phenyl 2^I,3^I,2^II,3^II-tetra-O-benzyl-4^II,6^II-O-benzylidene-6^I-O-(2-carboxybenzoyl)-1^I-thio-β-maltoside

Base Information

• Chemical Name: phenyl 2^I,3^I,2^II,3^II-tetra-O-benzyl-4^II,6^II-O-benzylidene-6^I-O-(2-carboxybenzoyl)-1^I-thio-β-maltoside
• CAS No.: 259742-12-6
• Molecular Formula: C₆₁H₅₈O₁₃S
• Molecular Weight: 1031.19

Synonyms:phenyl 2^I,3^I,2^II,3^II-tetra-O-benzyl-4^II,6^II-O-benzylidene-6^I-O-(2-carboxybenzoyl)-1^I-thio-β-maltoside

Chemical Property of phenyl 2^I,3^I,2^II,3^II-tetra-O-benzyl-4^II,6^II-O-benzylidene-6^I-O-(2-carboxybenzoyl)-1^I-thio-β-maltoside

Chemical Property:

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Technology Process of phenyl 2^I,3^I,2^II,3^II-tetra-O-benzyl-4^II,6^II-O-benzylidene-6^I-O-(2-carboxybenzoyl)-1^I-thio-β-maltoside

There total 11 articles about phenyl 2^I,3^I,2^II,3^II-tetra-O-benzyl-4^II,6^II-O-benzylidene-6^I-O-(2-carboxybenzoyl)-1^I-thio-β-maltoside 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: 100.0%

phthalic anhydride (85-44-9) + phenyl 2I,3I,2II,3II-tetra-O-benzyl-4II,6II-O-benzylidene-1I-thio-β-maltoside (259742-19-3) → phenyl 2I,3I,2II,3II-tetra-O-benzyl-4II,6II-O-benzylidene-6I-O-(2-carboxybenzoyl)-1I-thio-β-maltoside (259742-12-6)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1055/s-1999-2997

Reference yield:

phenylthiotrimethylsilane (4551-15-9) → phenyl 2I,3I,2II,3II-tetra-O-benzyl-4II,6II-O-benzylidene-6I-O-(2-carboxybenzoyl)-1I-thio-β-maltoside (259742-12-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 83 percent / ZnI₂ / 1,2-dichloro-ethane / 20 °C

2: MeONa / methanol / 4 h / 20 °C

3: TsOH*H₂O / dimethylformamide / 3 h / 60 °C / 15 Torr

4: DMAP; pyridine / dimethylformamide / 20 °C

5: 20.2 g / NaH / dimethylformamide / 20 °C

6: TBAF / tetrahydrofuran / 2.5 h / 20 °C

7: 100 percent / Et₃N / CH₂Cl₂ / 20 °C

With pyridine; dmap; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; toluene-4-sulfonic acid; triethylamine; zinc(II) iodide; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/jo025887r

Reference yield:

phenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside (5346-81-6,28022-13-1,28022-14-2) → phenyl 2I,3I,2II,3II-tetra-O-benzyl-4II,6II-O-benzylidene-6I-O-(2-carboxybenzoyl)-1I-thio-β-maltoside (259742-12-6)

Guidance literature:

Multi-step reaction with 6 steps

1: MeONa / methanol / 4 h / 20 °C

2: TsOH*H₂O / dimethylformamide / 3 h / 60 °C / 15 Torr

3: DMAP; pyridine / dimethylformamide / 20 °C

4: 20.2 g / NaH / dimethylformamide / 20 °C

5: TBAF / tetrahydrofuran / 2.5 h / 20 °C

6: 100 percent / Et₃N / CH₂Cl₂ / 20 °C

With pyridine; dmap; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo025887r

upstream raw materials:

phthalic anhydride

phenyl 2^I,3^I,2^II,3^II-tetra-O-benzyl-4^II,6^II-O-benzylidene-1^I-thio-β-maltoside

phenylthiotrimethylsilane

1,2,3,6,2',3',4',6'-octa-O-acetylmaltose

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