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

Base Information

• Chemical Name: methyl 3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-tetrachlorophthalimido-α-D-altropyranoside
• CAS No.: 280569-53-1
• Molecular Formula: C₂₄H₂₀Cl₅NO₈
• Molecular Weight: 627.69

Synonyms:methyl 3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-tetrachlorophthalimido-α-D-altropyranoside

Chemical Property of methyl 3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-tetrachlorophthalimido-α-D-altropyranoside

Chemical Property:

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Technology Process of methyl 3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-tetrachlorophthalimido-α-D-altropyranoside

There total 5 articles about methyl 3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-tetrachlorophthalimido-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: 62.0%

chloroacetyl chloride (79-04-9) + methyl 3-O-benzyl-2-deoxy-2-tetrachlorophthalimido-α-D-altropyranoside (280569-49-5) → methyl 3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-tetrachlorophthalimido-α-D-altropyranoside (280569-53-1)

Guidance literature:

With pyridine; at -50 ℃; for 1h;

DOI:10.1080/07328300008544079

Reference yield:

tetrachlorophthalic anhydride (117-08-8) → methyl 3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-tetrachlorophthalimido-α-D-altropyranoside (280569-53-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 54 percent / DIPEA / CH₂Cl₂ / 4 h / Heating

2: 77 percent / aq. TFA / CH₂Cl₂ / 0.5 h / 20 °C

3: 62 percent / pyridine / 1 h / -50 °C

With pyridine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane; 1: Condensation / 2: Hydrolysis / 3: Acylation;

DOI:10.1080/07328300008544079

Reference yield:

methyl 2-amino-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-altropyranoside (280569-43-9) → methyl 3-O-benzyl-6-O-chloroacetyl-2-deoxy-2-tetrachlorophthalimido-α-D-altropyranoside (280569-53-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 54 percent / DIPEA / CH₂Cl₂ / 4 h / Heating

2: 77 percent / aq. TFA / CH₂Cl₂ / 0.5 h / 20 °C

3: 62 percent / pyridine / 1 h / -50 °C

With pyridine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane; 1: Condensation / 2: Hydrolysis / 3: Acylation;

DOI:10.1080/07328300008544079

upstream raw materials:

chloroacetyl chloride

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

tetrachlorophthalic anhydride

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

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