methyl-2-acetamido-2-deoxyglucopyranosyl-1-4-glucopyranosiduronic acid

Base Information

• Chemical Name: methyl-2-acetamido-2-deoxyglucopyranosyl-1-4-glucopyranosiduronic acid
• CAS No.: 156881-25-3
• Molecular Formula: C₁₅H₂₅NO₁₂
• Molecular Weight: 411.363
• Mol file: 156881-25-3.mol

Synonyms:methyl-2-acetamido-2-deoxyglucopyranosyl-1-4-glucopyranosiduronic acid

Chemical Property of methyl-2-acetamido-2-deoxyglucopyranosyl-1-4-glucopyranosiduronic acid

Chemical Property:

• Vapor Pressure: 4.28E-30mmHg at 25°C
• Boiling Point: 806.4°Cat760mmHg
• Flash Point: 441.5°C
• Density: 1.61g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl-2-acetamido-2-deoxyglucopyranosyl-1-4-glucopyranosiduronic acid

There total 9 articles about methyl-2-acetamido-2-deoxyglucopyranosyl-1-4-glucopyranosiduronic 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:

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide (70831-94-6) → methyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1<*>4)-β-D-glucopyranosiduronic acid (156881-25-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) AgOTf, 3A MS, 2,4,6-collidine / 1.) CH₂Cl₂, RT, 1 h, 2.) CH₂Cl₂, RT, 4 h

2: CAN / acetonitrile; H₂O / 3.5 h

3: 1.) CrO₃, 3 M aq. H₂SO₄ / 1.) acetone, CH₂Cl₂, RT, 4 h, 2.) ether

4: 77 percent / H₂ / 30percent Pd/C / ethyl acetate; H₂O / 96 h / 2637.5 Torr

5: 1.) aq. NaOH, 2.) N₂H₄*H₂O

With 2,4,6-trimethyl-pyridine; chromium(VI) oxide; sodium hydroxide; ammonium cerium(IV) nitrate; sulfuric acid; hydrogen; silver trifluoromethanesulfonate; hydrazine hydrate; palladium on activated charcoal; In water; ethyl acetate; acetonitrile;

DOI:10.1016/0008-6215(94)84097-0

Reference yield:

methyl 2,3-di-O-benzyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranoside (152141-84-9) → methyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1<*>4)-β-D-glucopyranosiduronic acid (156881-25-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / CF₃CO₂H, 3A MS, NaBH₃CN / dimethylformamide / 17 h / Ambient temperature

2: 1.) AgOTf, 3A MS, 2,4,6-collidine / 1.) CH₂Cl₂, RT, 1 h, 2.) CH₂Cl₂, RT, 4 h

3: CAN / acetonitrile; H₂O / 3.5 h

4: 1.) CrO₃, 3 M aq. H₂SO₄ / 1.) acetone, CH₂Cl₂, RT, 4 h, 2.) ether

5: 77 percent / H₂ / 30percent Pd/C / ethyl acetate; H₂O / 96 h / 2637.5 Torr

6: 1.) aq. NaOH, 2.) N₂H₄*H₂O

With 2,4,6-trimethyl-pyridine; chromium(VI) oxide; sodium hydroxide; ammonium cerium(IV) nitrate; sulfuric acid; hydrogen; silver trifluoromethanesulfonate; sodium cyanoborohydride; hydrazine hydrate; trifluoroacetic acid; palladium on activated charcoal; In water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0008-6215(94)84097-0

Reference yield:

methyl 4,6-O-(4-methoxybenzylidene)-β-D-glucopyranoside (156928-37-9) → methyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1<*>4)-β-D-glucopyranosiduronic acid (156881-25-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) NaH / 1.) DMF, RT, 5 min, 2.) DMF, RT, 3 h

2: 84 percent / CF₃CO₂H, 3A MS, NaBH₃CN / dimethylformamide / 17 h / Ambient temperature

3: 1.) AgOTf, 3A MS, 2,4,6-collidine / 1.) CH₂Cl₂, RT, 1 h, 2.) CH₂Cl₂, RT, 4 h

4: CAN / acetonitrile; H₂O / 3.5 h

5: 1.) CrO₃, 3 M aq. H₂SO₄ / 1.) acetone, CH₂Cl₂, RT, 4 h, 2.) ether

6: 77 percent / H₂ / 30percent Pd/C / ethyl acetate; H₂O / 96 h / 2637.5 Torr

7: 1.) aq. NaOH, 2.) N₂H₄*H₂O

With 2,4,6-trimethyl-pyridine; chromium(VI) oxide; sodium hydroxide; ammonium cerium(IV) nitrate; sulfuric acid; hydrogen; silver trifluoromethanesulfonate; sodium hydride; sodium cyanoborohydride; hydrazine hydrate; trifluoroacetic acid; palladium on activated charcoal; In water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0008-6215(94)84097-0

upstream raw materials:

acetic anhydride

(2S,3S,4R,5R,6R)-3-[(2S,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-2-yloxy]-4,5-dihydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide

methyl 2,3-di-O-benzyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranoside

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