methyl 3-O-benzyl-1,2-O-isopropylidene-5-O-levulinoyl-β-L-idofuranosyluronate

Base Information

• Chemical Name: methyl 3-O-benzyl-1,2-O-isopropylidene-5-O-levulinoyl-β-L-idofuranosyluronate
• CAS No.: 444118-40-5
• Molecular Formula: C₂₂H₂₈O₉
• Molecular Weight: 436.459
• Mol file: 444118-40-5.mol

Synonyms:methyl 3-O-benzyl-1,2-O-isopropylidene-5-O-levulinoyl-β-L-idofuranosyluronate

Chemical Property of methyl 3-O-benzyl-1,2-O-isopropylidene-5-O-levulinoyl-β-L-idofuranosyluronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-O-benzyl-1,2-O-isopropylidene-5-O-levulinoyl-β-L-idofuranosyluronate

There total 13 articles about methyl 3-O-benzyl-1,2-O-isopropylidene-5-O-levulinoyl-β-L-idofuranosyluronate 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:

(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) → methyl 3-O-benzyl-1,2-O-isopropylidene-5-O-levulinoyl-β-L-idofuranosyluronate (444118-40-5)

Guidance literature:

Multi-step reaction with 8 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: pyridine / CH₂Cl₂ / 1 h / -10 °C

8: 12.8 g / dimethylformamide / 80 °C

With pyridine; dmap; sodium hydroxide; sodium hypochlorite; sodium hydrogencarbonate; potassium hydrogencarbonate; pyridine hydrogenfluoride; potassium bromide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; tetrabutylammomium bromide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/chem.200390009

Reference yield:

benzyl bromide (100-39-0) → methyl 3-O-benzyl-1,2-O-isopropylidene-5-O-levulinoyl-β-L-idofuranosyluronate (444118-40-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: NaH / tetrahydrofuran

1.2: Bu₄NI / tetrahydrofuran / 10 h / 20 °C

2.1: aq. AcOH / 20 h / 20 - 40 °C

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

4.1: pyridine; DMAP / 20 °C

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

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

7.1: aq. NaOH / methanol / 20 °C

8.1: 44 g / KHCO₃ / dimethylformamide / 20 °C

9.1: pyridine / CH₂Cl₂ / 1 h / -10 °C

10.1: 12.8 g / dimethylformamide / 80 °C

With pyridine; dmap; sodium hydroxide; sodium hypochlorite; sodium hydride; sodium hydrogencarbonate; potassium hydrogencarbonate; pyridine hydrogenfluoride; acetic acid; potassium bromide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; tetrabutylammomium bromide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/chem.200390009

Reference yield:

3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose (18685-18-2) → methyl 3-O-benzyl-1,2-O-isopropylidene-5-O-levulinoyl-β-L-idofuranosyluronate (444118-40-5)

Guidance literature:

Multi-step reaction with 9 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: pyridine / CH₂Cl₂ / 1 h / -10 °C

9: 12.8 g / dimethylformamide / 80 °C

With pyridine; dmap; sodium hydroxide; sodium hypochlorite; sodium hydrogencarbonate; potassium hydrogencarbonate; pyridine hydrogenfluoride; acetic acid; potassium bromide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; tetrabutylammomium bromide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/chem.200390009

upstream raw materials:

levulinic acid Na-salt

(S)-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-trifluoromethanesulfonyloxy-acetic acid methyl ester

(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-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-4-O-levulinoyl-β-D-glucopyranosyl)-(1->4)-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyl)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranoside

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

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

Refernces

• 1、 Orgueira, Hernan A.,Bartolozzi, Alessandra,Schell, Peter,Litjens, Remy E. J. N.,Palmacci, Emma R.,Seeberger, Peter H.. "Modular synthesis of heparin oligosaccharides". . p. 140 - 169. Retrieved 2007/10/03.