5-benzamido-5-C-(hydroxymethyl)-5-deoxy-1,2-O-isopropylidene-β-L-ido-furanose 3,6-lactone

Base Information

Chemical Name:5-benzamido-5-C-(hydroxymethyl)-5-deoxy-1,2-O-isopropylidene-β-L-ido-furanose 3,6-lactone
CAS No.:148236-89-9
Molecular Formula:C₁₇H₁₉NO₇
Molecular Weight:349.34
Hs Code.:

Synonyms:5-benzamido-5-C-(hydroxymethyl)-5-deoxy-1,2-O-isopropylidene-β-L-ido-furanose 3,6-lactone

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Chemical Property of 5-benzamido-5-C-(hydroxymethyl)-5-deoxy-1,2-O-isopropylidene-β-L-ido-furanose 3,6-lactone

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Technology Process of 5-benzamido-5-C-(hydroxymethyl)-5-deoxy-1,2-O-isopropylidene-β-L-ido-furanose 3,6-lactone

There total 20 articles about 5-benzamido-5-C-(hydroxymethyl)-5-deoxy-1,2-O-isopropylidene-β-L-ido-furanose 3,6-lactone 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: 97.0%

: 5-benzamido-5-C-<(tert-butyldimethylsilyl)oxymethyl>-5-deoxy-1,2-O-isopropylidene-β-L-ido-furanose 3,6-lactone

: 148236-89-9
5-benzamido-5-C-(hydroxymethyl)-5-deoxy-1,2-O-isopropylidene-β-L-ido-furanose 3,6-lactone

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1016/S0040-4039(00)76967-X

Reference yield: 50.0%

: 98-88-4
benzoyl chloride

: 5-amino-5-deoxy-5-C-(hydroxymethyl)-1,2-O-isopropylidene-β-L-idofuranose-3,6-lactone

: 148236-89-9
5-benzamido-5-C-(hydroxymethyl)-5-deoxy-1,2-O-isopropylidene-β-L-ido-furanose 3,6-lactone

Guidance literature:: In methanol; at 20 ℃; for 36h;
DOI:10.1021/ol015930h

Reference yield:

: 106445-05-0
3-O-benzyl-6-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-α-D-xylo-hexofuran-5-ulose

: 148236-89-9
5-benzamido-5-C-(hydroxymethyl)-5-deoxy-1,2-O-isopropylidene-β-L-ido-furanose 3,6-lactone

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) diisopropylamine, n-butyllithium in hexane, 3.) sodium azide, 15-crown-5, N,N'-dimethylpropyleneurea / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 90 min, then to room temperature, 3.) THF, 70 deg C, 12 h

2: hydrogen / 10percent Pd/C / ethanol / 17 h / 2250.2 Torr

3: methanol / 48 h / Ambient temperature

4: 86 percent / DMSO, oxalyl chloride, triethylamine / CH₂Cl₂ / 1.5 h / -78 °C

5: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium azide; oxalyl dichloride; 15-crown-5; butyllithium; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane;