methyl 2,5-anhydro-6-O-benzyl-3,4-O-isopropylidene-2-ureido-β-D-ribo-2-hexulofuranosonate

Base Information

Chemical Name:methyl 2,5-anhydro-6-O-benzyl-3,4-O-isopropylidene-2-ureido-β-D-ribo-2-hexulofuranosonate
CAS No.:339540-30-6
Molecular Formula:C₁₈H₂₄N₂O₇
Molecular Weight:380.398
Hs Code.:

Synonyms:methyl 2,5-anhydro-6-O-benzyl-3,4-O-isopropylidene-2-ureido-β-D-ribo-2-hexulofuranosonate

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Chemical Property of methyl 2,5-anhydro-6-O-benzyl-3,4-O-isopropylidene-2-ureido-β-D-ribo-2-hexulofuranosonate

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Technology Process of methyl 2,5-anhydro-6-O-benzyl-3,4-O-isopropylidene-2-ureido-β-D-ribo-2-hexulofuranosonate

There total 8 articles about methyl 2,5-anhydro-6-O-benzyl-3,4-O-isopropylidene-2-ureido-β-D-ribo-2-hexulofuranosonate 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%

: 339540-29-3
methyl 2,5-anhydro-6-O-benzyl-3,4-O-isopropylidene-2-[3-N-(4-methoxybenzyl)ureido]-β-D-ribo-2-hexulofuranosonate

: 339540-30-6
methyl 2,5-anhydro-6-O-benzyl-3,4-O-isopropylidene-2-ureido-β-D-ribo-2-hexulofuranosonate

Guidance literature:: With ammonium cerium(IV) nitrate; In water; acetonitrile; at 20 ℃; for 0.333333h;
DOI:10.1016/S0008-6215(02)00217-3

Reference yield:

: 30725-00-9
2,3-O-isopropylidene-D-ribonic-γ-lactone

: 339540-30-6
methyl 2,5-anhydro-6-O-benzyl-3,4-O-isopropylidene-2-ureido-β-D-ribo-2-hexulofuranosonate

Guidance literature:: Multi-step reaction with 8 steps

1: 95 percent / NaH / dimethylformamide

2: 7.5 percent / P(NMe₂)3 / CH₂Cl₂

3: 54 percent / 4-chloroperoxybenzoic acid; hydroquinone / CH₂Cl₂ / 16 h / 20 °C

4: 95 percent / NaN₃ / dimethylformamide / 5 h / 20 °C

5: tetrahydrofuran / 2 h / 24 °C

6: 904 mg / tetrahydrofuran / 72 h / 20 °C

7: 100 percent / HCl; water / tetrahydrofuran / 0.67 h / 20 °C

8: 97 percent / ammonium cerium(IV) nitrate / acetonitrile; H₂O / 0.33 h / 20 °C

With hydrogenchloride; sodium azide; ammonium cerium(IV) nitrate; p-chloroperbenzoic acid; water; sodium hydride; hydroquinone; Hexamethylphosphorous triamide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0008-6215(02)00217-3

Reference yield:

: 85846-80-6
5-O-benzyl-2,3-O-isopropylidene-D-ribono-1,4-lactone

: 339540-30-6
methyl 2,5-anhydro-6-O-benzyl-3,4-O-isopropylidene-2-ureido-β-D-ribo-2-hexulofuranosonate

Guidance literature:: Multi-step reaction with 7 steps

1: 7.5 percent / P(NMe₂)3 / CH₂Cl₂

2: 54 percent / 4-chloroperoxybenzoic acid; hydroquinone / CH₂Cl₂ / 16 h / 20 °C

3: 95 percent / NaN₃ / dimethylformamide / 5 h / 20 °C

4: tetrahydrofuran / 2 h / 24 °C

5: 904 mg / tetrahydrofuran / 72 h / 20 °C

6: 100 percent / HCl; water / tetrahydrofuran / 0.67 h / 20 °C

7: 97 percent / ammonium cerium(IV) nitrate / acetonitrile; H₂O / 0.33 h / 20 °C

With hydrogenchloride; sodium azide; ammonium cerium(IV) nitrate; p-chloroperbenzoic acid; water; hydroquinone; Hexamethylphosphorous triamide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0008-6215(02)00217-3