p-nitrophenyl 2,3-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-mannopyranoside

Base Information

• Chemical Name: p-nitrophenyl 2,3-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-mannopyranoside
• CAS No.: 213385-98-9
• Molecular Formula: C₂₂H₂₅NO₁₀S
• Molecular Weight: 495.507
• Mol file: 213385-98-9.mol

Synonyms:p-nitrophenyl 2,3-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-mannopyranoside

Chemical Property of p-nitrophenyl 2,3-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-nitrophenyl 2,3-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-mannopyranoside

There total 1 articles about p-nitrophenyl 2,3-O-isopropylidene-6-O-p-toluenesulfonyl-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: 70.0%

p-nitrophenyl 2,3-O-isopropylidene-α-D-mannopyranoside (80264-82-0) + p-toluenesulfonyl chloride (98-59-9) → p-nitrophenyl 2,3-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-mannopyranoside (213385-98-9)

Guidance literature:

In pyridine; at 60 ℃; for 1.5h;

DOI:10.1016/S0008-6215(98)00074-3

Reference yield: 73.0%

p-nitrophenyl 2,3-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-mannopyranoside (213385-98-9) → p-nitrophenyl 6-deoxy-6-iodo-2,3-O-isopropylidene-α-D-mannopyranoside (213385-99-0)

Guidance literature:

With sodium iodide; In N,N-dimethyl-formamide; at 100 ℃; for 5h;

DOI:10.1016/S0008-6215(98)00074-3

Reference yield:

p-nitrophenyl 2,3-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-mannopyranoside (213385-98-9) → 2,2,2-Trifluoro-N-{4-[(2R,3S,4S,5R,6R)-4-((2S,3R,4R,5S,6S)-5-formylamino-4-hydroxy-3-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-5-hydroxy-3-methoxy-6-methyl-tetrahydro-pyran-2-yloxy]-phenyl}-acetamide

Guidance literature:

Multi-step reaction with 8 steps

1: 73 percent / NaI / dimethylformamide / 5 h / 100 °C

2: 53 percent / LiAlH₄ / tetrahydrofuran / 20 h / Ambient temperature

3: 75 percent / KOH / dimethylformamide / 0.67 h / 0 °C

4: 90 percent / CF₃CO₂H, H₂O / CH₂Cl₂ / 0.17 h / Ambient temperature

5: 90 percent / Bu₄NBr / CH₂Cl₂; aq. NaOH

6: 35 percent / TMSOTf, 4 Angstroem molecular sieves / CH₂Cl₂ / 0.25 h / -30 °C

7: 1.) H₂; 2.) pyridine / 1.) PtO₂ / 1.) EtOAc, r.t., 2 h; 2.) EtOAc, r.t., 1 h

8: H₂ / Pd(OH)2 / methanol

With pyridine; potassium hydroxide; lithium aluminium tetrahydride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutylammomium bromide; water; hydrogen; trifluoroacetic acid; sodium iodide; platinum(IV) oxide; palladium dihydroxide; In tetrahydrofuran; methanol; sodium hydroxide; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(98)00074-3

upstream raw materials:

p-nitrophenyl 2,3-O-isopropylidene-α-D-mannopyranoside

p-toluenesulfonyl chloride

Downstream raw materials:

p-nitrophenyl 6-deoxy-6-iodo-2,3-O-isopropylidene-α-D-mannopyranoside

p-nitrophenyl 6-deoxy-2,3-O-isopropylidene-α-D-mannopyranoside

p-nitrophenyl 4-O-benzyl-6-deoxy-α-D-mannopyranoside

p-nitrophenyl 4-O-benzyl-6-deoxy-2-O-methyl-α-D-mannopyranoside