Benzoic acid (2R,3R,4S,5R,6R)-4-azido-6-methoxy-2-(4-methoxy-benzyloxymethyl)-5-methoxycarbonylmethoxy-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3R,4S,5R,6R)-4-azido-6-methoxy-2-(4-methoxy-benzyloxymethyl)-5-methoxycarbonylmethoxy-tetrahydro-pyran-3-yl ester
• CAS No.: 251323-98-5
• Molecular Formula: C₂₅H₂₉N₃O₉
• Molecular Weight: 515.52

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about Benzoic acid (2R,3R,4S,5R,6R)-4-azido-6-methoxy-2-(4-methoxy-benzyloxymethyl)-5-methoxycarbonylmethoxy-tetrahydro-pyran-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:

methyl 3-azido-3-deoxy-β-D-glucopyranoside (65784-76-1) → Benzoic acid (2R,3R,4S,5R,6R)-4-azido-6-methoxy-2-(4-methoxy-benzyloxymethyl)-5-methoxycarbonylmethoxy-tetrahydro-pyran-3-yl ester (251323-98-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 68 percent / p-toluenesulfonic acid monohydrate / dimethylformamide / 4 h

2: 80 percent / Ag₂O; KI / dimethylformamide / 16 h

3: 22 percent / NaBH₃CN; Me₃SiCl; 3 Angstroem molecular sieves / acetonitrile / 4 h

4: pyridine / CH₂Cl₂ / 2 h / 0 °C

5: toluene / 1 h

With pyridine; chloro-trimethyl-silane; 3 A molecular sieve; sodium cyanoborohydride; toluene-4-sulfonic acid; potassium iodide; silver(l) oxide; In dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0960-894X(03)00384-6

Reference yield:

1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-α/β-gluco-hexopyranose (185114-94-7,155417-78-0) → Benzoic acid (2R,3R,4S,5R,6R)-4-azido-6-methoxy-2-(4-methoxy-benzyloxymethyl)-5-methoxycarbonylmethoxy-tetrahydro-pyran-3-yl ester (251323-98-5)

Guidance literature:

Multi-step reaction with 8 steps

1: Me₃SiBr; BiBr₃ / CH₂Cl₂ / 4 h

2: Ag₂O; CaSO₄ / CH₂Cl₂ / 1 h

3: MeONa; MeOH / 4 h

4: 68 percent / p-toluenesulfonic acid monohydrate / dimethylformamide / 4 h

5: 80 percent / Ag₂O; KI / dimethylformamide / 16 h

6: 22 percent / NaBH₃CN; Me₃SiCl; 3 Angstroem molecular sieves / acetonitrile / 4 h

7: pyridine / CH₂Cl₂ / 2 h / 0 °C

8: toluene / 1 h

With pyridine; methanol; calcium sulfate; chloro-trimethyl-silane; bismuth(III) bromide; trimethylsilyl bromide; 3 A molecular sieve; sodium methylate; sodium cyanoborohydride; toluene-4-sulfonic acid; potassium iodide; silver(l) oxide; In dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0960-894X(03)00384-6

Reference yield:

Acetic acid (2R,3S,4S,5R,6R)-5-acetoxy-2-acetoxymethyl-4-azido-6-bromo-tetrahydro-pyran-3-yl ester (132470-43-0) → Benzoic acid (2R,3R,4S,5R,6R)-4-azido-6-methoxy-2-(4-methoxy-benzyloxymethyl)-5-methoxycarbonylmethoxy-tetrahydro-pyran-3-yl ester (251323-98-5)

Guidance literature:

Multi-step reaction with 7 steps

1: Ag₂O; CaSO₄ / CH₂Cl₂ / 1 h

2: MeONa; MeOH / 4 h

3: 68 percent / p-toluenesulfonic acid monohydrate / dimethylformamide / 4 h

4: 80 percent / Ag₂O; KI / dimethylformamide / 16 h

5: 22 percent / NaBH₃CN; Me₃SiCl; 3 Angstroem molecular sieves / acetonitrile / 4 h

6: pyridine / CH₂Cl₂ / 2 h / 0 °C

7: toluene / 1 h

With pyridine; methanol; calcium sulfate; chloro-trimethyl-silane; 3 A molecular sieve; sodium methylate; sodium cyanoborohydride; toluene-4-sulfonic acid; potassium iodide; silver(l) oxide; In dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0960-894X(03)00384-6

upstream raw materials:

tetrabutylammonium benzoate

[(2R,3R,4R,5S,6R)-4-Azido-2-methoxy-6-(4-methoxy-benzyloxymethyl)-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-3-yloxy]-acetic acid methyl ester

methyl 3-azido-3-deoxy-β-D-glucopyranoside

1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-α/β-gluco-hexopyranose

Downstream raw materials:

Benzoic acid (2R,3R,4S,5R,6R)-4-azido-2-hydroxymethyl-6-methoxy-5-methoxycarbonylmethoxy-tetrahydro-pyran-3-yl ester

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