Methyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosylunorate)-(1->3)-2-acetamido-4-O-benzyl-2-deoxy-β-D-galactopyranoside

Base Information

• Chemical Name: Methyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosylunorate)-(1->3)-2-acetamido-4-O-benzyl-2-deoxy-β-D-galactopyranoside
• CAS No.: 303128-03-2
• Molecular Formula: C₄₄H₄₉NO₁₃
• Molecular Weight: 799.872
• Mol file: 303128-03-2.mol

Synonyms:Methyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosylunorate)-(1->3)-2-acetamido-4-O-benzyl-2-deoxy-β-D-galactopyranoside

Chemical Property of Methyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosylunorate)-(1->3)-2-acetamido-4-O-benzyl-2-deoxy-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosylunorate)-(1->3)-2-acetamido-4-O-benzyl-2-deoxy-β-D-galactopyranoside

There total 20 articles about Methyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosylunorate)-(1->3)-2-acetamido-4-O-benzyl-2-deoxy-β-D-galactopyranoside 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: 85.0%

Methyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyluronate)-(1->3)-2-acetamido-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-galactopyranoside (303128-01-0) → Methyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosylunorate)-(1->3)-2-acetamido-4-O-benzyl-2-deoxy-β-D-galactopyranoside (303128-03-2)

Guidance literature:

With acetic acid; In tetrahydrofuran; at 40 ℃; for 4h;

DOI:10.1039/b002835p

Reference yield:

Methyl 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside (56644-73-6) → Methyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosylunorate)-(1->3)-2-acetamido-4-O-benzyl-2-deoxy-β-D-galactopyranoside (303128-03-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: methanol / 16 h / 20 °C

2.1: 4.16 g / pyridine / CH₂Cl₂ / 1.3 h / 0 °C

3.1: pyridine / CH₂Cl₂ / 2 h / -15 - 0 °C

4.1: 3.33 g / NaNO₂ / dimethylformamide / 1.5 h / 20 °C

5.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

5.2: 80 percent / TBAI / tetrahydrofuran / 5 h / 0 - 20 °C

6.1: methanol

7.1: 3 g / imidazole / dimethylformamide / 0.67 h / 0 °C

8.1: 68 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂; toluene / 0.5 h / 20 °C

9.1: 82 percent / tributylstannane; azoisobutyronitrile / benzene / 1.5 h / 20 - 80 °C

10.1: 85 percent / aq. AcOH / tetrahydrofuran / 4 h / 40 °C

With pyridine; 1H-imidazole; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tri-n-butyl-tin hydride; sodium hydride; acetic acid; sodium nitrite; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 1.1: Deacetylation / 2.1: Acylation / 3.1: Substitution / 4.1: Substitution / 5.1: Metallation / 5.2: Etherification / 6.1: Substitution / 7.1: Substitution / 8.1: Substitution / 9.1: Reduction / 10.1: Hydrolysis;

DOI:10.1039/b002835p

Reference yield:

1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose (39686-94-7,56632-47-4,65827-58-9,99202-62-7,99202-66-1,103082-79-7,103703-00-0,103703-01-1,118711-49-2,127853-23-0,139563-66-9) → Methyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosylunorate)-(1->3)-2-acetamido-4-O-benzyl-2-deoxy-β-D-galactopyranoside (303128-03-2)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 69 percent / trimethylsilyl triflate; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 0 °C

2.1: 89 percent / methanol / 16 h / 20 °C

3.1: 84 percent / CF₃CO₂H / 0.33 h

4.1: 83 percent / pyridine / CH₂Cl₂ / 1.5 h / 0 - 20 °C

5.1: 64 percent / AlCl₃; borane-trimethylamine complex; 4 Angstroem molecular sieves / diethyl ether; CH₂Cl₂ / 2 h / 0 °C

6.1: 79 percent / CrO₃; H₂SO₄ / acetone / 1 h / 20 °C

7.1: 1.56 g / DMAP; Et₃N / CH₂Cl₂ / 2 h / 0 - 20 °C

8.1: cerium(IV) ammonium nitrite / H₂O; acetonitrile; toluene / 0.33 h / 20 °C

8.2: 71 percent / DBU / CH₂Cl₂ / 0.17 h / 0 °C

9.1: 68 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂; toluene / 0.5 h / 20 °C

10.1: 82 percent / tributylstannane; azoisobutyronitrile / benzene / 1.5 h / 20 - 80 °C

11.1: 85 percent / aq. AcOH / tetrahydrofuran / 4 h / 40 °C

With pyridine; chromium(VI) oxide; dmap; aluminium trichloride; ammonium cerium(IV) nitrate; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; trimethylamine-borane; 4 A molecular sieve; sulfuric acid; tri-n-butyl-tin hydride; acetic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone; toluene; acetonitrile; benzene; 1.1: Etherification / 2.1: Deacetylation / 3.1: Cyclization / 4.1: Acylation / 5.1: Ring cleavage / 6.1: Oxidation / 7.1: Acylation / 8.1: Substitution / 8.2: Addition / 9.1: Substitution / 10.1: Reduction / 11.1: Hydrolysis;

DOI:10.1039/b002835p

upstream raw materials:

Methyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyluronate)-(1->3)-2-acetamido-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-galactopyranoside

Methyl 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside

1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose

4-Methoxyphenyl 3-O-benzyl-β-D-glucopyranoside

Downstream raw materials:

(2S,3S,4R,5R,6R)-6-((2R,3R,4R,5R,6R)-3-Acetylamino-5-benzyloxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-4-yloxy)-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-carboxylic acid