N^α-(fluoren-9-ylmethoxycarbonyl)-O-[3,4,6-tri-O-acetyl-2-O-(2,3,4-tri-O-benzoyl-6-O-chloroacetyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-L-threonine pentafluorophenyl ester

Base Information

• Chemical Name: N^α-(fluoren-9-ylmethoxycarbonyl)-O-[3,4,6-tri-O-acetyl-2-O-(2,3,4-tri-O-benzoyl-6-O-chloroacetyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-L-threonine pentafluorophenyl ester
• CAS No.: 188397-31-1
• Molecular Formula: C₆₆H₅₇ClF₅NO₂₂
• Molecular Weight: 1346.62

Synonyms:

Chemical Property of N^α-(fluoren-9-ylmethoxycarbonyl)-O-[3,4,6-tri-O-acetyl-2-O-(2,3,4-tri-O-benzoyl-6-O-chloroacetyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-L-threonine pentafluorophenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N^α-(fluoren-9-ylmethoxycarbonyl)-O-[3,4,6-tri-O-acetyl-2-O-(2,3,4-tri-O-benzoyl-6-O-chloroacetyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-L-threonine pentafluorophenyl ester

There total 6 articles about N^α-(fluoren-9-ylmethoxycarbonyl)-O-[3,4,6-tri-O-acetyl-2-O-(2,3,4-tri-O-benzoyl-6-O-chloroacetyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-L-threonine pentafluorophenyl ester 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:

phenyl 2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside (150935-65-2) → Nα-(fluoren-9-ylmethoxycarbonyl)-O-[3,4,6-tri-O-acetyl-2-O-(2,3,4-tri-O-benzoyl-6-O-chloroacetyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-L-threonine pentafluorophenyl ester (188397-31-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / pyridine / CH₂Cl₂ / 1.5 h / Ambient temperature

2: 100 percent / Br₂, 4 Angstroem sieves / CH₂Cl₂ / 4.5 h

3: 1.) silver triflate, 3 Angstroem sieves, 2.) 2,6-di-tert-butyl-4-methylpyridine / 1.) CH₂Cl₂, -30 deg C, 7 h, 2.) CH₂Cl₂, -30 deg C, overnight

4: 91 percent / HBr, AcOH, 3 Angstroem sieves / CH₂Cl₂ / 1.5 h / Ambient temperature

5: 1.) silver triflate, 3 Angstroem sieves, 2.) 2,6-di-tert-butyl-4-methylpyridine / 1.) CH₂Cl₂, -20 deg C, 3 h, 2.) CH₂Cl₂, 30 min

With pyridine; 2,6-di-tert-butyl-4-methylpyridine; 3 A molecular sieve; 4 A molecular sieve; hydrogen bromide; bromine; silver trifluoromethanesulfonate; acetic acid; In dichloromethane;

DOI:10.1016/S0968-0896(96)00194-0

Reference yield:

phenyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside (150935-64-1) → Nα-(fluoren-9-ylmethoxycarbonyl)-O-[3,4,6-tri-O-acetyl-2-O-(2,3,4-tri-O-benzoyl-6-O-chloroacetyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-L-threonine pentafluorophenyl ester (188397-31-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 94 percent / TsOH*H₂O / acetonitrile; H₂O / 5.5 h / Ambient temperature

2: 90 percent / pyridine / CH₂Cl₂ / 1.5 h / Ambient temperature

3: 100 percent / Br₂, 4 Angstroem sieves / CH₂Cl₂ / 4.5 h

4: 1.) silver triflate, 3 Angstroem sieves, 2.) 2,6-di-tert-butyl-4-methylpyridine / 1.) CH₂Cl₂, -30 deg C, 7 h, 2.) CH₂Cl₂, -30 deg C, overnight

5: 91 percent / HBr, AcOH, 3 Angstroem sieves / CH₂Cl₂ / 1.5 h / Ambient temperature

6: 1.) silver triflate, 3 Angstroem sieves, 2.) 2,6-di-tert-butyl-4-methylpyridine / 1.) CH₂Cl₂, -20 deg C, 3 h, 2.) CH₂Cl₂, 30 min

With pyridine; 2,6-di-tert-butyl-4-methylpyridine; 3 A molecular sieve; 4 A molecular sieve; hydrogen bromide; bromine; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; acetic acid; In dichloromethane; water; acetonitrile;

DOI:10.1016/S0968-0896(96)00194-0

Reference yield:

2,3,4-tri-O-benzoyl-6-O-chloroacetyl-α-D-mannopyranosyl bromide (188397-28-6) → Nα-(fluoren-9-ylmethoxycarbonyl)-O-[3,4,6-tri-O-acetyl-2-O-(2,3,4-tri-O-benzoyl-6-O-chloroacetyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-L-threonine pentafluorophenyl ester (188397-31-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) silver triflate, 3 Angstroem sieves, 2.) 2,6-di-tert-butyl-4-methylpyridine / 1.) CH₂Cl₂, -30 deg C, 7 h, 2.) CH₂Cl₂, -30 deg C, overnight

2: 91 percent / HBr, AcOH, 3 Angstroem sieves / CH₂Cl₂ / 1.5 h / Ambient temperature

3: 1.) silver triflate, 3 Angstroem sieves, 2.) 2,6-di-tert-butyl-4-methylpyridine / 1.) CH₂Cl₂, -20 deg C, 3 h, 2.) CH₂Cl₂, 30 min

With 2,6-di-tert-butyl-4-methylpyridine; 3 A molecular sieve; hydrogen bromide; silver trifluoromethanesulfonate; acetic acid; In dichloromethane;

DOI:10.1016/S0968-0896(96)00194-0

upstream raw materials:

N^α-(9-fluorenylmethoxycarbonyl)-L-threonine pentafluorophenyl ester

C₄₁H₄₀BrClO₁₇

phenyl 2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside

phenyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside

Downstream raw materials:

N^α-(fluoren-9-ylmethoxycarbonyl)-O-[3,4,6-tri-O-acetyl-2-O-(2,3,4-tri-O-benzoyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-L-threonine pentafluorophenyl ester

N^α-(fluoren-9-ylmethoxycarbonyl)-O-[3,4,6-tri-O-acetyl-2-O-(2,3,4-tri-O-benzoyl-6-O-phosphate-α-D-mannopyranosyl)-α-D-mannopyranosyl]-L-threonine pentafluorophenyl ester

N^α-(fluoren-9-ylmethoxycarbonyl)-O-[3,4,6-tri-O-acetyl-2-O-(2,3,4-tri-O-benzoyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-L-threonine

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