benzyl 5-O-pivaloyl-2-O-methoxymethyl-3-deoxy-3-C-hydroxymethyl-α-D-lyxo-pentofuranose

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Chemical Name:benzyl 5-O-pivaloyl-2-O-methoxymethyl-3-deoxy-3-C-hydroxymethyl-α-D-lyxo-pentofuranose
CAS No.:288380-76-7
Molecular Formula:C₂₀H₃₀O₇
Molecular Weight:382.454
Hs Code.:

Synonyms:benzyl 5-O-pivaloyl-2-O-methoxymethyl-3-deoxy-3-C-hydroxymethyl-α-D-lyxo-pentofuranose

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Chemical Property of benzyl 5-O-pivaloyl-2-O-methoxymethyl-3-deoxy-3-C-hydroxymethyl-α-D-lyxo-pentofuranose

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Technology Process of benzyl 5-O-pivaloyl-2-O-methoxymethyl-3-deoxy-3-C-hydroxymethyl-α-D-lyxo-pentofuranose

There total 9 articles about benzyl 5-O-pivaloyl-2-O-methoxymethyl-3-deoxy-3-C-hydroxymethyl-α-D-lyxo-pentofuranose 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: 85.0%

: 288380-92-7
benzyl 3-deoxy-3-C-methylene-2-O-methoxymethyl-5-O-pivaloyl-α-D-lyxo-pentofuranoside

: 288380-76-7
benzyl 5-O-pivaloyl-2-O-methoxymethyl-3-deoxy-3-C-hydroxymethyl-α-D-lyxo-pentofuranose

Guidance literature:: benzyl 3-deoxy-3-C-methylene-2-O-methoxymethyl-5-O-pivaloyl-α-D-lyxo-pentofuranoside; With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran;

With sodium hydroxide; dihydrogen peroxide;
DOI:10.1016/S0960-894X(00)00189-X

Reference yield:

: 55174-92-0
1,2-O-isopropylidene-5-O-2,2-dimethylpropanoyl-α-D-erythro-pent-3-ulofuranose

: 288380-76-7
benzyl 5-O-pivaloyl-2-O-methoxymethyl-3-deoxy-3-C-hydroxymethyl-α-D-lyxo-pentofuranose

Guidance literature:: Multi-step reaction with 6 steps

1.1: 85 percent / NaHMDS / tetrahydrofuran / 1.5 h / -78 - 20 °C

2.1: 58 percent / 4 M HCl / toluene; dioxane / 16 h / 0 - 20 °C

3.1: PPh₃; azodicarboxylic acid diethyl ester / tetrahydrofuran; toluene / 3.25 h / 0 - 20 °C

4.1: 1.67 g / NaOH / methanol; H₂O / 1 h / 0 °C

5.1: 88 percent / iPr₂NEt; Bu₄NI / CH₂Cl₂ / 14 h / 0 - 20 °C

6.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 50 °C

6.2: 85 percent / 3 M NaOH; 30percent H₂O₂ / H₂O; tetrahydrofuran / 2 h / 20 °C

With hydrogenchloride; sodium hydroxide; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; toluene; 1.1: Wittig reaction / 3.1: Mitsunobu reaction;
DOI:10.1021/jo010375i

Reference yield:

: 55174-91-9
(-)-1,2-O-isopropylidene-5-O-pivaloyl-α-D-xylofuranose

: 288380-76-7
benzyl 5-O-pivaloyl-2-O-methoxymethyl-3-deoxy-3-C-hydroxymethyl-α-D-lyxo-pentofuranose

Guidance literature:: Multi-step reaction with 7 steps

1.1: 98 percent / 4 Angstroem molecular sieves; pyridinium chlorochromate / CH₂Cl₂ / 3 h / 20 °C

2.1: 85 percent / NaHMDS / tetrahydrofuran / 1.5 h / -78 - 20 °C

3.1: 58 percent / 4 M HCl / toluene; dioxane / 16 h / 0 - 20 °C

4.1: PPh₃; azodicarboxylic acid diethyl ester / tetrahydrofuran; toluene / 3.25 h / 0 - 20 °C

5.1: 1.67 g / NaOH / methanol; H₂O / 1 h / 0 °C

6.1: 88 percent / iPr₂NEt; Bu₄NI / CH₂Cl₂ / 14 h / 0 - 20 °C

7.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 50 °C

7.2: 85 percent / 3 M NaOH; 30percent H₂O₂ / H₂O; tetrahydrofuran / 2 h / 20 °C

With hydrogenchloride; sodium hydroxide; 4 A molecular sieve; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; pyridinium chlorochromate; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; toluene; 2.1: Wittig reaction / 4.1: Mitsunobu reaction;
DOI:10.1021/jo010375i