1,2,4,6-tetra-O-acetyl-3-O-benzyl-5-C-(tosyloxymethyl)-β-D-glucopyranose

Base Information

• Chemical Name: 1,2,4,6-tetra-O-acetyl-3-O-benzyl-5-C-(tosyloxymethyl)-β-D-glucopyranose
• CAS No.: 1338463-77-6
• Molecular Formula: C₂₉H₃₄O₁₃S
• Molecular Weight: 622.647

Synonyms:1,2,4,6-tetra-O-acetyl-3-O-benzyl-5-C-(tosyloxymethyl)-β-D-glucopyranose

Chemical Property of 1,2,4,6-tetra-O-acetyl-3-O-benzyl-5-C-(tosyloxymethyl)-β-D-glucopyranose

Chemical Property:

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Technology Process of 1,2,4,6-tetra-O-acetyl-3-O-benzyl-5-C-(tosyloxymethyl)-β-D-glucopyranose

There total 3 articles about 1,2,4,6-tetra-O-acetyl-3-O-benzyl-5-C-(tosyloxymethyl)-β-D-glucopyranose 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: 86.0%

1,2,4,6-tetra-O-acetyl-3-O-benzyl-5-C-(hydroxymethyl)-β-D-glucopyranose (1338463-76-5) + p-toluenesulfonyl chloride (98-59-9) → 1,2,4,6-tetra-O-acetyl-3-O-benzyl-5-C-(tosyloxymethyl)-β-D-glucopyranose (1338463-77-6)

Guidance literature:

With pyridine; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1021/ol2025229

Reference yield:

C22H26O11 → 1,2,4,6-tetra-O-acetyl-3-O-benzyl-5-C-(tosyloxymethyl)-β-D-glucopyranose (1338463-77-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate / ethanol; dichloromethane / 1 h / -78 - 20 °C / Inert atmosphere

2: pyridine / 18 h / 20 °C / Inert atmosphere

With pyridine; sodium tetrahydroborate; In ethanol; dichloromethane;

DOI:10.1021/ol2025229

Reference yield:

1,2,4,6-tetra-O-acetyl-3-O-benzyl-5-C-vinyl-β-D-glucopyranoside (612841-73-3) → 1,2,4,6-tetra-O-acetyl-3-O-benzyl-5-C-(tosyloxymethyl)-β-D-glucopyranose (1338463-77-6)

Guidance literature:

Multi-step reaction with 3 steps

1: ozone / ethanol; dichloromethane / 3 h / -78 °C

2: sodium tetrahydroborate / ethanol; dichloromethane / 1 h / -78 - 20 °C / Inert atmosphere

3: pyridine / 18 h / 20 °C / Inert atmosphere

With pyridine; sodium tetrahydroborate; ozone; In ethanol; dichloromethane;

DOI:10.1021/ol2025229

upstream raw materials:

1,2,4,6-tetra-O-acetyl-3-O-benzyl-5-C-(hydroxymethyl)-β-D-glucopyranose

p-toluenesulfonyl chloride

1,2,4,6-tetra-O-acetyl-3-O-benzyl-5-C-vinyl-β-D-glucopyranoside

Downstream raw materials:

1-{3-deoxy-6-O-(4,4'-dimethoxytrityl)-2-O,5-C-methylene-β-D-glucopyranosyl}thymine

1-[4-O-{2-cyanoethoxy(diisopropylamino)phosphino}-3-deoxy-6-O-(4,4'-dimethoxytrityl)-2-O,5-C-methylene-β-D-glucopyranosyl]thymine

1-{2,4,6-tri-O-acetyl-3-O-(phenoxythiocarbonyl)-5-C-(tosyloxymethyl)-β-D-glucopyranosyl}thymine

1-{2,4,6-tri-O-acetyl-3-deoxy-5-C-(tosyloxymethyl)-β-D-glucopyranosyl}thymine

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