tetraethyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-L-xylofuranose-6,6'-diyl]bisphosphonate

Base Information

Chemical Name:tetraethyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-L-xylofuranose-6,6'-diyl]bisphosphonate
CAS No.:391201-59-5
Molecular Formula:C₂₄H₄₀O₁₀P₂
Molecular Weight:550.523
Hs Code.:

Synonyms:tetraethyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-L-xylofuranose-6,6'-diyl]bisphosphonate

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Chemical Property of tetraethyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-L-xylofuranose-6,6'-diyl]bisphosphonate

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Technology Process of tetraethyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-L-xylofuranose-6,6'-diyl]bisphosphonate

There total 6 articles about tetraethyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-L-xylofuranose-6,6'-diyl]bisphosphonate 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:

: 1660-94-2
Tetraethyl methylenediphosphonate

: 391201-58-4
3-O-benzyl-1,2-O-isopropylidene-5-O-trifluoromethanesulfonyl-α-L-xylofuranose

: 391201-59-5
tetraethyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-L-xylofuranose-6,6'-diyl]bisphosphonate

Guidance literature:: Tetraethyl methylenediphosphonate; With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃;

3-O-benzyl-1,2-O-isopropylidene-5-O-trifluoromethanesulfonyl-α-L-xylofuranose; In N,N-dimethyl-formamide; at 20 ℃;
DOI:10.1016/S0040-4020(01)00885-7

Reference yield:

: 41546-31-0
L-xylose

: 391201-59-5
tetraethyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-L-xylofuranose-6,6'-diyl]bisphosphonate

Guidance literature:: Multi-step reaction with 6 steps

1.1: conc. H₂SO₄ / 3 h / 0 °C

1.2: 80 percent / aq. HCl / methanol / 20 °C

2.1: 91 percent / imidazole / CH₂Cl₂ / 24 h / 20 °C

3.1: 92 percent / NaH / dimethylformamide / 1 h / 20 °C

4.1: 98 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

5.1: 96 percent / pyridine / CH₂Cl₂ / 1 h / -30 °C

6.1: NaH / dimethylformamide / 0 - 20 °C

6.2: 2.87 g / dimethylformamide / 20 °C

With pyridine; 1H-imidazole; sulfuric acid; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)00885-7

Reference yield:

: 114861-22-2
1,2-O-isopropylidene-α-L-xylofuranose

: 391201-59-5
tetraethyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-L-xylofuranose-6,6'-diyl]bisphosphonate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 91 percent / imidazole / CH₂Cl₂ / 24 h / 20 °C

2.1: 92 percent / NaH / dimethylformamide / 1 h / 20 °C

3.1: 98 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

4.1: 96 percent / pyridine / CH₂Cl₂ / 1 h / -30 °C

5.1: NaH / dimethylformamide / 0 - 20 °C

5.2: 2.87 g / dimethylformamide / 20 °C

With pyridine; 1H-imidazole; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)00885-7