methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosiduronate

Base Information

• Chemical Name: methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosiduronate
• CAS No.: 444118-41-6
• Molecular Formula: C₁₇H₂₂O₇
• Molecular Weight: 338.357
• Mol file: 444118-41-6.mol

Synonyms:methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosiduronate

Chemical Property of methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosiduronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosiduronate

There total 17 articles about methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosiduronate 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: 48.0%

2-Methoxypropene (116-11-0) + methyl 3-O-benzyl-D-glucopyranosyluronate → (S)-methyl 2-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-hydroxyacetate (87326-73-6) + methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosiduronate (444118-41-6)

Guidance literature:

With camphor-10-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1002/1521-3773(20020617)41:12<2128::AID-ANIE2128>3.0.CO;2-V

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-α-D-glucopyranosiduronate (444118-41-6)

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

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

With pyridine; dmap; sodium hydroxide; sodium hypochlorite; sodium hydrogencarbonate; potassium hydrogencarbonate; pyridine hydrogenfluoride; (+)-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-1,2-O-isopropylidene-α-D-glucopyranosiduronate (444118-41-6)

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

10.1: 48 percent / (1S)-(+)-camphorsulfonic acid / dimethylformamide / 0 - 20 °C

With pyridine; dmap; sodium hydroxide; sodium hypochlorite; sodium hydride; sodium hydrogencarbonate; potassium hydrogencarbonate; pyridine hydrogenfluoride; 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:

2-Methoxypropene

1,2-dideoxy-6-O-triisopropylsilyl-D-arabino-1-hexenopyranose

D-glucal

3-O-benzyl-6-O-triisopropylsilyl-D-glucal

Downstream raw materials:

6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosyluronate

2-azido-3,6-di-O-benzyl-2-deoxy-4-O-levulinoyl-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-isopropylidene-α-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

6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyl-(1->4)-(3,6-di-O-acetyl-2-azido-2-deoxy-α/β-D-glucopyranosyl trichloroacetimidate

Refernces

• 1、 Lohman, Gregory J. S.,Seeberger, Peter H.. "One-pot conversion of glycals to cis-1,2-isopropylidene-α-glycosides". . p. 7541 - 7543. Retrieved 2007/10/03.