5-O-benzyl-1,2-O-isopropylidene-3-O-p-toluenesulfonyl-6-O-triphenylmethyl-α-D-glucofuranose

Base Information

• Chemical Name: 5-O-benzyl-1,2-O-isopropylidene-3-O-p-toluenesulfonyl-6-O-triphenylmethyl-α-D-glucofuranose
• CAS No.: 146329-35-3
• Molecular Formula: C₄₂H₄₂O₈S
• Molecular Weight: 706.857

Synonyms:5-O-benzyl-1,2-O-isopropylidene-3-O-p-toluenesulfonyl-6-O-triphenylmethyl-α-D-glucofuranose

Chemical Property of 5-O-benzyl-1,2-O-isopropylidene-3-O-p-toluenesulfonyl-6-O-triphenylmethyl-α-D-glucofuranose

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Technology Process of 5-O-benzyl-1,2-O-isopropylidene-3-O-p-toluenesulfonyl-6-O-triphenylmethyl-α-D-glucofuranose

There total 3 articles about 5-O-benzyl-1,2-O-isopropylidene-3-O-p-toluenesulfonyl-6-O-triphenylmethyl-α-D-glucofuranose 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: 92.0%

benzyl bromide (100-39-0) + 1,2-O-Isopropyliden-3-O-(4-methylphenylsulfonyl)-6-O-(triphenylmethyl)-α-D-glucofuranose (78785-12-3) → 5-O-benzyl-1,2-O-isopropylidene-3-O-p-toluenesulfonyl-6-O-triphenylmethyl-α-D-glucofuranose (146329-35-3)

Guidance literature:

With sodium hydride; methyl-triphenylphosphonium iodide; In tetrahydrofuran; for 18h; Ambient temperature;

DOI:10.1055/s-1992-26317

Reference yield:

trityl chloride (76-83-5) → 5-O-benzyl-1,2-O-isopropylidene-3-O-p-toluenesulfonyl-6-O-triphenylmethyl-α-D-glucofuranose (146329-35-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / pyridine / 6 h / 60 °C

2: 92 percent / 1) NaH / MePh₃PI / tetrahydrofuran / 18 h / Ambient temperature

With pyridine; sodium hydride; methyl-triphenylphosphonium iodide; In tetrahydrofuran;

DOI:10.1055/s-1992-26317

Reference yield:

(3aR,5R,6S,6aR)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate (2946-01-2) → 5-O-benzyl-1,2-O-isopropylidene-3-O-p-toluenesulfonyl-6-O-triphenylmethyl-α-D-glucofuranose (146329-35-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / pyridine / 6 h / 60 °C

2: 92 percent / 1) NaH / MePh₃PI / tetrahydrofuran / 18 h / Ambient temperature

With pyridine; sodium hydride; methyl-triphenylphosphonium iodide; In tetrahydrofuran;

DOI:10.1055/s-1992-26317

upstream raw materials:

benzyl bromide

1,2-O-Isopropyliden-3-O-(4-methylphenylsulfonyl)-6-O-(triphenylmethyl)-α-D-glucofuranose

trityl chloride

(3aR,5R,6S,6aR)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate

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