4-O-(6-O-trityl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3:5,6-di-O-isopropylidene-D-glucose dimethyl acetal

Base Information

• Chemical Name: 4-O-(6-O-trityl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3:5,6-di-O-isopropylidene-D-glucose dimethyl acetal
• CAS No.: 76888-25-0
• Molecular Formula: C₄₂H₅₄O₁₂
• Molecular Weight: 750.884

Synonyms:4-O-(6-O-trityl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3:5,6-di-O-isopropylidene-D-glucose dimethyl acetal

Chemical Property of 4-O-(6-O-trityl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3:5,6-di-O-isopropylidene-D-glucose dimethyl acetal

Chemical Property:

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Technology Process of 4-O-(6-O-trityl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3:5,6-di-O-isopropylidene-D-glucose dimethyl acetal

There total 1 articles about 4-O-(6-O-trityl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3:5,6-di-O-isopropylidene-D-glucose dimethyl acetal 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: 37.0%

2,3:5,6-Di-O-isopropylidene-4-O-(3',4'-O-isopropylidene-β-D-galactopyranosyl)-aldehydo-D-glucose dimethyl acetal (72200-51-2) + trityl chloride (76-83-5) → 4-O-(6-O-trityl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3:5,6-di-O-isopropylidene-D-glucose dimethyl acetal (76888-25-0)

Guidance literature:

With pyridine; dmap; at 65 ℃; for 4h;

Reference yield: 98.0%

4-O-(6-O-trityl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3:5,6-di-O-isopropylidene-D-glucose dimethyl acetal (76888-25-0) → 4-O-(3,4-O-isopropylidene-6-O-trityl-β-D-lyxo-hexopyranosyl-2-ulose)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal (263845-18-7)

Guidance literature:

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; In dichloromethane; at 20 ℃; for 3.5h;

DOI:10.1080/07328300008544066

Reference yield:

4-O-(6-O-trityl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3:5,6-di-O-isopropylidene-D-glucose dimethyl acetal (76888-25-0) → (E)-4-O-(2-deoxy-3,4-O-isopropylidene-2-methoxyimino-6-O-trityl-β-D-lyxo-hexopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / NMO; TPAP; powdered 4 Angstroem molecular sieves / CH₂Cl₂ / 3.5 h / 20 °C

2: pyridine / 20 °C

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; In pyridine; dichloromethane; 1: Oxidation / 2: Condensation;

DOI:10.1080/07328300008544066

upstream raw materials:

2,3:5,6-Di-O-isopropylidene-4-O-(3',4'-O-isopropylidene-β-D-galactopyranosyl)-aldehydo-D-glucose dimethyl acetal

trityl chloride

Downstream raw materials:

2'-O-acetyl-2,3:5,6:3',4'-tri-O-isopropylidene-6'-O-trityllactose dimethyl acetal

2,3:5,6:3',4'-tri-O-isopropylidene-2'-O-sulfo-6'-O-trityllactose dimethyl acetal triethylammonium salt

4-O-(3,4-O-isopropylidene-6-O-trityl-β-D-lyxo-hexopyranosyl-2-ulose)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

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