methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-α-D-altropyranoside

Base Information

• Chemical Name: methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-α-D-altropyranoside
• CAS No.: 280569-44-0
• Molecular Formula: C₂₉H₂₇NO₇
• Molecular Weight: 501.536
• Mol file: 280569-44-0.mol

Synonyms:methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-α-D-altropyranoside

Chemical Property of methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-α-D-altropyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-α-D-altropyranoside

There total 3 articles about methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-α-D-altropyranoside 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: 85.0%

phthalic monoacid monomethyl ester chloride (4397-55-1) + methyl 2-amino-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-altropyranoside (280569-43-9) → methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-α-D-altropyranoside (280569-44-0)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1080/07328300008544079

Reference yield:

Monomethyl phthalate (4376-18-5) → methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-α-D-altropyranoside (280569-44-0)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂

2: 85 percent / Et₃N / CH₂Cl₂ / 16 h / 20 °C

With thionyl chloride; triethylamine; In dichloromethane; 1: Chlorination / 2: cyclocondensation;

DOI:10.1080/07328300008544079

Reference yield:

(2R,4aR,6S,7S,8S,8aS)-7-Azido-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine → methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-α-D-altropyranoside (280569-44-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / LiAlH₄ / tetrahydrofuran / 1.5 h

2: 85 percent / Et₃N / CH₂Cl₂ / 16 h / 20 °C

With lithium aluminium tetrahydride; triethylamine; In tetrahydrofuran; dichloromethane; 1: Reduction / 2: cyclocondensation;

DOI:10.1080/07328300008544079

upstream raw materials:

phthalic monoacid monomethyl ester chloride

methyl 2-amino-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-altropyranoside

Monomethyl phthalate

Downstream raw materials:

methyl 3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-phthalimido-α-D-altropyranoside

methyl 3-O-benzyl-2-deoxy-2-phthalimido-α-D-altropyranoside