5-N-benzyloxycarbonyl-3,4-di-O-benzyl-2,5-imino-2,5,6-trideoxy-L-iditol

Base Information

Chemical Name:5-N-benzyloxycarbonyl-3,4-di-O-benzyl-2,5-imino-2,5,6-trideoxy-L-iditol
CAS No.:287102-08-3
Molecular Formula:C₂₈H₃₁NO₅
Molecular Weight:461.558
Hs Code.:

Synonyms:5-N-benzyloxycarbonyl-3,4-di-O-benzyl-2,5-imino-2,5,6-trideoxy-L-iditol

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Chemical Property of 5-N-benzyloxycarbonyl-3,4-di-O-benzyl-2,5-imino-2,5,6-trideoxy-L-iditol

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Technology Process of 5-N-benzyloxycarbonyl-3,4-di-O-benzyl-2,5-imino-2,5,6-trideoxy-L-iditol

There total 10 articles about 5-N-benzyloxycarbonyl-3,4-di-O-benzyl-2,5-imino-2,5,6-trideoxy-L-iditol 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:

: 84608-23-1
3,4-O-isopropylidene-1-O-trityl-D-mannitol

: 287102-08-3
5-N-benzyloxycarbonyl-3,4-di-O-benzyl-2,5-imino-2,5,6-trideoxy-L-iditol

Guidance literature:: Multi-step reaction with 11 steps

1: pyridine / 12 h / 20 °C

2: 28.5 g / LiAlH₄ / tetrahydrofuran / 10 h / Heating

3: 46 percent / Et₃N / CH₂Cl₂ / 10 h / 0 °C

4: NaN₃ / hexamethylphosphoric acid triamide / 8 h / 80 °C

5: TPAP; N-methylmorpholine N-oxide / CH₂Cl₂ / 1 h / 20 °C

6: 2.03 g / TFA(80percent) / 1 h / 0 °C

7: Et₃N; 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 12 h / 20 °C

8: 1.08 g / H₂ / rhodium-alumina / ethanol / 3 h

9: K₂CO₃ / tetrahydrofuran; H₂O / 0.5 h / 0 °C

10: NaH / dimethylformamide / 10 h / 20 °C

11: 628 mg / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 0 °C

With pyridine; dmap; lithium aluminium tetrahydride; sodium azide; tetrapropylammonium perruthennate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; rhodium on alumina; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 1: Tosylation / 2: Reduction / 3: mesylation / 4: Substitution / 5: Oxidation / 6: Ring cleavage / 7: silylation / 8: Cyclization / 9: benzyloxycarbonylation / 10: benzylation / 11: desilylation;
DOI:10.1021/jo000186k

Reference yield:

: 287102-04-9
6-deoxy-3,4-O-isopropylidene-1-O-trityl-D-mannitol

: 287102-08-3
5-N-benzyloxycarbonyl-3,4-di-O-benzyl-2,5-imino-2,5,6-trideoxy-L-iditol

Guidance literature:: Multi-step reaction with 9 steps

1: 46 percent / Et₃N / CH₂Cl₂ / 10 h / 0 °C

2: NaN₃ / hexamethylphosphoric acid triamide / 8 h / 80 °C

3: TPAP; N-methylmorpholine N-oxide / CH₂Cl₂ / 1 h / 20 °C

4: 2.03 g / TFA(80percent) / 1 h / 0 °C

5: Et₃N; 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 12 h / 20 °C

6: 1.08 g / H₂ / rhodium-alumina / ethanol / 3 h

7: K₂CO₃ / tetrahydrofuran; H₂O / 0.5 h / 0 °C

8: NaH / dimethylformamide / 10 h / 20 °C

9: 628 mg / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 0 °C

With dmap; sodium azide; tetrapropylammonium perruthennate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; rhodium on alumina; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 1: mesylation / 2: Substitution / 3: Oxidation / 4: Ring cleavage / 5: silylation / 6: Cyclization / 7: benzyloxycarbonylation / 8: benzylation / 9: desilylation;
DOI:10.1021/jo000186k