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

Base Information

• Chemical Name: 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
• CAS No.: 188397-33-3
• Molecular Formula: C₆₄H₅₆F₅NO₂₁
• Molecular Weight: 1270.13

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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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-α-D-mannopyranosyl)-α-D-mannopyranosyl]-L-threonine pentafluorophenyl ester

There total 9 articles about 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 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-α-D-mannopyranosyl)-α-D-mannopyranosyl]-L-threonine pentafluorophenyl ester (188397-33-3)

Guidance literature:

Multi-step reaction with 8 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

6: HOBt, H₂O / acetonitrile; dimethylformamide / Ambient temperature

7: diisopropylethylammonium hydrazine, 4-ethylmorpholine, H₂O / acetonitrile; dimethylformamide / 1.5 h / Ambient temperature

8: 1.) dicyclohexylcarbodiimide, 3 Angstroem sieves / 1.) CH₂Cl₂, 0 deg C, 30 min, 2.) CH₂Cl₂, 0 deg C, 5 h

With N-ethylmorpholine;; pyridine; 2,6-di-tert-butyl-4-methylpyridine; 3 A molecular sieve; 4 A molecular sieve; diisopropylethylammonium hydrazine; water; hydrogen bromide; bromine; silver trifluoromethanesulfonate; benzotriazol-1-ol; acetic acid; dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

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-α-D-mannopyranosyl)-α-D-mannopyranosyl]-L-threonine pentafluorophenyl ester (188397-33-3)

Guidance literature:

Multi-step reaction with 9 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

7: HOBt, H₂O / acetonitrile; dimethylformamide / Ambient temperature

8: diisopropylethylammonium hydrazine, 4-ethylmorpholine, H₂O / acetonitrile; dimethylformamide / 1.5 h / Ambient temperature

9: 1.) dicyclohexylcarbodiimide, 3 Angstroem sieves / 1.) CH₂Cl₂, 0 deg C, 30 min, 2.) CH₂Cl₂, 0 deg C, 5 h

With N-ethylmorpholine;; pyridine; 2,6-di-tert-butyl-4-methylpyridine; 3 A molecular sieve; 4 A molecular sieve; diisopropylethylammonium hydrazine; water; hydrogen bromide; bromine; silver trifluoromethanesulfonate; benzotriazol-1-ol; toluene-4-sulfonic acid; acetic acid; dicyclohexyl-carbodiimide; In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

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

Reference yield:

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) → Nα-(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 (188397-33-3)

Guidance literature:

Multi-step reaction with 3 steps

1: HOBt, H₂O / acetonitrile; dimethylformamide / Ambient temperature

2: diisopropylethylammonium hydrazine, 4-ethylmorpholine, H₂O / acetonitrile; dimethylformamide / 1.5 h / Ambient temperature

3: 1.) dicyclohexylcarbodiimide, 3 Angstroem sieves / 1.) CH₂Cl₂, 0 deg C, 30 min, 2.) CH₂Cl₂, 0 deg C, 5 h

With N-ethylmorpholine;; 3 A molecular sieve; diisopropylethylammonium hydrazine; water; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; acetonitrile;

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

upstream raw materials:

2,3,4,5,6-pentafluorophenol

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

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-6-O-phosphate-α-D-mannopyranosyl)-α-D-mannopyranosyl]-L-threonine pentafluorophenyl ester

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