4-pentenyl 3,4-di-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-6-O-levulinyl-β-D-glucopyranoside

Base Information

Chemical Name:4-pentenyl 3,4-di-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-6-O-levulinyl-β-D-glucopyranoside
CAS No.:503181-05-3
Molecular Formula:C₂₈H₃₇NO₁₁
Molecular Weight:563.602
Hs Code.:

Synonyms:4-pentenyl 3,4-di-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-6-O-levulinyl-β-D-glucopyranoside

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Chemical Property of 4-pentenyl 3,4-di-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-6-O-levulinyl-β-D-glucopyranoside

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Technology Process of 4-pentenyl 3,4-di-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-6-O-levulinyl-β-D-glucopyranoside

There total 6 articles about 4-pentenyl 3,4-di-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-6-O-levulinyl-β-D-glucopyranoside 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%

: 40608-06-8
levulinic anhydride

: 503181-04-2
4-pentenyl 3,4-di-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-β-D-glucopyranoside

: 503181-05-3
4-pentenyl 3,4-di-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-6-O-levulinyl-β-D-glucopyranoside

Guidance literature:: With dmap; In pyridine; dichloromethane; for 2h;
DOI:10.1016/S0008-6215(02)00299-9

Reference yield:

: 35946-66-8
2-(acetoxymethyl)-5-{[(benzyloxy)carbonyl]amino}tetrahydropyran-3,4,6-triyl triacetate

: 503181-05-3
4-pentenyl 3,4-di-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-6-O-levulinyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 54 percent / BF₃*Et₂O / CH₂Cl₂ / 48 h / 20 °C

2: 98 percent / NaOMe / methanol / 14 h

3: 95 percent / dimethylformamide / 14 h

4: 100 percent / DMAP / pyridine; CH₂Cl₂ / 2 h

5: 84 percent / TBAF; AcOH / tetrahydrofuran / 12 h

6: 94 percent / DMAP / pyridine; CH₂Cl₂ / 2 h

With dmap; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate; acetic acid; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(02)00299-9

Reference yield:

: 821-09-0
n-Pent-4-enyl alcohol

: 503181-05-3
4-pentenyl 3,4-di-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-6-O-levulinyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 54 percent / BF₃*Et₂O / CH₂Cl₂ / 48 h / 20 °C

2: 98 percent / NaOMe / methanol / 14 h

3: 95 percent / dimethylformamide / 14 h

4: 100 percent / DMAP / pyridine; CH₂Cl₂ / 2 h

5: 84 percent / TBAF; AcOH / tetrahydrofuran / 12 h

6: 94 percent / DMAP / pyridine; CH₂Cl₂ / 2 h

With dmap; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate; acetic acid; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(02)00299-9