3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-azido-2-deoxy-α-D-glucopyranosyl nitrate

Base Information

• Chemical Name: 3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-azido-2-deoxy-α-D-glucopyranosyl nitrate
• CAS No.: 68733-14-2
• Molecular Formula: C₂₄H₃₂N₄O₁₈
• Molecular Weight: 664.534

Synonyms:

Chemical Property of 3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-azido-2-deoxy-α-D-glucopyranosyl nitrate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-azido-2-deoxy-α-D-glucopyranosyl nitrate

There total 1 articles about 3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-azido-2-deoxy-α-D-glucopyranosyl nitrate 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:

hexa-O-acetyl-D-lactal (51450-24-9) + 4-benzoylamino-1-(O2,O3-dibenzoyl-β-D-arabinofuranosyl)-1H-pyrimidin-2-one (15585-06-5) → 3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-azido-2-deoxy-α-D-glucopyranosyl nitrate (68733-14-2) + N4-benzoyl-1-[O-2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-O-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl-(1->5)-2,3-di-O-benzoyl-β-D-arabinofuranosyl]cytosine

Guidance literature:

hexa-O-acetyl-D-lactal; With sodium azide; ammonium cerium(IV) nitrate; In acetonitrile; at 20 ℃; for 24h;

With sodium acetate; acetic acid; at 100 ℃; for 2h;

4-benzoylamino-1-(O²,O³-dibenzoyl-β-D-arabinofuranosyl)-1H-pyrimidin-2-one; With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃;

DOI:10.1002/hlca.200390163

Reference yield:

3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-azido-2-deoxy-α-D-glucopyranosyl nitrate (68733-14-2) → 2,2,2-Trichloro-acetimidic acid (2R,3R,4R,5S,6R)-3-azido-4-benzyloxy-5-((3aS,4R,6S,7R,7aS)-7-benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester (213591-30-1)

Guidance literature:

Multi-step reaction with 7 steps

1: CaCO₃ / acetone; H₂O / 48 h / Ambient temperature

2: 92 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

3: 98 percent / NaOMe / methanol / 3 h / Ambient temperature

4: 66 percent / p-toluenesulfonic acid / 18 h / Ambient temperature

5: 78 percent / NaH / dimethylformamide / 16 h / -10 °C

6: tetrabutylammonium fluoride / CH₂Cl₂; tetrahydrofuran / 3 h / -20 °C

7: 99 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 2 h / -15 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; calcium carbonate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1002/(sici)1099-0690(199809)1998:9<1887::aid-ejoc1887>3.0.co;2-i

Reference yield:

3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-azido-2-deoxy-α-D-glucopyranosyl nitrate (68733-14-2) → (2S,3R,4S,5S,6R)-2-(((2R,3S,4R,5R,6S)-4-acetoxy-2-(acetoxymethyl)-5-azido-6-((tertbutyldiphenylsilyl)oxy)tetrahydro-2H-pyran-3-yl)oxy)-6-(acetoxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (213591-31-2)

Guidance literature:

Multi-step reaction with 2 steps

1: CaCO₃ / acetone; H₂O / 48 h / Ambient temperature

2: 92 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

With 1H-imidazole; calcium carbonate; In water; N,N-dimethyl-formamide; acetone;

DOI:10.1002/(sici)1099-0690(199809)1998:9<1887::aid-ejoc1887>3.0.co;2-i

upstream raw materials:

hexa-O-acetyl-D-lactal

4-benzoylamino-1-(O²,O³-dibenzoyl-β-D-arabinofuranosyl)-1H-pyrimidin-2-one

Downstream raw materials:

(2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-5-Azido-6-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

(3aS,4R,6S,7R,7aR)-6-[(2R,3S,4R,5R,6S)-5-Azido-6-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol

2,2,2-Trichloro-acetimidic acid (2R,3R,4R,5S,6R)-3-azido-4-benzyloxy-5-((3aS,4R,6S,7R,7aS)-7-benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

(2S,3R,4S,5S,6R)-2-(((2R,3S,4R,5R,6S)-4-acetoxy-2-(acetoxymethyl)-5-azido-6-((tertbutyldiphenylsilyl)oxy)tetrahydro-2H-pyran-3-yl)oxy)-6-(acetoxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

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