6-O-benzyl-2,3-dideoxy-4,5-O-bis(methoxymethyl)-3-(1,3-dioxo-2-azindan-2-yl)-L-lyxo-hexose ethylene acetal

Base Information

Chemical Name:6-O-benzyl-2,3-dideoxy-4,5-O-bis(methoxymethyl)-3-(1,3-dioxo-2-azindan-2-yl)-L-lyxo-hexose ethylene acetal
CAS No.:104465-63-6
Molecular Formula:C₂₇H₃₃NO₉
Molecular Weight:515.56
Hs Code.:

Synonyms:6-O-benzyl-2,3-dideoxy-4,5-O-bis(methoxymethyl)-3-(1,3-dioxo-2-azindan-2-yl)-L-lyxo-hexose ethylene acetal

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Chemical Property of 6-O-benzyl-2,3-dideoxy-4,5-O-bis(methoxymethyl)-3-(1,3-dioxo-2-azindan-2-yl)-L-lyxo-hexose ethylene acetal

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Technology Process of 6-O-benzyl-2,3-dideoxy-4,5-O-bis(methoxymethyl)-3-(1,3-dioxo-2-azindan-2-yl)-L-lyxo-hexose ethylene acetal

There total 2 articles about 6-O-benzyl-2,3-dideoxy-4,5-O-bis(methoxymethyl)-3-(1,3-dioxo-2-azindan-2-yl)-L-lyxo-hexose ethylene acetal 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: 94.0%

: 136918-14-4,85-41-6
phthalimide

: 104465-62-5
6-O-benzyl-2-deoxy-4,5-O-bis(methoxymethyl)-L-xylo-hexose ethylene acetal

: 104465-63-6
6-O-benzyl-2,3-dideoxy-4,5-O-bis(methoxymethyl)-3-(1,3-dioxo-2-azindan-2-yl)-L-lyxo-hexose ethylene acetal

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 14h; Ambient temperature;
DOI:10.1021/jo00372a026

Reference yield:

: 99878-63-4
4-O-benzyl-2,3-O-bis(methoxymethyl)-L-threose

: 104465-63-6
6-O-benzyl-2,3-dideoxy-4,5-O-bis(methoxymethyl)-3-(1,3-dioxo-2-azindan-2-yl)-L-lyxo-hexose ethylene acetal

Guidance literature:: Multi-step reaction with 2 steps

1: 70 percent / tetrahydrofuran / 14 h / Ambient temperature

2: 94 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 14 h / Ambient temperature

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;
DOI:10.1021/jo00372a026

Reference yield:

: 104465-63-6
6-O-benzyl-2,3-dideoxy-4,5-O-bis(methoxymethyl)-3-(1,3-dioxo-2-azindan-2-yl)-L-lyxo-hexose ethylene acetal

: 81176-31-0
N-Benzoyl-L-daunosamine

Guidance literature:: Multi-step reaction with 6 steps

1: 79 percent / H₂ / 10percent Pd/C / methanol / 14 h / 760 Torr

2: 99 percent / pyridine / 14 h / Ambient temperature

3: 97 percent / NaI / butan-2-one / 14 h / Heating

4: 89 percent / H₂, Et₃N / 10percent Pd/C / methanol / 20 h / 760 Torr

5: 1.) (NH₂)2*H₂O, 2.) aq. Na₂CO₃ / 1.) ethanol, reflux, 1.5 h, 2.) CH₂Cl₂, RT, 1 h

6: 57 percent / CF₃CO₂H / tetrahydrofuran; H₂O / 0.17 h / 50 °C

With pyridine; hydrogen; sodium carbonate; hydrazine hydrate; triethylamine; trifluoroacetic acid; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; water; butanone;
DOI:10.1021/jo00372a026