ethyl 2-C-(benzoyloxy-1-oxoethyl)-2,3,6-trideoxy-α-D-threo-hexopyranosid-4-ulose

Base Information

Chemical Name:ethyl 2-C-(benzoyloxy-1-oxoethyl)-2,3,6-trideoxy-α-D-threo-hexopyranosid-4-ulose
CAS No.:57800-46-1
Molecular Formula:C₁₇H₂₀O₆
Molecular Weight:320.342
Hs Code.:

Synonyms:ethyl 2-C-(benzoyloxy-1-oxoethyl)-2,3,6-trideoxy-α-D-threo-hexopyranosid-4-ulose

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Chemical Property of ethyl 2-C-(benzoyloxy-1-oxoethyl)-2,3,6-trideoxy-α-D-threo-hexopyranosid-4-ulose

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Technology Process of ethyl 2-C-(benzoyloxy-1-oxoethyl)-2,3,6-trideoxy-α-D-threo-hexopyranosid-4-ulose

There total 12 articles about ethyl 2-C-(benzoyloxy-1-oxoethyl)-2,3,6-trideoxy-α-D-threo-hexopyranosid-4-ulose 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: 89.0%

: 76101-58-1
(2R,5S,6S)-6-Ethoxy-5-(2-hydroxy-acetyl)-2-methyl-dihydro-pyran-3-one

: 98-88-4
benzoyl chloride

: 57800-46-1
ethyl 2-C-(benzoyloxy-1-oxoethyl)-2,3,6-trideoxy-α-D-threo-hexopyranosid-4-ulose

Guidance literature:: With pyridine; at 0 ℃; for 12h;
DOI:10.1139/v80-429

Reference yield:

: 57800-44-9,76155-45-8,76155-46-9
(2R,5R,6S)-5-(1,2-Dihydroxy-ethyl)-6-ethoxy-2-trityloxymethyl-dihydro-pyran-3-one

: 57800-46-1
ethyl 2-C-(benzoyloxy-1-oxoethyl)-2,3,6-trideoxy-α-D-threo-hexopyranosid-4-ulose

Guidance literature:: Multi-step reaction with 9 steps

1: 94 percent / pyridine / 18 h / 0 °C

2: 2.66 g / hydrogen chloride / CHCl₃ / -30 °C

3: 3.71 g / pyridine / 24 h / 0 °C

4: 1.) sodium iodide, 2.) Raney nickel / 1.) methylethyl ketone, reflux, 2 h, 2.) acetone, reflux, 12 h

5: 98 percent / triethylamine, water / methanol / 4 h

6: 75 percent / pyridine / 48 h

7: 93 percent / Collin's reagent / CH₂Cl₂ / 0.5 h

8: 51 percent / hydrogen chloride / CHCl₃ / -30 °C

9: 89 percent / pyridine / 12 h / 0 °C

With pyridine; hydrogenchloride; water; dipyridine chromium trioxide; nickel; triethylamine; sodium iodide; In methanol; dichloromethane; chloroform;
DOI:10.1139/v80-429

Reference yield:

: 57800-45-0,76231-27-1,76231-28-2
(2R,5R,6S)-5-(1,2-Dihydroxy-ethyl)-6-ethoxy-2-methyl-dihydro-pyran-3-one

: 57800-46-1
ethyl 2-C-(benzoyloxy-1-oxoethyl)-2,3,6-trideoxy-α-D-threo-hexopyranosid-4-ulose

Guidance literature:: Multi-step reaction with 4 steps

1: 75 percent / pyridine / 48 h

2: 93 percent / Collin's reagent / CH₂Cl₂ / 0.5 h

3: 51 percent / hydrogen chloride / CHCl₃ / -30 °C

4: 89 percent / pyridine / 12 h / 0 °C

With pyridine; hydrogenchloride; dipyridine chromium trioxide; In dichloromethane; chloroform;
DOI:10.1139/v80-429