phenyl 2^I,3^I,2^II,3^II-tetra-O-benzyl-4^II,6^II-O-benzylidene-6^I-O-tert-butyldiphenylsilyl-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-tert-butyldiphenylsilyl-1^I-thio-β-maltoside
• CAS No.: 259742-11-5
• Molecular Formula: C₆₉H₇₂O₁₀SSi
• Molecular Weight: 1121.48

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

There total 7 articles about phenyl 2^I,3^I,2^II,3^II-tetra-O-benzyl-4^II,6^II-O-benzylidene-6^I-O-tert-butyldiphenylsilyl-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: 56.0%

benzyl bromide (100-39-0) + Phenyl 4-O-(4,6-O-benzylidene-α-D-glucopyranosyl)-6-O-tert-butyldiphenylsilyl-1-thio-β-D-glucopyranoside (309913-15-3) → phenyl 2I,3I,2II,3II-tetra-O-benzyl-4II,6II-O-benzylidene-6I-O-tert-butyldiphenylsilyl-1I-thio-β-maltoside (259742-11-5)

Guidance literature:

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In toluene; at 20 ℃; for 72h;

DOI:10.1055/s-2000-7601

Reference yield:

phenyl 4-O-(4,6-O-benzylidene-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside (87470-75-5) → phenyl 2I,3I,2II,3II-tetra-O-benzyl-4II,6II-O-benzylidene-6I-O-tert-butyldiphenylsilyl-1I-thio-β-maltoside (259742-11-5)

Guidance literature:

Multi-step reaction with 2 steps

1: DMAP; pyridine / dimethylformamide / 20 °C

2: 20.2 g / NaH / dimethylformamide / 20 °C

With pyridine; dmap; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1021/jo025887r

Reference yield:

phenylthiotrimethylsilane (4551-15-9) → phenyl 2I,3I,2II,3II-tetra-O-benzyl-4II,6II-O-benzylidene-6I-O-tert-butyldiphenylsilyl-1I-thio-β-maltoside (259742-11-5)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1021/jo025887r

upstream raw materials:

benzyl bromide

Phenyl 4-O-(4,6-O-benzylidene-α-D-glucopyranosyl)-6-O-tert-butyldiphenylsilyl-1-thio-β-D-glucopyranoside

phenylthiotrimethylsilane

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

Downstream raw materials:

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

Phenyl 2,3-di-O-benzyl-4-O-(4,6-di-O-benzylidene-2,3-di-O-benzyl-α-D-glucopyranosyl)-6-O-(4-phenylbenzoyl)-1-thio-β-D-glucopyranoside

Phenyl 2,3-di-O-benzyl-6-O-chloroacetyl-4-O-(4,6-di-O-benzylidene-2,3-di-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

Phenyl 2,3-di-O-benzyl-6-O-bromoacetyl-4-O-(4,6-di-O-benzylidene-2,3-di-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

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