4-chlorophenyl 2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

Base Information

Chemical Name:4-chlorophenyl 2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside
CAS No.:296769-11-4
Molecular Formula:C₅₃H₅₂ClNO₁₄S
Molecular Weight:994.513
Hs Code.:

Synonyms:4-chlorophenyl 2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

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Chemical Property of 4-chlorophenyl 2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

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Technology Process of 4-chlorophenyl 2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

There total 4 articles about 4-chlorophenyl 2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 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%

: 296769-15-8
4-chlorophenyl 3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

: 7772-87-4
3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl chloride

: 296769-11-4
4-chlorophenyl 2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

Guidance literature:: With silver trifluoromethanesulfonate; silver carbonate;
DOI:10.1021/ol0063050

Reference yield:

: 10022-13-6
1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

: 296769-11-4
4-chlorophenyl 2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 73 percent / BF₃*Et₂O / CH₂Cl₂

2: 92 percent / Ph₂SCl⁽¹⁺⁾*Cl^(1-) / CH₂Cl₂ / 1.5 h / -78 - 20 °C

3: 62 percent / Ag₂CO₃; AgOTf

With boron trifluoride diethyl etherate; silver trifluoromethanesulfonate; silver carbonate; diphenylchlorosulfonium chloride; In dichloromethane; 1: Substitution / 2: Substitution / 3: glycosidation;
DOI:10.1021/ol0063050

Reference yield:

: 4-chlorophenyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

: 296769-11-4
4-chlorophenyl 2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: NaOMe / methanol

2: 62 percent / Ag₂CO₃; AgOTf

With sodium methylate; silver trifluoromethanesulfonate; silver carbonate; In methanol; 1: Deacetylation / 2: glycosidation;
DOI:10.1021/ol0063050