methyl 4-O-acetyl-2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-β-L-galactopyranoside

Base Information

• Chemical Name: methyl 4-O-acetyl-2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-β-L-galactopyranoside
• CAS No.: 849222-03-3
• Molecular Formula: C₂₅H₃₃N₃O₆Si
• Molecular Weight: 499.639

Synonyms:methyl 4-O-acetyl-2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-β-L-galactopyranoside

Chemical Property of methyl 4-O-acetyl-2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-β-L-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of methyl 4-O-acetyl-2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-β-L-galactopyranoside

There total 8 articles about methyl 4-O-acetyl-2-azido-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:

Acetic acid (2S,3R,4R,5S)-3,5-diacetoxy-2-acetoxymethyl-6-bromo-tetrahydro-pyran-4-yl ester (138514-71-3) → methyl 4-O-acetyl-2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-β-L-galactopyranoside (849222-03-3)

Guidance literature:

Multi-step reaction with 7 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

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

DOI:10.1002/chem.200400862

Reference yield:

phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-seleno-α-L-galactopyranoside (849222-00-0) → methyl 4-O-acetyl-2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-β-L-galactopyranoside (849222-03-3)

Guidance literature:

Multi-step reaction with 5 steps

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

2: t-BuOK / methanol / 1 h

3: 1.00 g / pyridine / 4 h

4: CSA / dimethylformamide / 1 h

5: 943 mg / aq. AcOH / 0.25 h

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

DOI:10.1002/chem.200400862

Reference yield:

3,4,6-tri-O-acetyl-L-galactal (849221-99-4) → methyl 4-O-acetyl-2-azido-6-O-tert-butyldiphenylsilyl-2-deoxy-β-L-galactopyranoside (849222-03-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 61 percent / NaN₃; bisacetoxyiodobenzene / CH₂Cl₂ / 18 h

2: 91 percent / 1-benzenesulfinyl piperidine; tri-tert-butylpyrimidine; Tf₂O / 3 Angstroem molecular sieves / CH₂Cl₂ / -60 - 20 °C

3: t-BuOK / methanol / 1 h

4: 1.00 g / pyridine / 4 h

5: CSA / dimethylformamide / 1 h

6: 943 mg / aq. AcOH / 0.25 h

With pyridine; sodium azide; 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; [bis(acetoxy)iodo]benzene; 2,4,5-tri-tert-butylpyrimidine; camphor-10-sulfonic acid; potassium tert-butylate; acetic acid; 3 A molecular sieve; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/chem.200400862

upstream raw materials:

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

(2S,3S,4S,5S,6S)-5-Azido-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-3,4-diol

Downstream raw materials:

methyl 4-O-acetyl-2-azido-3-O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-mannopyranosyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-β-L-galactopyranoside

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

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

methyl 4-O-acetyl-2-azido-3-O-{2-azido-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

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