Acetic acid (2R,3R,4S,5R,6R)-3,5-bis-benzyloxy-2-(3,5-dinitro-pyridin-2-yloxy)-6-methyl-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5R,6R)-3,5-bis-benzyloxy-2-(3,5-dinitro-pyridin-2-yloxy)-6-methyl-tetrahydro-pyran-4-yl ester
• CAS No.: 134311-95-8
• Molecular Formula: C₂₇H₂₇N₃O₁₀
• Molecular Weight: 553.525

Synonyms:Acetic acid (2R,3R,4S,5R,6R)-3,5-bis-benzyloxy-2-(3,5-dinitro-pyridin-2-yloxy)-6-methyl-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2R,3R,4S,5R,6R)-3,5-bis-benzyloxy-2-(3,5-dinitro-pyridin-2-yloxy)-6-methyl-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3R,4S,5R,6R)-3,5-bis-benzyloxy-2-(3,5-dinitro-pyridin-2-yloxy)-6-methyl-tetrahydro-pyran-4-yl ester

There total 15 articles about Acetic acid (2R,3R,4S,5R,6R)-3,5-bis-benzyloxy-2-(3,5-dinitro-pyridin-2-yloxy)-6-methyl-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: 38.0%

2-chloro-3,5-dinitropyridine (2578-45-2) + 3-O-acetyl-2,4-di-O-benzyl-6-deoxy-D-glucopyranose (127874-89-9,127875-08-5,127875-56-3,127880-30-2,134311-50-5,134311-88-9) → Acetic acid (2R,3R,4S,5R,6R)-3,5-bis-benzyloxy-2-(3,5-dinitro-pyridin-2-yloxy)-6-methyl-tetrahydro-pyran-4-yl ester (134311-95-8) + Acetic acid (2S,3R,4S,5R,6R)-3,5-bis-benzyloxy-2-(3,5-dinitro-pyridin-2-yloxy)-6-methyl-tetrahydro-pyran-4-yl ester (134311-64-1)

Guidance literature:

With potassium fluoride; 18-crown-6 ether; triethylamine; In tetrahydrofuran; for 3h; Ambient temperature;

Reference yield:

(3aR,5R,6S,6aR)-6-(allyloxy)-5-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole (20316-77-2) → Acetic acid (2R,3R,4S,5R,6R)-3,5-bis-benzyloxy-2-(3,5-dinitro-pyridin-2-yloxy)-6-methyl-tetrahydro-pyran-4-yl ester (134311-95-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 95 percent / 2 N H₂SO₄ / methanol / 20 h / Ambient temperature

2: 89 percent / DMAP / CH₂Cl₂; pyridine / 96 h / Ambient temperature

3: 86 percent / LiAlH₄ / tetrahydrofuran / 8 h / Ambient temperature

4: 92 percent / 0.35 M HCl / 96 h / Ambient temperature

5: 33 percent / KH / tetrahydrofuran / 2 h / Ambient temperature

6: t-BuOK / dimethylsulfoxide / 0.33 h / 100 °C

7: 2 N H₂SO₄ / tetrahydrofuran / 24 h / Ambient temperature

8: 95 percent / DMAP / pyridine / 0.33 h / Ambient temperature

9: 89 percent / SOCl₂, AcCl / 16 h / 45 °C

10: 98 percent / H₂O, Ag₂O, BaCO₃ / acetonitrile / 4 h / 45 °C

11: 36 percent / KF, 18-crown-6, Et₃N / tetrahydrofuran / 3 h / Ambient temperature

With hydrogenchloride; dmap; potassium fluoride; lithium aluminium tetrahydride; thionyl chloride; 18-crown-6 ether; sulfuric acid; potassium tert-butylate; water; potassium hydride; triethylamine; acetyl chloride; barium carbonate; silver(l) oxide; In tetrahydrofuran; pyridine; methanol; dichloromethane; dimethyl sulfoxide; acetonitrile;

Reference yield:

(3R,4S,5R,6R)-4-Allyloxy-2-methoxy-6-methyl-tetrahydro-pyran-3,5-diol (134311-54-9,134311-90-3,135041-29-1,135041-32-6,141942-11-2) → Acetic acid (2R,3R,4S,5R,6R)-3,5-bis-benzyloxy-2-(3,5-dinitro-pyridin-2-yloxy)-6-methyl-tetrahydro-pyran-4-yl ester (134311-95-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 33 percent / KH / tetrahydrofuran / 2 h / Ambient temperature

2: t-BuOK / dimethylsulfoxide / 0.33 h / 100 °C

3: 2 N H₂SO₄ / tetrahydrofuran / 24 h / Ambient temperature

4: 95 percent / DMAP / pyridine / 0.33 h / Ambient temperature

5: 89 percent / SOCl₂, AcCl / 16 h / 45 °C

6: 98 percent / H₂O, Ag₂O, BaCO₃ / acetonitrile / 4 h / 45 °C

7: 36 percent / KF, 18-crown-6, Et₃N / tetrahydrofuran / 3 h / Ambient temperature

With dmap; potassium fluoride; thionyl chloride; 18-crown-6 ether; sulfuric acid; potassium tert-butylate; water; potassium hydride; triethylamine; acetyl chloride; barium carbonate; silver(l) oxide; In tetrahydrofuran; pyridine; dimethyl sulfoxide; acetonitrile;

upstream raw materials:

2-chloro-3,5-dinitropyridine

3-O-acetyl-2,4-di-O-benzyl-6-deoxy-D-glucopyranose

(3aR,5R,6S,6aR)-6-(allyloxy)-5-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole

(3R,4S,5R,6R)-4-Allyloxy-2-methoxy-6-methyl-tetrahydro-pyran-3,5-diol

Downstream raw materials:

C₄₉H₇₀O₆

C₄₉H₇₀O₆

Acetic acid (2S,3R,4S,5R,6R)-3-((2R,3R,4S,5R,6R)-4-acetoxy-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-allyloxy-5-benzyloxy-6-methyl-tetrahydro-pyran-4-yl ester

Acetic acid (2R,3R,4S,5R,6R)-3-((2S,3R,4S,5R,6R)-4-acetoxy-3,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-allyloxy-5-benzyloxy-6-methyl-tetrahydro-pyran-4-yl ester

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