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

Base Information

Chemical Name:Benzoic acid (2S,3R,4R,5S,6R)-3-azido-4-benzyloxy-6-benzyloxymethyl-5-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl ester
CAS No.:918948-12-6
Molecular Formula:C₃₈H₃₅N₃O₆
Molecular Weight:629.712
Hs Code.:

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

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

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

There total 5 articles about Benzoic acid (2S,3R,4R,5S,6R)-3-azido-4-benzyloxy-6-benzyloxymethyl-5-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-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: 91.0%

: 918948-12-6
Benzoic acid (2S,3R,4R,5S,6R)-3-azido-4-benzyloxy-6-benzyloxymethyl-5-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl ester

Guidance literature:

Reference yield:

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

: 918948-12-6
Benzoic acid (2S,3R,4R,5S,6R)-3-azido-4-benzyloxy-6-benzyloxymethyl-5-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 86 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

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

Reference yield:

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

: 918948-12-6
Benzoic acid (2S,3R,4R,5S,6R)-3-azido-4-benzyloxy-6-benzyloxymethyl-5-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-2-yl ester

Guidance literature:: Multi-step reaction with 4 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: triethylamine / CH₂Cl₂ / 8 h / 20 °C

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

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