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

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-mannopyranosylhydroxy-methyl)-α-D-mannopyranoside
CAS No.:188893-20-1
Molecular Formula:C₆₉H₇₈O₁₄Si
Molecular Weight:1159.46
Hs Code.:

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

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-mannopyranosylhydroxy-methyl)-α-D-mannopyranoside

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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-mannopyranosylhydroxy-methyl)-α-D-mannopyranoside

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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-mannopyranosylhydroxy-methyl)-α-D-mannopyranoside

There total 9 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-mannopyranosylhydroxy-methyl)-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: 85.0%

: 181506-87-6
2-[(2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-sulfonyl]-pyridine

: 188893-05-2
p-Methoxyphenylmethyl 4,6-di-O-benzoyl-3-O-benzyl-2-deoxy-2-C-formyl-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-mannopyranosylhydroxy-methyl)-α-D-mannopyranoside

Guidance literature:: With samarium diiodide; In tetrahydrofuran; at 20 ℃;
DOI:10.1016/S0040-4039(97)00206-2

Reference yield:

: 87316-22-1
(2R,3S,4R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol

: 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-mannopyranosylhydroxy-methyl)-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 7 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

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:

: 98-88-4
benzoyl chloride

: 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-mannopyranosylhydroxy-methyl)-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 5 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

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