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

Base Information

• Chemical Name: methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-β-L-idopyranosyluronate trichloroacetimidate
• CAS No.: 444118-87-0
• Molecular Formula: C₂₄H₃₄Cl₃NO₈Si
• Molecular Weight: 598.98

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

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

Chemical Property:

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

There total 19 articles about methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-β-L-idopyranosyluronate trichloroacetimidate 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: 92.0%

trichloroacetonitrile (545-06-2) + methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-L-idopyranosyluronate → methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-β-L-idopyranosyluronate trichloroacetimidate (444118-87-0)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; 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 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-β-L-idopyranosyluronate trichloroacetimidate (444118-87-0)

Guidance literature:

Multi-step reaction with 16 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

13: 92 percent / aq. dichloroacetic acid / 3 h / 20 °C

14: 98 percent / pyridine; DMAP / CH₂Cl₂ / 6 h / 20 °C

15: 75 percent / BnNH₂ / diethyl ether / 6 h

16: 92 percent / DBU / CH₂Cl₂ / 1 h / 0 °C

With pyridine; 2,6-dimethylpyridine; dichloro-acetic acid; dmap; sodium hydroxide; sodium hypochlorite; sodium hydrogencarbonate; potassium hydrogencarbonate; pyridine hydrogenfluoride; hydrazine hydrate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; (+)-10-camphorsulfonic acid; benzylamine; trifluoroacetic acid; potassium bromide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; tetrabutylammomium bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/chem.200390009

Reference yield:

benzyl bromide (100-39-0) → methyl 2-O-acetyl-3-O-benzyl-4-O-tert-butyldimethylsilyl-β-L-idopyranosyluronate trichloroacetimidate (444118-87-0)

Guidance literature:

Multi-step reaction with 18 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

15.1: 92 percent / aq. dichloroacetic acid / 3 h / 20 °C

16.1: 98 percent / pyridine; DMAP / CH₂Cl₂ / 6 h / 20 °C

17.1: 75 percent / BnNH₂ / diethyl ether / 6 h

18.1: 92 percent / DBU / CH₂Cl₂ / 1 h / 0 °C

With pyridine; 2,6-dimethylpyridine; dichloro-acetic acid; dmap; sodium hydroxide; sodium hypochlorite; sodium hydride; sodium hydrogencarbonate; potassium hydrogencarbonate; pyridine hydrogenfluoride; hydrazine hydrate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; (+)-10-camphorsulfonic acid; benzylamine; trifluoroacetic acid; potassium bromide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; tetrabutylammomium bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/chem.200390009

upstream raw materials:

trichloroacetonitrile

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

benzyl bromide

3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose

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

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