p-Methoxyphenylmethyl 4,6-di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-<2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylmethyl(xanthateimidazole)>-α-D-mannopyranoside

Base Information

• Chemical Name: p-Methoxyphenylmethyl 4,6-di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-<2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylmethyl(xanthateimidazole)>-α-D-mannopyranoside
• CAS No.: 220931-26-0
• Molecular Formula: C₇₃H₈₀N₂O₁₄SSi
• Molecular Weight: 1269.59
• Mol file: 220931-26-0.mol

Synonyms:p-Methoxyphenylmethyl 4,6-di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-<2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylmethyl(xanthateimidazole)>-α-D-mannopyranoside

Chemical Property of p-Methoxyphenylmethyl 4,6-di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-<2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylmethyl(xanthateimidazole)>-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-Methoxyphenylmethyl 4,6-di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-<2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylmethyl(xanthateimidazole)>-α-D-mannopyranoside

There total 10 articles about p-Methoxyphenylmethyl 4,6-di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-<2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylmethyl(xanthateimidazole)>-α-D-mannopyranoside 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: 99.0%

1,1'-Thiocarbonyldiimidazole (6160-65-2) + p-Methoxyphenylmethyl 4,6-di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-(2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylhydroxy-methyl)-α-D-mannopyranoside (188893-20-1) → p-Methoxyphenylmethyl 4,6-di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-<2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylmethyl(xanthateimidazole)>-α-D-mannopyranoside (220931-26-0)

Guidance literature:

In acetonitrile; Heating;

DOI:10.1002/(SICI)1521-3765(19990201)5:2<430::AID-CHEM430>3.0.CO;2-D

Reference yield:

(2R,3S,4R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol (87316-22-1) → p-Methoxyphenylmethyl 4,6-di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-<2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylmethyl(xanthateimidazole)>-α-D-mannopyranoside (220931-26-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) Bu₂SnO, 2.) nBu₄NBr / 1.) toluene, reflux, 4 h, 2.) toluene, 20 deg C, 15 h

2: 94 percent / nBuN₄F / tetrahydrofuran / 0.25 h / 20 °C

3: 99 percent / pyridine / 12 h / 0 °C

4: 74 percent / 3 Angstroem molecular sieves, N-iodosuccinimide / acetonitrile / 1.) 20 deg C, 10 min, 2.) 20 deg C, overnight

5: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂

6: Bu₃SnH, AIBN / benzene / 4 h / Heating

7: 85 percent / SmI₂ / tetrahydrofuran / 0.17 h / 20 °C

8: 99 percent / acetonitrile / Heating

With pyridine; N-iodo-succinimide; samarium diiodide; 2,2'-azobis(isobutyronitrile); 3 A molecular sieve; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; tri-n-butyl-tin hydride; di(n-butyl)tin oxide; ozone; triphenylphosphine; In tetrahydrofuran; acetonitrile; benzene;

DOI:10.1002/(SICI)1521-3765(19990201)5:2<430::AID-CHEM430>3.0.CO;2-D

Reference yield:

benzoyl chloride (98-88-4) → p-Methoxyphenylmethyl 4,6-di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-<2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylmethyl(xanthateimidazole)>-α-D-mannopyranoside (220931-26-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 99 percent / pyridine / 12 h / 0 °C

2: 74 percent / 3 Angstroem molecular sieves, N-iodosuccinimide / acetonitrile / 1.) 20 deg C, 10 min, 2.) 20 deg C, overnight

3: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂

4: Bu₃SnH, AIBN / benzene / 4 h / Heating

5: 85 percent / SmI₂ / tetrahydrofuran / 0.17 h / 20 °C

6: 99 percent / acetonitrile / Heating

With pyridine; N-iodo-succinimide; samarium diiodide; 2,2'-azobis(isobutyronitrile); 3 A molecular sieve; tri-n-butyl-tin hydride; ozone; triphenylphosphine; In tetrahydrofuran; acetonitrile; benzene;

DOI:10.1002/(SICI)1521-3765(19990201)5:2<430::AID-CHEM430>3.0.CO;2-D

upstream raw materials:

1,1'-Thiocarbonyldiimidazole

p-Methoxyphenylmethyl 4,6-di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-(2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylhydroxy-methyl)-α-D-mannopyranoside

(2R,3S,4R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol

benzoyl chloride

Downstream raw materials:

4,6-Di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-(2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylmethyl)-D-mannopyranosyl 2-pyridylsulfone

4,6-Di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-(2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylmethyl)-D-mannopyranosyl 2-pyridylsulfide

4,6-Di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-(2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylmethyl)-α-D-mannopyranoside

p-Methoxyphenylmethyl 4,6-di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-(2-O-tert-butyldimethylsilyl-3,4,6-tri-O-benzyl-α-D-mannopyranosylmethyl)-α-D-mannopyranoside