methyl 3-O-benzyl-4-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-β-L-idopyranosyluronate

Base Information

• Chemical Name: methyl 3-O-benzyl-4-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-β-L-idopyranosyluronate
• CAS No.: 444119-08-8
• Molecular Formula: C₂₃H₃₆O₇Si
• Molecular Weight: 452.62
• Mol file: 444119-08-8.mol

Synonyms:methyl 3-O-benzyl-4-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-β-L-idopyranosyluronate

Chemical Property of methyl 3-O-benzyl-4-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-β-L-idopyranosyluronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-O-benzyl-4-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-β-L-idopyranosyluronate

There total 16 articles about methyl 3-O-benzyl-4-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-β-L-idopyranosyluronate 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: 98.0%

t-butyldimethylsiyl triflate (69739-34-0) + 1,2-O-isopropylidene-3-O-benzyl-4-O-trichloroacetyl-6-methyl-α-L-idonic acid (444118-44-9) → methyl 3-O-benzyl-4-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-β-L-idopyranosyluronate (444119-08-8)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃; for 1h;

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) → methyl 3-O-benzyl-4-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-β-L-idopyranosyluronate (444119-08-8)

Guidance literature:

Multi-step reaction with 12 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

9: N₂H₄*H₂O; pyridine; AcOH / 0.25 h

10: 8.0 g / aq. TFA / 0.25 h

11: 68 percent / (1S)-(+)-camphorsulfonic acid / dimethylformamide / 6 h / 0 °C

12: 98 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

With pyridine; 2,6-dimethylpyridine; dmap; sodium hydroxide; sodium hypochlorite; sodium hydrogencarbonate; potassium hydrogencarbonate; pyridine hydrogenfluoride; hydrazine hydrate; acetic acid; (+)-10-camphorsulfonic acid; trifluoroacetic 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:

benzyl bromide (100-39-0) → methyl 3-O-benzyl-4-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-β-L-idopyranosyluronate (444119-08-8)

Guidance literature:

Multi-step reaction with 14 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

11.1: N₂H₄*H₂O; pyridine; AcOH / 0.25 h

12.1: 8.0 g / aq. TFA / 0.25 h

13.1: 68 percent / (1S)-(+)-camphorsulfonic acid / dimethylformamide / 6 h / 0 °C

14.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

With pyridine; 2,6-dimethylpyridine; dmap; sodium hydroxide; sodium hypochlorite; sodium hydride; sodium hydrogencarbonate; potassium hydrogencarbonate; pyridine hydrogenfluoride; hydrazine hydrate; acetic acid; (+)-10-camphorsulfonic acid; trifluoroacetic 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:

t-butyldimethylsiyl triflate

1,2-O-isopropylidene-3-O-benzyl-4-O-trichloroacetyl-6-methyl-α-L-idonic acid

(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:

methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-β-L-idopyranosyluronate trichloroacetimidate

methyl 1,2-di-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-α/β-L-idopyranosyluronate

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

Refernces