3,4-di-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-6-O-levulinyl-β-D-glucopyranosyl trichloroacetimidate

Base Information

Chemical Name:3,4-di-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-6-O-levulinyl-β-D-glucopyranosyl trichloroacetimidate
CAS No.:399524-38-0
Molecular Formula:C₂₅H₂₉Cl₃N₂O₁₁
Molecular Weight:639.871
Hs Code.:

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

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

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

There total 7 articles about 3,4-di-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-6-O-levulinyl-β-D-glucopyranosyl trichloroacetimidate 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:

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

: 399524-38-0
3,4-di-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-6-O-levulinyl-β-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 8 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

7: NBS; H₂O / acetonitrile / 13 h

8: 730 mg / CH₂Cl₂ / 2 h / 0 °C

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

Reference yield:

: 503180-98-1
4-pentenyl 2-benzyloxycarbonylamino-2-deoxy-β-D-glucopyranoside

: 399524-38-0
3,4-di-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-6-O-levulinyl-β-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / dimethylformamide / 14 h

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

3: 84 percent / TBAF; AcOH / tetrahydrofuran / 12 h

4: 94 percent / DMAP / pyridine; CH₂Cl₂ / 2 h

5: NBS; H₂O / acetonitrile / 13 h

6: 730 mg / CH₂Cl₂ / 2 h / 0 °C

With dmap; N-Bromosuccinimide; tetrabutyl ammonium fluoride; water; acetic acid; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0008-6215(02)00299-9

Reference yield:

: 503181-00-8
4-pentenyl 2-benzyloxycarbonylamino-2-deoxy-6-O-triisopropylsilyl-β-D-glucopyranoside

: 399524-38-0
3,4-di-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-6-O-levulinyl-β-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / DMAP / pyridine; CH₂Cl₂ / 2 h

2: 84 percent / TBAF; AcOH / tetrahydrofuran / 12 h

3: 94 percent / DMAP / pyridine; CH₂Cl₂ / 2 h

4: NBS; H₂O / acetonitrile / 13 h

5: 730 mg / CH₂Cl₂ / 2 h / 0 °C

With dmap; N-Bromosuccinimide; tetrabutyl ammonium fluoride; water; acetic acid; In tetrahydrofuran; pyridine; dichloromethane; acetonitrile;
DOI:10.1016/S0008-6215(02)00299-9