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

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
• CAS No.: 188397-32-2
• Molecular Formula: C₅₈H₅₇NO₂₁
• Molecular Weight: 1104.08

Synonyms:

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

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-α-D-mannopyranosyl)-α-D-mannopyranosyl]-L-threonine

There total 8 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 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:

C60H58ClNO22 → 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 (188397-32-2)

Guidance literature:

With N-ethylmorpholine;; diisopropylethylammonium hydrazine; water; In N,N-dimethyl-formamide; acetonitrile; for 1.5h; Yield given; Ambient temperature;

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 (188397-32-2)

Guidance literature:

Multi-step reaction with 8 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

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; In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

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

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 (188397-32-2)

Guidance literature:

Multi-step reaction with 7 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

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; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

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

upstream raw materials:

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

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

2,3,4-tri-O-benzoyl-6-O-chloroacetyl-α-D-mannopyranosyl bromide

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

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

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