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

Base Information

Chemical Name:4-pentenyl 3,4-di-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-β-D-glucopyranoside
CAS No.:503181-04-2
Molecular Formula:C₂₃H₃₁NO₉
Molecular Weight:465.5
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

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

There total 5 articles about 4-pentenyl 3,4-di-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-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: 84.0%

: 503181-02-0
4-pentenyl 3,4-di-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-6-O-triisopropylsilyl-β-D-glucopyranoside

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

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; for 12h;
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

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

Guidance literature:: Multi-step reaction with 5 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

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

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

Guidance literature:: Multi-step reaction with 5 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

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