3-O-benzyl-1,2-O-isopropylidene-5-O-(tert-butyldiphenylsilyl)-β-L-arabinofuranose

Base Information

• Chemical Name: 3-O-benzyl-1,2-O-isopropylidene-5-O-(tert-butyldiphenylsilyl)-β-L-arabinofuranose
• CAS No.: 168103-01-3
• Molecular Formula: C₃₁H₃₈O₅Si
• Molecular Weight: 518.725

Synonyms:3-O-benzyl-1,2-O-isopropylidene-5-O-(tert-butyldiphenylsilyl)-β-L-arabinofuranose

Chemical Property of 3-O-benzyl-1,2-O-isopropylidene-5-O-(tert-butyldiphenylsilyl)-β-L-arabinofuranose

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

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Technology Process of 3-O-benzyl-1,2-O-isopropylidene-5-O-(tert-butyldiphenylsilyl)-β-L-arabinofuranose

There total 2 articles about 3-O-benzyl-1,2-O-isopropylidene-5-O-(tert-butyldiphenylsilyl)-β-L-arabinofuranose 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: 90.0%

benzyl bromide (100-39-0) + (3aR,5S,6S,6aR)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol (103763-14-0) → 3-O-benzyl-1,2-O-isopropylidene-5-O-(tert-butyldiphenylsilyl)-β-L-arabinofuranose (168103-01-3)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1016/j.carres.2007.07.010

Reference yield: 77.0%

benzyl chloride (100-44-7) + (3aR,5S,6S,6aR)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol (103763-14-0) → 3-O-benzyl-1,2-O-isopropylidene-5-O-(tert-butyldiphenylsilyl)-β-L-arabinofuranose (168103-01-3)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; for 2.5h; Ambient temperature;

DOI:10.1016/0040-4020(94)00978-4

Reference yield: 80.0%

3-O-benzyl-1,2-O-isopropylidene-5-O-(tert-butyldiphenylsilyl)-β-L-arabinofuranose (168103-01-3) → 3-O-benzyl-1,2-O-isopropylidene-β-L-arabinofuranose (68354-70-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1.5h; Ambient temperature;

DOI:10.1016/0040-4020(94)00978-4

upstream raw materials:

benzyl chloride

(3aR,5S,6S,6aR)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol

benzyl bromide

Downstream raw materials:

3-O-benzyl-1,2-O-isopropylidene-β-L-arabinofuranose

3-O-benzyl-5-deoxy-5-iodo-1,2-O-isopropylidene-β-L-arabinofuranose

5-O-benzoyl-3-O-benzyl-1,2-O-isopropylidene-β-L-arabinofuranose

1,2-di-O-acetyl-5-O-benzoyl-3-O-benzyl-L-arabinofuranose

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