methyl 4-O-(2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-α-L-idopyranosiduronic acid

Base Information

• Chemical Name: methyl 4-O-(2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-α-L-idopyranosiduronic acid
• CAS No.: 676342-80-6
• Molecular Formula: C₂₇H₃₃N₃O₁₁
• Molecular Weight: 575.573

Synonyms:methyl 4-O-(2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-α-L-idopyranosiduronic acid

Chemical Property of methyl 4-O-(2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-α-L-idopyranosiduronic acid

Chemical Property:

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Technology Process of methyl 4-O-(2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-α-L-idopyranosiduronic acid

There total 20 articles about methyl 4-O-(2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-α-L-idopyranosiduronic acid 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:

(2R,3S,4S,5R,6R)-3-((2R,3R,4R,5S,6R)-3-Azido-4-benzoyloxy-6-benzoyloxymethyl-5-benzyloxy-tetrahydro-pyran-2-yloxy)-5-benzoyloxy-4-benzyloxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid (676342-88-4) → methyl 4-O-(2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-α-L-idopyranosiduronic acid (676342-80-6)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃;

DOI:10.1002/chem.200305096

Reference yield:

6-hydroxy-1,2:3,5-di-O-isopropylidene-α-D-glucofuranoside (81562-09-6) → methyl 4-O-(2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-α-L-idopyranosiduronic acid (676342-80-6)

Guidance literature:

Multi-step reaction with 14 steps

1: 88 percent / HCl / ethanol / 18 h / 95 °C

2: 98 percent / Et₃N / CH₂Cl₂ / 3.5 h / 20 °C

3: TMSOTf; 3 Angstroem molecular sieves / CH₂Cl₂ / 1 h / -78 °C

4: Et₃SiH / CH₂Cl₂ / 1 h

5: 181 mg / tetra-n-butylammonium fluoride / CH₂Cl₂; tetrahydrofuran / 1.5 h

6: 85 percent / pyridine / CH₂Cl₂ / 4 h / cooling

7: 58 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / -78 - 20 °C

8: 89 percent / CF₃COOH / 24 h / 20 °C

9: 82 percent / HBr; AcOH; Ac₂O / CH₂Cl₂ / 0.5 h / 20 °C

10: K₂CO₃; 4 Angstroem molecular sieves / CH₂Cl₂ / 8 h / -78 - 20 °C

11: 58 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / -78 - 20 °C

12: 85 percent / HCl / methanol / 5 h / 20 °C

13: 315 mg / CrO₃; H₂SO₄; celite / acetone / 0 °C

14: 133 mg / MeONa / methanol / 20 °C

With pyridine; chromium(VI) oxide; hydrogenchloride; triethylsilane; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 A molecular sieve; Celite; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen bromide; sodium methylate; acetic anhydride; potassium carbonate; acetic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetone; 13: Jones oxidation;

DOI:10.1002/chem.200305096

Reference yield:

6-deoxy-1,2:3,5-di-O-isopropylidene-α-D-xylo-hex-5-enofuranose (87357-54-8) → methyl 4-O-(2-azido-4-O-benzyl-2-deoxy-α-D-glucopyranosyl)-3-O-benzyl-α-L-idopyranosiduronic acid (676342-80-6)

Guidance literature:

Multi-step reaction with 15 steps

1.1: BH₃*THF / tetrahydrofuran / 3 h / 20 °C

1.2: 92 percent / aq. H₂O₂; NaOH / tetrahydrofuran

2.1: 88 percent / HCl / ethanol / 18 h / 95 °C

3.1: 98 percent / Et₃N / CH₂Cl₂ / 3.5 h / 20 °C

4.1: TMSOTf; 3 Angstroem molecular sieves / CH₂Cl₂ / 1 h / -78 °C

5.1: Et₃SiH / CH₂Cl₂ / 1 h

6.1: 181 mg / tetra-n-butylammonium fluoride / CH₂Cl₂; tetrahydrofuran / 1.5 h

7.1: 85 percent / pyridine / CH₂Cl₂ / 4 h / cooling

8.1: 58 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / -78 - 20 °C

9.1: 89 percent / CF₃COOH / 24 h / 20 °C

10.1: 82 percent / HBr; AcOH; Ac₂O / CH₂Cl₂ / 0.5 h / 20 °C

11.1: K₂CO₃; 4 Angstroem molecular sieves / CH₂Cl₂ / 8 h / -78 - 20 °C

12.1: 58 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / -78 - 20 °C

13.1: 85 percent / HCl / methanol / 5 h / 20 °C

14.1: 315 mg / CrO₃; H₂SO₄; celite / acetone / 0 °C

15.1: 133 mg / MeONa / methanol / 20 °C

With pyridine; chromium(VI) oxide; hydrogenchloride; triethylsilane; borane-THF; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 A molecular sieve; Celite; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen bromide; sodium methylate; acetic anhydride; potassium carbonate; acetic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetone; 14.1: Jones oxidation;

DOI:10.1002/chem.200305096

upstream raw materials:

(2R,3S,4S,5R,6R)-3-((2R,3R,4R,5S,6R)-3-Azido-4-benzoyloxy-6-benzoyloxymethyl-5-benzyloxy-tetrahydro-pyran-2-yloxy)-5-benzoyloxy-4-benzyloxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid

6-hydroxy-1,2:3,5-di-O-isopropylidene-α-D-glucofuranoside

6-deoxy-1,2:3,5-di-O-isopropylidene-α-D-xylo-hex-5-enofuranose

1,6-anhydro-β-L-idopyranose

Downstream raw materials:

methyl 4-O-(2-azido-4-O-benzyl-2-deoxy-3,6-di-O-sulfonato-α-D-glucopyranosyl)-3-O-benzyl-2-O-sulfonato-α-L-idopyranosiduronic acid

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