1,2-di-O-benzoyl-3-O-(diisopropylphosphonomethyl)-5-deoxy-5-chloromethylene-α,β-L-arabinofuranose

Base Information

Chemical Name:1,2-di-O-benzoyl-3-O-(diisopropylphosphonomethyl)-5-deoxy-5-chloromethylene-α,β-L-arabinofuranose
CAS No.:934497-30-0
Molecular Formula:C₂₇H₃₂ClO₉P
Molecular Weight:566.972
Hs Code.:

Synonyms:1,2-di-O-benzoyl-3-O-(diisopropylphosphonomethyl)-5-deoxy-5-chloromethylene-α,β-L-arabinofuranose

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Chemical Property of 1,2-di-O-benzoyl-3-O-(diisopropylphosphonomethyl)-5-deoxy-5-chloromethylene-α,β-L-arabinofuranose

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Technology Process of 1,2-di-O-benzoyl-3-O-(diisopropylphosphonomethyl)-5-deoxy-5-chloromethylene-α,β-L-arabinofuranose

There total 6 articles about 1,2-di-O-benzoyl-3-O-(diisopropylphosphonomethyl)-5-deoxy-5-chloromethylene-α,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: 86.0%

: 3-O-(diisopropylphosphonomethyl)-5-deoxy-5-chloromethylene-α,β-L-arabinofuranose

: 98-88-4
benzoyl chloride

: 934497-30-0
1,2-di-O-benzoyl-3-O-(diisopropylphosphonomethyl)-5-deoxy-5-chloromethylene-α,β-L-arabinofuranose

Guidance literature:: In pyridine; at 0 - 20 ℃;
DOI:10.1016/j.tet.2007.01.032

Reference yield:

: 134963-85-2
(diisopropoxyphosphoryl)methyl trifluoromethanesulfonate

: 934497-30-0
1,2-di-O-benzoyl-3-O-(diisopropylphosphonomethyl)-5-deoxy-5-chloromethylene-α,β-L-arabinofuranose

Guidance literature:: Multi-step reaction with 5 steps

1: 84 percent / sodium hydride / tetrahydrofuran; various solvent(s) / -78 - 20 °C

2: 99 percent / NaIO₄; H₅IO₆ / ethyl acetate / 5 h / 20 °C

3: n-BuLi / tetrahydrofuran; hexane / 3 h / 0 °C

4: 460 g / TFA / H₂O / 2 h / 20 °C

5: 86 percent / pyridine / 0 - 20 °C

With sodium periodate; n-butyllithium; sodium hydride; periodic acid; trifluoroacetic acid; In tetrahydrofuran; pyridine; hexane; water; ethyl acetate; 3: Wittig olefination;
DOI:10.1016/j.tet.2007.01.032

Reference yield:

: 934497-28-6
1,2-O-isopropylidene-3-O-(diisopropylphosphonomethyl)-5-oxo-β-L-arabinose

: 934497-30-0
1,2-di-O-benzoyl-3-O-(diisopropylphosphonomethyl)-5-deoxy-5-chloromethylene-α,β-L-arabinofuranose

Guidance literature:: Multi-step reaction with 3 steps

1: n-BuLi / tetrahydrofuran; hexane / 3 h / 0 °C

2: 460 g / TFA / H₂O / 2 h / 20 °C

3: 86 percent / pyridine / 0 - 20 °C

With n-butyllithium; trifluoroacetic acid; In tetrahydrofuran; pyridine; hexane; water; 1: Wittig olefination;
DOI:10.1016/j.tet.2007.01.032