3-O-Benzyl-5,6-(benzyloxycarbonylepimino)-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco-furanose

Base Information

Chemical Name:3-O-Benzyl-5,6-(benzyloxycarbonylepimino)-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco-furanose
CAS No.:152554-17-1
Molecular Formula:C₂₄H₂₇NO₆
Molecular Weight:425.481
Hs Code.:

Synonyms:3-O-Benzyl-5,6-(benzyloxycarbonylepimino)-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco-furanose

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Chemical Property of 3-O-Benzyl-5,6-(benzyloxycarbonylepimino)-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco-furanose

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Technology Process of 3-O-Benzyl-5,6-(benzyloxycarbonylepimino)-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco-furanose

There total 6 articles about 3-O-Benzyl-5,6-(benzyloxycarbonylepimino)-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco-furanose 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%

: 501-53-1,94274-21-2
benzyl chloroformate

: 3-O-Benzyl-5,6-dideoxy-5,6-epimino-1,2-O-isopropylidene-α-D-gluco-furanose

: 152554-17-1
3-O-Benzyl-5,6-(benzyloxycarbonylepimino)-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco-furanose

Guidance literature:: With sodium hydrogencarbonate; In 1,4-dioxane; water; at 20 ℃;
DOI:10.1002/recl.19931120704

Reference yield:

: 42926-89-6
1,2-O-isopropylidene-3-O-benzyl-α-D-glucofuranose

: 152554-17-1
3-O-Benzyl-5,6-(benzyloxycarbonylepimino)-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco-furanose

Guidance literature:: Multi-step reaction with 4 steps

1: SOCl₂, pyridine / ethyl acetate / 0.25 h / 0 °C

2: NaIO₄ / RuCl₃ / CH₂Cl₂; acetonitrile; H₂O / 0.25 h / 20 °C

3: 1.) LiN₃, 2.) LiAlH₄ / 1.) THF, reflux, 2 h, 2.) THF, reflux, 5 h

4: 94 percent / NaHCO₃ / dioxane; H₂O / 20 °C

With pyridine; sodium periodate; lithium aluminium tetrahydride; thionyl chloride; lithium azide; sodium hydrogencarbonate; ruthenium trichloride; In 1,4-dioxane; dichloromethane; water; ethyl acetate; acetonitrile;
DOI:10.1002/recl.19931120704

Reference yield:

: 23558-05-6
3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

: 152554-17-1
3-O-Benzyl-5,6-(benzyloxycarbonylepimino)-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco-furanose

Guidance literature:: Multi-step reaction with 6 steps

1: 70 percent / tetrahydrofuran / 2 h / -20 °C

2: 78 percent / NaOAc, NaBr, CH₃CO₃H / acetic acid / 2 h / 0 °C

3: SOCl₂, pyridine / ethyl acetate / 0.25 h / 0 °C

4: NaIO₄ / RuCl₃ / CH₂Cl₂; acetonitrile; H₂O / 0.25 h / 20 °C

5: 1.) LiN₃, 2.) LiAlH₄ / 1.) THF, reflux, 2 h, 2.) THF, reflux, 5 h

6: 94 percent / NaHCO₃ / dioxane; H₂O / 20 °C

With pyridine; peracetic acid; sodium periodate; lithium aluminium tetrahydride; thionyl chloride; lithium azide; sodium acetate; sodium hydrogencarbonate; sodium bromide; ruthenium trichloride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetic acid; ethyl acetate; acetonitrile;
DOI:10.1002/recl.19931120704