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

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-carbonate
• CAS No.: 262605-63-0
• Molecular Formula: C₅₅H₅₄O₁₃
• Molecular Weight: 923.026

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-carbonate

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-carbonate

Chemical Property:

Purity/Quality:

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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-carbonate

There total 9 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-carbonate 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: 79.0%

phenyl 2,3,4-tri-O-benzyl-6-O-[(2-O-benzoyl-1,6-di-O-benzyl-α-D-glucopyranos-3-yloxy)-carbonyl]-1-sulfoxy-α-D-mannopyranoside (262605-36-7) → benzyl O-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)(1->4)-2-O-benzoyl-6-O-benzyl-α-D-glucopyranoside-3,6-carbonate (262605-63-0)

Guidance literature:

With trifluoromethylsulfonic anhydride; In dichloromethane; at 20 ℃; for 50h;

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-carbonate (262605-63-0)

Guidance literature:

Multi-step reaction with 7 steps

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

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

3: 94 percent / pyridine / toluene / 17 h / 20 °C

4: 81 percent / pyridine / CH₂Cl₂ / 20 h / 20 °C

5: 87 percent / HCl/Et₂O; NaCNBH₃ / tetrahydrofuran

6: 80 percent / m-chloroperbenoic acid / CH₂Cl₂ / 24 h / 20 °C

7: 79 percent / Tf₂O / CH₂Cl₂ / 50 h / 20 °C

With pyridine; hydrogenchloride; diethyl ether; trifluoromethylsulfonic anhydride; sodium hydride; sodium cyanoborohydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1: Alkylation / 2: Substitution / 3: Acylation / 4: Acylation / 5: Ring cleavage / 6: Oxidation / 7: Cyclization;

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

Reference yield:

(2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol (2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-63-1,105088-17-3,149495-84-1,77481-62-0) → benzyl O-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)(1->4)-2-O-benzoyl-6-O-benzyl-α-D-glucopyranoside-3,6-carbonate (262605-63-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 7.65 g / pyridine / 24 h / 20 °C

2: 9.0 g / NaH / dimethylformamide / 3 h / 20 °C

3: 61 percent / aq. HCl / acetone / 24 h / 60 °C

4: 94 percent / pyridine / toluene / 17 h / 20 °C

5: 81 percent / pyridine / CH₂Cl₂ / 20 h / 20 °C

6: 87 percent / HCl/Et₂O; NaCNBH₃ / tetrahydrofuran

7: 80 percent / m-chloroperbenoic acid / CH₂Cl₂ / 24 h / 20 °C

8: 79 percent / Tf₂O / CH₂Cl₂ / 50 h / 20 °C

With pyridine; hydrogenchloride; diethyl ether; trifluoromethylsulfonic anhydride; sodium hydride; sodium cyanoborohydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1: Substitution / 2: Alkylation / 3: Substitution / 4: Acylation / 5: Acylation / 6: Ring cleavage / 7: Oxidation / 8: 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)-carbonyl]-1-sulfoxy-α-D-mannopyranoside

benzyl bromide

(2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

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

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