benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1-> 4)-6-O-benzyl-2-deoxy-2-phthalimido-α-D-glucopyranoside 3,6'-malonate

Base Information

Chemical Name:benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1-> 4)-6-O-benzyl-2-deoxy-2-phthalimido-α-D-glucopyranoside 3,6'-malonate
CAS No.:220009-66-5
Molecular Formula:C₅₈H₅₅NO₁₄
Molecular Weight:990.073
Hs Code.:

Synonyms:benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1-> 4)-6-O-benzyl-2-deoxy-2-phthalimido-α-D-glucopyranoside 3,6'-malonate

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Chemical Property of benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1-> 4)-6-O-benzyl-2-deoxy-2-phthalimido-α-D-glucopyranoside 3,6'-malonate

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Technology Process of benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1-> 4)-6-O-benzyl-2-deoxy-2-phthalimido-α-D-glucopyranoside 3,6'-malonate

There total 7 articles about benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1-> 4)-6-O-benzyl-2-deoxy-2-phthalimido-α-D-glucopyranoside 3,6'-malonate 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: 52.0%

: 220009-59-6
benzyl 6-O-benzyl-2-deoxy-3-O-[3-(ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranosid-6-O-yl)-1,3-dioxopropyl]-2-phthalimido-α-D-glucopyranoside

: 220009-66-5
benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1-> 4)-6-O-benzyl-2-deoxy-2-phthalimido-α-D-glucopyranoside 3,6'-malonate

Guidance literature:: With methyl trifluoromethanesulfonate; In acetonitrile; at 20 ℃; for 6h;
DOI:10.1016/S0040-4020(99)01053-4

Reference yield:

: 260779-97-3
ethyl 2,3,4-tri-O-benzyl-6-O-(hydroxycarbonylethanoyl)-1-thio-α-D-mannopyranoside

: 220009-66-5
benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1-> 4)-6-O-benzyl-2-deoxy-2-phthalimido-α-D-glucopyranoside 3,6'-malonate

Guidance literature:: Multi-step reaction with 3 steps

1: 80 percent / Bu₃N; 2-chloro-1-methylpyridinium iodide / CH₂Cl₂ / 2.5 h / 20 °C

2: 65 percent / Et₃SiH; CF₃COOH / CH₂Cl₂ / 2.5 h / 20 °C

3: 52 percent / MeOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

With triethylsilane; tributyl-amine; 4 A molecular sieve; 2-chloro-1-methyl-pyridinium iodide; trifluoroacetic acid; methyl trifluoromethanesulfonate; In dichloromethane; 1: Acylation / 2: Ring cleavage / 3: Cyclization;
DOI:10.1002/1522-2675(20001004)83:10<2676::AID-HLCA2676>3.0.CO;2-K

Reference yield:

: 39483-51-7,119645-03-3,126461-54-9,128850-50-0
ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranoside

: 220009-66-5
benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1-> 4)-6-O-benzyl-2-deoxy-2-phthalimido-α-D-glucopyranoside 3,6'-malonate

Guidance literature:: Multi-step reaction with 5 steps

1: 64 percent / 1-hydroxy-1H-benzotriazole; DCC / CH₂Cl₂ / 24 h / 20 °C

2: 100 percent / TFA / 3 h / 20 °C

3: 80 percent / n-Bu₃N; 2-chloro-1-methyl-pyrimidiniumiodide / CH₂Cl₂ / 2.5 h

4: 65 percent / Et₃SiH; CF₃CO₂H / tetrahydrofuran / 2.5 h / 20 °C

5: 52 percent / MeOTf / acetonitrile / 6 h / 20 °C

With triethylsilane; tributyl-amine; 2-chloro-1-methylpyrimidinium iodide; benzotriazol-1-ol; dicyclohexyl-carbodiimide; trifluoroacetic acid; methyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; acetonitrile; 1: Esterification / 2: Hydrolysis / 3: Acylation / 4: Ring cleavage / 5: Cyclization;
DOI:10.1016/S0040-4020(99)01053-4