3,4-di-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-6-O-levulinyl-D-glucopyranose-1-dibutylphosphate

Base Information

Chemical Name:3,4-di-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-6-O-levulinyl-D-glucopyranose-1-dibutylphosphate
CAS No.:503181-10-0
Molecular Formula:C₃₁H₄₆NO₁₄P
Molecular Weight:687.678
Hs Code.:

Synonyms:3,4-di-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-6-O-levulinyl-D-glucopyranose-1-dibutylphosphate

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Chemical Property of 3,4-di-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-6-O-levulinyl-D-glucopyranose-1-dibutylphosphate

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Technology Process of 3,4-di-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-6-O-levulinyl-D-glucopyranose-1-dibutylphosphate

There total 9 articles about 3,4-di-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-6-O-levulinyl-D-glucopyranose-1-dibutylphosphate 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: 72.0%

: 107-66-4
dibutyl phosphate

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

: 503181-10-0
3,4-di-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-6-O-levulinyl-D-glucopyranose-1-dibutylphosphate

Guidance literature:: In toluene; for 14h;
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

: 503181-10-0
3,4-di-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-6-O-levulinyl-D-glucopyranose-1-dibutylphosphate

Guidance literature:: Multi-step reaction with 9 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

9: 72 percent / toluene / 14 h

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; toluene; acetonitrile;
DOI:10.1016/S0008-6215(02)00299-9

Reference yield:

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

: 503181-10-0
3,4-di-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-6-O-levulinyl-D-glucopyranose-1-dibutylphosphate

Guidance literature:: Multi-step reaction with 7 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

7: 72 percent / toluene / 14 h

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