3,6-Di-O-benzyl-4-O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-β-D-allopyranose

Base Information

• Chemical Name: 3,6-Di-O-benzyl-4-O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-β-D-allopyranose
• CAS No.: 136773-85-8
• Molecular Formula: C₅₆H₅₀N₂O₁₃
• Molecular Weight: 959.019
• Mol file: 136773-85-8.mol

Synonyms:3,6-Di-O-benzyl-4-O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-β-D-allopyranose

Chemical Property of 3,6-Di-O-benzyl-4-O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-β-D-allopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,6-Di-O-benzyl-4-O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-β-D-allopyranose

There total 1 articles about 3,6-Di-O-benzyl-4-O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-β-D-allopyranose 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:

C59H54N2O13 → 3,6-Di-O-benzyl-4-O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-β-D-allopyranose (136773-85-8)

Guidance literature:

With water; mercury dichloride; mercury(II) oxide; In acetone; for 1h; Yield given; Ambient temperature;

DOI:10.1002/hlca.19920750506

Reference yield: 90.0%

3,6-Di-O-benzyl-4-O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-β-D-allopyranose (136773-85-8) + trichloroacetonitrile (545-06-2) → 3,6-Di-O-benzyl-4-O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-β-D-allopyranosyl trichloroacetimidate

Guidance literature:

With potassium carbonate; In dichloromethane; for 16h; Ambient temperature;

DOI:10.1002/hlca.19920750506

Reference yield:

3,6-Di-O-benzyl-4-O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-β-D-allopyranose (136773-85-8) → allosamidin (144539-85-5,103782-08-7,153322-50-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / K₂CO₃ / CH₂Cl₂ / 16 h / Ambient temperature

2: 27 percent / trimethylsilyl triflate, 4-Angstroem molecular sieves / CH₂Cl₂ / 0.33 h / 0 °C

3: 40 percent aq. MeNH₂ / ethanol / 48 h / Ambient temperature

4: pyridine / 14 h / Ambient temperature

5: 96 percent / 1 mM methanolic NaOMe / methanol / 10 h / Ambient temperature

6: 95 percent / hydrogen / 10 percent Pd/C / methanol; acetic acid / 36 h / 5250.4 Torr / Ambient temperature

With pyridine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; hydrogen; sodium methylate; potassium carbonate; methylamine; palladium on activated charcoal; In methanol; ethanol; dichloromethane; acetic acid;

DOI:10.1002/hlca.19920750506

Downstream raw materials:

allosamidin

Isoallosamidin

(3aS,4S,5S,6R,6aR)-6-<(Benzyloxy)methyl>-2-(dimethylamino)-3a,5,6,6a-tetrahydro-4-hydroxy-4H-cyclopentoxazol-5-yl 2-acetamido-4-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-allopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-allopyranoside

(3aR,4R,5R,6S,6aS)-6-<(Benzyloxy)methyl>-2-(dimethylamino)-3a,5,6,6a-tetrahydro-4-hydroxy-4H-cyclopentoxazol-5-yl 2-acetamido-4-O-(2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-allopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-allopyranoside