Allyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-allopyranoside

Base Information

• Chemical Name: Allyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-allopyranoside
• CAS No.: 144221-82-9
• Molecular Formula: C₂₆H₂₇NO₈
• Molecular Weight: 481.502
• Mol file: 144221-82-9.mol

Synonyms:Allyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-allopyranoside

Chemical Property of Allyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-allopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Allyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-allopyranoside

There total 5 articles about Allyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-allopyranoside 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:

phthalic anhydride (85-44-9) → Allyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-allopyranoside (144221-82-9)

Guidance literature:

Multi-step reaction with 3 steps

1: NEt₃ / methanol / 0.5 h / Ambient temperature

2: pyridine / 16 h / Ambient temperature

3: 1.) NaBH₃CN, 4-Angstroem molecular sieves, 2.) satd. HCl/Et₂O / 1.) THF, 0 deg C, 2 h

With pyridine; hydrogenchloride; diethyl ether; 4 A molecular sieve; sodium cyanoborohydride; triethylamine; In methanol;

DOI:10.1002/hlca.19920750505

Reference yield:

Allyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside (138456-61-8) → Allyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-allopyranoside (144221-82-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1 N aq. NaOH / 144 h / Heating

2: NEt₃ / methanol / 0.5 h / Ambient temperature

3: pyridine / 16 h / Ambient temperature

4: 1.) NaBH₃CN, 4-Angstroem molecular sieves, 2.) satd. HCl/Et₂O / 1.) THF, 0 deg C, 2 h

With pyridine; hydrogenchloride; sodium hydroxide; diethyl ether; 4 A molecular sieve; sodium cyanoborohydride; triethylamine; In methanol;

DOI:10.1002/hlca.19920750505

Reference yield:

(2R,4aR,6R,7R,8S,8aS)-6-Allyloxy-7-amino-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol (133227-65-3,136773-79-0) → Allyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-allopyranoside (144221-82-9)

Guidance literature:

Multi-step reaction with 3 steps

1: NEt₃ / methanol / 0.5 h / Ambient temperature

2: pyridine / 16 h / Ambient temperature

3: 1.) NaBH₃CN, 4-Angstroem molecular sieves, 2.) satd. HCl/Et₂O / 1.) THF, 0 deg C, 2 h

With pyridine; hydrogenchloride; diethyl ether; 4 A molecular sieve; sodium cyanoborohydride; triethylamine; In methanol;

DOI:10.1002/hlca.19920750505

upstream raw materials:

Allyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-allopyranoside

phthalic anhydride

Allyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside

(2R,4aR,6R,7R,8S,8aS)-6-Allyloxy-7-amino-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Downstream raw materials:

3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-2-phthalimido-D-arabino-hex-1-enitol

Allyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-allopyranosyl)-β-D-allopyranoside