benzyl O-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)(1->4)-2-O-benzoyl-6-O-benzyl-α-D-glucopyranoside-3,6-phthalate

Base Information

• Chemical Name: benzyl O-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)(1->4)-2-O-benzoyl-6-O-benzyl-α-D-glucopyranoside-3,6-phthalate
• CAS No.: 262605-65-2
• Molecular Formula: C₆₂H₅₈O₁₄
• Molecular Weight: 1027.13

Synonyms:benzyl O-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)(1->4)-2-O-benzoyl-6-O-benzyl-α-D-glucopyranoside-3,6-phthalate

Chemical Property of benzyl O-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)(1->4)-2-O-benzoyl-6-O-benzyl-α-D-glucopyranoside-3,6-phthalate

Chemical Property:

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Technology Process of benzyl O-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)(1->4)-2-O-benzoyl-6-O-benzyl-α-D-glucopyranoside-3,6-phthalate

There total 8 articles about benzyl O-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)(1->4)-2-O-benzoyl-6-O-benzyl-α-D-glucopyranoside-3,6-phthalate 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: 69.0%

phenyl 2,3,4-tri-O-benzyl-6-O-[(2-O-benzoyl-1,6-di-O-benzyl-α-D-glucopyranos-3-yloxy)-2-carbonylbenzoyl]-1-thio-α-D-mannopyranoside (262605-60-7) → benzyl O-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)(1->4)-2-O-benzoyl-6-O-benzyl-α-D-glucopyranoside-3,6-phthalate (262605-66-3) + benzyl O-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)(1->4)-2-O-benzoyl-6-O-benzyl-α-D-glucopyranoside-3,6-phthalate (262605-65-2)

Guidance literature:

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In acetonitrile; at -30 ℃; for 0.166667h;

DOI:10.1016/S0040-4020(99)01053-4

Reference yield:

phthalic anhydride (85-44-9) → benzyl O-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)(1->4)-2-O-benzoyl-6-O-benzyl-α-D-glucopyranoside-3,6-phthalate (262605-65-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / DMAO / pyridine / 15 h / 20 °C

2: 70 percent / DCC; DMAP; p-TsOH / pyridine / 24 h / 20 °C

3: 83 percent / HCl/Et₂O; NaCNBH₃ / tetrahydrofuran

4: 69 percent / 4A molecular sieves; NIS; TMSOTf / acetonitrile / 0.17 h / -30 °C

With hydrogenchloride; dmap; N-iodo-succinimide; diethyl ether; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium cyanoborohydride; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; pyridine; acetonitrile; 1: Acylation / 2: Esterification / 3: Ring cleavage / 4: Cyclization;

DOI:10.1016/S0040-4020(99)01053-4

Reference yield:

benzyl bromide (100-39-0) → benzyl O-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)(1->4)-2-O-benzoyl-6-O-benzyl-α-D-glucopyranoside-3,6-phthalate (262605-65-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 9.0 g / NaH / dimethylformamide / 3 h / 20 °C

2: 61 percent / aq. HCl / acetone / 24 h / 60 °C

3: 90 percent / DMAO / pyridine / 15 h / 20 °C

4: 70 percent / DCC; DMAP; p-TsOH / pyridine / 24 h / 20 °C

5: 83 percent / HCl/Et₂O; NaCNBH₃ / tetrahydrofuran

6: 69 percent / 4A molecular sieves; NIS; TMSOTf / acetonitrile / 0.17 h / -30 °C

With hydrogenchloride; dmap; N-iodo-succinimide; diethyl ether; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; pyridine; N,N-dimethyl-formamide; acetone; acetonitrile; 1: Alkylation / 2: Substitution / 3: Acylation / 4: Esterification / 5: Ring cleavage / 6: Cyclization;

DOI:10.1016/S0040-4020(99)01053-4

upstream raw materials:

phenyl 2,3,4-tri-O-benzyl-6-O-[(2-O-benzoyl-1,6-di-O-benzyl-α-D-glucopyranos-3-yloxy)-2-carbonylbenzoyl]-1-thio-α-D-mannopyranoside

phthalic anhydride

benzyl bromide

phenyl 2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranoside

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