methyl 2-acetamido-4-O-acetyl-3-O-{2-acetamido-3-O-benzyl-4-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranosyl}-6-O-tert-butyldiphenylsilyl-2-deoxy-β-L-galactopyranoside

Base Information

• Chemical Name: methyl 2-acetamido-4-O-acetyl-3-O-{2-acetamido-3-O-benzyl-4-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranosyl}-6-O-tert-butyldiphenylsilyl-2-deoxy-β-L-galactopyranoside
• CAS No.: 849222-10-2
• Molecular Formula: C₇₀H₉₃N₃O₁₇Si₂
• Molecular Weight: 1304.69
• Mol file: 849222-10-2.mol

Synonyms:methyl 2-acetamido-4-O-acetyl-3-O-{2-acetamido-3-O-benzyl-4-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranosyl}-6-O-tert-butyldiphenylsilyl-2-deoxy-β-L-galactopyranoside

Chemical Property of methyl 2-acetamido-4-O-acetyl-3-O-{2-acetamido-3-O-benzyl-4-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranosyl}-6-O-tert-butyldiphenylsilyl-2-deoxy-β-L-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-acetamido-4-O-acetyl-3-O-{2-acetamido-3-O-benzyl-4-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranosyl}-6-O-tert-butyldiphenylsilyl-2-deoxy-β-L-galactopyranoside

There total 17 articles about methyl 2-acetamido-4-O-acetyl-3-O-{2-acetamido-3-O-benzyl-4-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranosyl}-6-O-tert-butyldiphenylsilyl-2-deoxy-β-L-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:

(2S,3S,4S,5S,6S)-5-Azido-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3,4-diol → methyl 2-acetamido-4-O-acetyl-3-O-{2-acetamido-3-O-benzyl-4-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranosyl}-6-O-tert-butyldiphenylsilyl-2-deoxy-β-L-galactopyranoside (849222-10-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.00 g / pyridine / 4 h

2: CSA / dimethylformamide / 1 h

3: 943 mg / aq. AcOH / 0.25 h

4: 53 percent / 1-benzenesulfinyl piperidine; tri-tert-butylpyrimidine; Tf₂O / 3 Angstroem molecular sieves / CH₂Cl₂ / -60 - 20 °C

5: 62 percent / CSA / tetrahydrofuran; methanol / 18 h

6: 72 percent / DMAP; pyridine / 6 h

7: 71 percent / 1-benzenesulfinyl piperidine; tri-tert-butylpyrimidine; Tf₂O / 3 Angstroem molecular sieves / CH₂Cl₂ / 2 h / -60 - -20 °C

8: ethylenediamine; 3 Angstroem molecular sieves / butan-1-ol / 12 h / 90 °C

9: 74 mg / pyridine / 3 h

10: Me₃P; H₂O / tetrahydrofuran / 72 h

11: 31 mg / pyridine / 16 h

With pyridine; dmap; 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,5-tri-tert-butylpyrimidine; 3 A molecular sieve; camphor-10-sulfonic acid; water; acetic acid; ethylenediamine; trimethylphosphane; 3 A molecular sieve; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; butan-1-ol;

DOI:10.1002/chem.200400862

Reference yield:

methyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-L-galactopyranoside (849222-01-1) → methyl 2-acetamido-4-O-acetyl-3-O-{2-acetamido-3-O-benzyl-4-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranosyl}-6-O-tert-butyldiphenylsilyl-2-deoxy-β-L-galactopyranoside (849222-10-2)

Guidance literature:

Multi-step reaction with 12 steps

1: t-BuOK / methanol / 1 h

2: 1.00 g / pyridine / 4 h

3: CSA / dimethylformamide / 1 h

4: 943 mg / aq. AcOH / 0.25 h

5: 53 percent / 1-benzenesulfinyl piperidine; tri-tert-butylpyrimidine; Tf₂O / 3 Angstroem molecular sieves / CH₂Cl₂ / -60 - 20 °C

6: 62 percent / CSA / tetrahydrofuran; methanol / 18 h

7: 72 percent / DMAP; pyridine / 6 h

8: 71 percent / 1-benzenesulfinyl piperidine; tri-tert-butylpyrimidine; Tf₂O / 3 Angstroem molecular sieves / CH₂Cl₂ / 2 h / -60 - -20 °C

9: ethylenediamine; 3 Angstroem molecular sieves / butan-1-ol / 12 h / 90 °C

10: 74 mg / pyridine / 3 h

11: Me₃P; H₂O / tetrahydrofuran / 72 h

12: 31 mg / pyridine / 16 h

With pyridine; dmap; 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,5-tri-tert-butylpyrimidine; 3 A molecular sieve; camphor-10-sulfonic acid; potassium tert-butylate; water; acetic acid; ethylenediamine; trimethylphosphane; 3 A molecular sieve; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; butan-1-ol;

DOI:10.1002/chem.200400862

Reference yield:

Acetic acid (2S,3R,4R,5S)-3,5-diacetoxy-2-acetoxymethyl-6-bromo-tetrahydro-pyran-4-yl ester (138514-71-3) → methyl 2-acetamido-4-O-acetyl-3-O-{2-acetamido-3-O-benzyl-4-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranosyl}-6-O-tert-butyldiphenylsilyl-2-deoxy-β-L-galactopyranoside (849222-10-2)

Guidance literature:

Multi-step reaction with 15 steps

1: 3.12 g / CuSO₄; Zn; aq. NaOAc / CH₂Cl₂ / 3 h / -10 °C

2: 61 percent / NaN₃; bisacetoxyiodobenzene / CH₂Cl₂ / 18 h

3: 91 percent / 1-benzenesulfinyl piperidine; tri-tert-butylpyrimidine; Tf₂O / 3 Angstroem molecular sieves / CH₂Cl₂ / -60 - 20 °C

4: t-BuOK / methanol / 1 h

5: 1.00 g / pyridine / 4 h

6: CSA / dimethylformamide / 1 h

7: 943 mg / aq. AcOH / 0.25 h

8: 53 percent / 1-benzenesulfinyl piperidine; tri-tert-butylpyrimidine; Tf₂O / 3 Angstroem molecular sieves / CH₂Cl₂ / -60 - 20 °C

9: 62 percent / CSA / tetrahydrofuran; methanol / 18 h

10: 72 percent / DMAP; pyridine / 6 h

11: 71 percent / 1-benzenesulfinyl piperidine; tri-tert-butylpyrimidine; Tf₂O / 3 Angstroem molecular sieves / CH₂Cl₂ / 2 h / -60 - -20 °C

12: ethylenediamine; 3 Angstroem molecular sieves / butan-1-ol / 12 h / 90 °C

13: 74 mg / pyridine / 3 h

14: Me₃P; H₂O / tetrahydrofuran / 72 h

15: 31 mg / pyridine / 16 h

With pyridine; dmap; sodium azide; 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; [bis(acetoxy)iodo]benzene; 2,4,5-tri-tert-butylpyrimidine; 3 A molecular sieve; camphor-10-sulfonic acid; potassium tert-butylate; water; sodium acetate; copper(II) sulfate; acetic acid; ethylenediamine; zinc; trimethylphosphane; 3 A molecular sieve; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; butan-1-ol;

DOI:10.1002/chem.200400862

upstream raw materials:

acetic anhydride

methyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-L-galactopyranoside

Acetic acid (2S,3R,4R,5S)-3,5-diacetoxy-2-acetoxymethyl-6-bromo-tetrahydro-pyran-4-yl ester

phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-seleno-α-L-galactopyranoside

Downstream raw materials:

methyl 2-acetamido-4-O-acetyl-3-O-{2-acetamido-3-O-benzyl-4-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-mannopyranosyl}-2-deoxy-β-L-galactopyranoside

C₄₈H₅₇N₃O₁₉