1,5-Anhydro-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-D-ribo-hex-1-enitol

Base Information

• Chemical Name: 1,5-Anhydro-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-D-ribo-hex-1-enitol
• CAS No.: 144448-34-0
• Molecular Formula: C₅₆H₄₈N₂O₁₂
• Molecular Weight: 941.003
• Mol file: 144448-34-0.mol

Synonyms:

Chemical Property of 1,5-Anhydro-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-D-ribo-hex-1-enitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,5-Anhydro-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-D-ribo-hex-1-enitol

There total 4 articles about 1,5-Anhydro-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-D-ribo-hex-1-enitol 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: 27.0%

(+/-)-4S-<(benzyloxy)methyl>-3aS,6aR-dihydro-2-(dimethylamino)-5R,6R-dihydroxycyclopentano<4,3-d>oxazole (124583-64-8,124648-52-8,124648-53-9,124648-54-0,134875-86-8) + 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 → (3aR,4S,5S,6S,6aR)-6-<(Benzyloxy)methyl>-2-(dimethylamino)-3a,5,6,6a-tetrahydro-5-hydroxy-4H-cyclopentoxazol-4-yl 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-allopyranoside (144448-35-1) + 1,5-Anhydro-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-D-ribo-hex-1-enitol (144448-34-0) + (3aS,4S,5S,6R,6aR)-6-<(Benzyloxy)methyl>-2-(dimethylamino)-3a,5,6,6a-tetrahydro-4-hydroxy-4H-cyclopentoxazol-5-yl 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-allopyranoside (136773-87-0) + (3aR,4R,5R,6S,6aS)-6-<(Benzyloxy)methyl>-2-(dimethylamino)-3a,5,6,6a-tetrahydro-4-hydroxy-4H-cyclopentoxazol-5-yl 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-allopyranoside (136845-48-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at 0 ℃; for 0.333333h; Further byproducts given;

DOI:10.1002/hlca.19920750506

Reference yield:

(+/-)-4S-<(benzyloxy)methyl>-3aS,6aR-dihydro-2-(dimethylamino)-5R,6R-dihydroxycyclopentano<4,3-d>oxazole (124583-64-8,124648-52-8,124648-53-9,124648-54-0,134875-86-8) + 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 → (3aS,4R,5R,6R,6aS)-6-<(Benzyloxy)methyl>-2-(dimethylamino)-3a,5,6,6a-tetrahydro-5-hydroxy-4H-cyclopentoxazol-4-yl 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-allopyranoside (186041-04-3) + 1,5-Anhydro-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-D-ribo-hex-1-enitol (144448-34-0) + (3aS,4S,5S,6R,6aR)-6-<(Benzyloxy)methyl>-2-(dimethylamino)-3a,5,6,6a-tetrahydro-4-hydroxy-4H-cyclopentoxazol-5-yl 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-allopyranoside (136773-87-0) + (3aR,4R,5R,6S,6aS)-6-<(Benzyloxy)methyl>-2-(dimethylamino)-3a,5,6,6a-tetrahydro-4-hydroxy-4H-cyclopentoxazol-5-yl 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-allopyranoside (136845-48-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at 0 ℃; for 0.333333h; Yield given. Further byproducts given. Yields of byproduct given;

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) → 1,5-Anhydro-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-D-ribo-hex-1-enitol (144448-34-0)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 17 percent / trimethylsilyl triflate, 4-Angstroem molecular sieves / CH₂Cl₂ / 0.33 h / 0 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; potassium carbonate; In dichloromethane;

DOI:10.1002/hlca.19920750506

upstream raw materials:

(+/-)-4S-<(benzyloxy)methyl>-3aS,6aR-dihydro-2-(dimethylamino)-5R,6R-dihydroxycyclopentano<4,3-d>oxazole

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