benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1-> 4)-2-O-benzoyl-6-O-benzyl-α-D-mannopyranoside 3,6'-malonate

Base Information

• Chemical Name: benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1-> 4)-2-O-benzoyl-6-O-benzyl-α-D-mannopyranoside 3,6'-malonate
• CAS No.: 220009-64-3
• Molecular Formula: C₅₇H₅₆O₁₄
• Molecular Weight: 965.063

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

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

Chemical Property:

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

There total 5 articles about benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1-> 4)-2-O-benzoyl-6-O-benzyl-α-D-mannopyranoside 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: 50.0%

benzyl 2-O-benzoyl-6-O-benzyl-3-O-[3-(ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranosid-6-O-yl)-1,3-dioxopropyl]-α-D-mannopyranoside (220009-48-3) → benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1-> 4)-2-O-benzoyl-6-O-benzyl-α-D-mannopyranoside 3,6'-malonate (220009-64-3) + benzyl O-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-(1-> 4)-2-O-benzoyl-6-O-benzyl-α-D-mannopyranoside 3,6'-malonate (220009-52-9)

Guidance literature:

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; In dichloromethane; at -30 ℃;

DOI:10.1002/1522-2675(20001004)83:10<2676::AID-HLCA2676>3.0.CO;2-K

Reference yield:

benzoyl chloride (98-88-4) → benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1-> 4)-2-O-benzoyl-6-O-benzyl-α-D-mannopyranoside 3,6'-malonate (220009-64-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 58 percent / Bu₄N(HSO₄); NaOH / H₂O; CH₂Cl₂ / 1.5 h / -5 °C

2: 63 percent / DCC; DMAP / CH₂Cl₂ / 24 h / 20 °C

3: 74 percent / NaCNBH₃; HCl; 3 Angstroem mol. sieves / diethyl ether; tetrahydrofuran

4: 36 percent / MeOTf; 4 Angstroem MS / acetonitrile / 6 h / 20 °C

With hydrogenchloride; dmap; sodium hydroxide; 3 A molecular sieve; 4 Angstroem MS; tetra(n-butyl)ammonium hydrogensulfate; sodium cyanoborohydride; dicyclohexyl-carbodiimide; methyl trifluoromethanesulfonate; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetonitrile; 1: Acylation / 2: Acylation / 3: reductive cleavage / 4: Cyclization;

DOI:10.1002/1522-2675(20001004)83:10<2676::AID-HLCA2676>3.0.CO;2-K

Reference yield:

benzyl 4,6-O-benzylidene-α-D-mannopyranoside (73366-72-0) → benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1-> 4)-2-O-benzoyl-6-O-benzyl-α-D-mannopyranoside 3,6'-malonate (220009-64-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 58 percent / Bu₄N(HSO₄); NaOH / H₂O; CH₂Cl₂ / 1.5 h / -5 °C

2: 63 percent / DCC; DMAP / CH₂Cl₂ / 24 h / 20 °C

3: 74 percent / NaCNBH₃; HCl; 3 Angstroem mol. sieves / diethyl ether; tetrahydrofuran

4: 36 percent / MeOTf; 4 Angstroem MS / acetonitrile / 6 h / 20 °C

With hydrogenchloride; dmap; sodium hydroxide; 3 A molecular sieve; 4 Angstroem MS; tetra(n-butyl)ammonium hydrogensulfate; sodium cyanoborohydride; dicyclohexyl-carbodiimide; methyl trifluoromethanesulfonate; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetonitrile; 1: Acylation / 2: Acylation / 3: reductive cleavage / 4: Cyclization;

DOI:10.1002/1522-2675(20001004)83:10<2676::AID-HLCA2676>3.0.CO;2-K

upstream raw materials:

benzyl 2-O-benzoyl-6-O-benzyl-3-O-[3-(ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranosid-6-O-yl)-1,3-dioxopropyl]-α-D-mannopyranoside

benzoyl chloride

benzyl 4,6-O-benzylidene-α-D-mannopyranoside

benzyl 2-O-benzoyl-4,6-O-benzylidene-α-D-mannopyranoside

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