pent-4-enyl (6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate

Base Information

• Chemical Name: pent-4-enyl (6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate
• CAS No.: 444118-75-6
• Molecular Formula: C₄₅H₆₃N₃O₁₄Si
• Molecular Weight: 898.092

Synonyms:pent-4-enyl (6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate

Chemical Property of pent-4-enyl (6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of pent-4-enyl (6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate

There total 20 articles about pent-4-enyl (6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate 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: 75.0%

n-Pent-4-enyl alcohol (821-09-0) + 6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 2-O-levulinoyl-3-O-benzyl-α-D-glucopyranosyluronate trichloroacetimidate (444118-67-6) → pent-4-enyl (6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate (444118-75-6)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In toluene; at 0 - 20 ℃; for 2h;

DOI:10.1002/chem.200390009

Reference yield:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) → pent-4-enyl (6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate (444118-75-6)

Guidance literature:

Multi-step reaction with 15 steps

1: pyridine; DMAP / CH₂Cl₂ / 19 h / 20 °C

2: pyridine; DMAP / 20 °C

3: HF*pyridine; pyridine / tetrahydrofuran / 20 °C

4: NaOCl; aq. NaHCO₃; KBr / TEMPO; Bu₄NBr / CH₂Cl₂ / 0.5 h

5: aq. NaOH / methanol / 20 °C

6: 44 g / KHCO₃ / dimethylformamide / 20 °C

7: 100 percent / aq. TFA / 0.25 h / 20 °C

8: 48 percent / (1S)-(+)-camphorsulfonic acid / dimethylformamide / 0 - 20 °C

9: 80 percent / molecular sieves 4 Angstroem; AgClO₄; SnCl₂ / diethyl ether / 23.5 h / 0 - 12 °C

10: 81 percent / aq. dichloroacetic acid / 1 h / 20 °C

11: 84 percent / imidazole / CH₂Cl₂ / 40 h

12: 97 percent / DMAP / CH₂Cl₂ / 2 h / 20 °C

13: glacial AcOH; TBAF / tetrahydrofuran / 0.5 h

14: 1.0 g / DBU / CH₂Cl₂ / 4 h / 0 - 20 °C

15: 75 percent / TMSOTf / toluene / 2 h / 0 - 20 °C

With pyridine; 1H-imidazole; dichloro-acetic acid; dmap; sodium hydroxide; sodium hypochlorite; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; silver perchlorate; sodium hydrogencarbonate; potassium hydrogencarbonate; pyridine hydrogenfluoride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; (+)-10-camphorsulfonic acid; trifluoroacetic acid; tin(ll) chloride; potassium bromide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; tetrabutylammomium bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1002/chem.200390009

Reference yield:

3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose (18685-18-2) → pent-4-enyl (6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate (444118-75-6)

Guidance literature:

Multi-step reaction with 16 steps

1: aq. AcOH / 20 h / 20 - 40 °C

2: pyridine; DMAP / CH₂Cl₂ / 19 h / 20 °C

3: pyridine; DMAP / 20 °C

4: HF*pyridine; pyridine / tetrahydrofuran / 20 °C

5: NaOCl; aq. NaHCO₃; KBr / TEMPO; Bu₄NBr / CH₂Cl₂ / 0.5 h

6: aq. NaOH / methanol / 20 °C

7: 44 g / KHCO₃ / dimethylformamide / 20 °C

8: 100 percent / aq. TFA / 0.25 h / 20 °C

9: 48 percent / (1S)-(+)-camphorsulfonic acid / dimethylformamide / 0 - 20 °C

10: 80 percent / molecular sieves 4 Angstroem; AgClO₄; SnCl₂ / diethyl ether / 23.5 h / 0 - 12 °C

11: 81 percent / aq. dichloroacetic acid / 1 h / 20 °C

12: 84 percent / imidazole / CH₂Cl₂ / 40 h

13: 97 percent / DMAP / CH₂Cl₂ / 2 h / 20 °C

14: glacial AcOH; TBAF / tetrahydrofuran / 0.5 h

15: 1.0 g / DBU / CH₂Cl₂ / 4 h / 0 - 20 °C

16: 75 percent / TMSOTf / toluene / 2 h / 0 - 20 °C

With pyridine; 1H-imidazole; dichloro-acetic acid; dmap; sodium hydroxide; sodium hypochlorite; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; silver perchlorate; sodium hydrogencarbonate; potassium hydrogencarbonate; pyridine hydrogenfluoride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; (+)-10-camphorsulfonic acid; trifluoroacetic acid; tin(ll) chloride; potassium bromide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; tetrabutylammomium bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1002/chem.200390009

upstream raw materials:

n-Pent-4-enyl alcohol

6-O-acetyl-2-azido-3-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 2-O-levulinoyl-3-O-benzyl-α-D-glucopyranosyluronate trichloroacetimidate

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

benzyl bromide

Downstream raw materials:

pent-4-enyl (methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-(1->4)-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate

pent-4-enyl (methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α-L-idopyranosyluronate)-(1->4)-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate

pent-4-enyl (6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyluronate

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