: 94.0%

: 657395-19-2
Benzoic acid (2R,3S,4R,5R)-5-azido-4-benzyloxy-3-(naphthalen-2-ylmethoxy)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:

Reference yield:

: (2R,4aR,7R,8R,8aS)-7-Azido-2-naphthalen-2-yl-hexahydro-pyrano[3,2-d][1,3]dioxine-6,8-diol

: 657395-19-2
Benzoic acid (2R,3S,4R,5R)-5-azido-4-benzyloxy-3-(naphthalen-2-ylmethoxy)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 92 percent / triethylamine; 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / cooling

2: 86 percent / borane/tetrahydrofuran complex; copper(II) trifluoromethanesulfonate / tetrahydrofuran / 20 °C

3: 92 percent / triethylamine; 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / cooling

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

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

With tetrahydrofuran; dmap; borane; ammonia; copper(II) bis(trifluoromethanesulfonate); potassium carbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ol062464t