2,3,4-tri-O-benzyl-N-[(tert-butoxy)carbonyl]-5a-carba-2,5a-cyclo-α-D-glucopyranosylamine

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Chemical Name:2,3,4-tri-O-benzyl-N-[(tert-butoxy)carbonyl]-5a-carba-2,5a-cyclo-α-D-glucopyranosylamine
CAS No.:452081-59-3
Molecular Formula:C₃₃H₃₉NO₆
Molecular Weight:545.676
Hs Code.:

Synonyms:2,3,4-tri-O-benzyl-N-[(tert-butoxy)carbonyl]-5a-carba-2,5a-cyclo-α-D-glucopyranosylamine

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Chemical Property of 2,3,4-tri-O-benzyl-N-[(tert-butoxy)carbonyl]-5a-carba-2,5a-cyclo-α-D-glucopyranosylamine

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Technology Process of 2,3,4-tri-O-benzyl-N-[(tert-butoxy)carbonyl]-5a-carba-2,5a-cyclo-α-D-glucopyranosylamine

There total 10 articles about 2,3,4-tri-O-benzyl-N-[(tert-butoxy)carbonyl]-5a-carba-2,5a-cyclo-α-D-glucopyranosylamine 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%

: 452081-58-2
2,3,4-tri-O-benzyl-N-[(tert-butoxy)carbonyl]-6-O-[(tert-butyl)diphenylsilyl]-5a-carba-2,5a-cyclo-α-D-glucopyranosylamine

: 452081-59-3
2,3,4-tri-O-benzyl-N-[(tert-butoxy)carbonyl]-5a-carba-2,5a-cyclo-α-D-glucopyranosylamine

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1.5h;
DOI:10.1002/1522-2675(200204)85:4<1118::AID-HLCA1118>3.0.CO;2-S

Reference yield:

: 73111-18-9
(3aR)-4c,5t,6c-tris-benzyloxy-1-methyl-(3ar,6ac)-hexahydro-cyclopenta[c]isoxazole

: 452081-59-3
2,3,4-tri-O-benzyl-N-[(tert-butoxy)carbonyl]-5a-carba-2,5a-cyclo-α-D-glucopyranosylamine

Guidance literature:: Multi-step reaction with 10 steps

1.1: 9.47 g / NaBH₄; NiCl₂ / methanol / 5 h / 20 °C

2.1: AcOH / CH₂Cl₂

2.2: 10.07 g / NaBH₃CN / CH₂Cl₂ / 4 h / 0 - 20 °C

3.1: 11.48 g / imidazole / dimethylformamide / 3 h / 20 °C

4.1: 83 percent / MCPBA / CH₂Cl₂ / 0.25 h / 0 - 20 °C

5.1: 63 percent / 0.25 h / 145 °C

6.1: Cu powder / toluene / 10 h / 110 °C

7.1: 171 mg / NH₂NH₂*H₂O / ethanol / 6 h / 110 °C

8.1: 805 mg / HCl; NaNO₂ / dimethylformamide / 0.33 h / -10 °C

9.1: toluene / 1.5 h / 100 °C

9.2: 119 mg / toluene / 24 h / 100 °C

10.1: 94 percent / Bu₄NF*3H₂O / tetrahydrofuran / 1.5 h / 20 °C

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; tetrabutyl ammonium fluoride; hydrazine hydrate; acetic acid; 3-chloro-benzenecarboperoxoic acid; nickel dichloride; sodium nitrite; copper; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 5.1: Cope elimination / 9.1: Curtius degradation;
DOI:10.1002/1522-2675(200204)85:4<1118::AID-HLCA1118>3.0.CO;2-S

Reference yield:

: 73111-43-0
1L-(1,2,4/3,5)-3,4,5-tri-O-benzyl-2-(dimethylamino)-1-(hydroxymethyl)cyclopentane-3,4,5-triol

: 452081-59-3
2,3,4-tri-O-benzyl-N-[(tert-butoxy)carbonyl]-5a-carba-2,5a-cyclo-α-D-glucopyranosylamine

Guidance literature:: Multi-step reaction with 8 steps

1.1: 11.48 g / imidazole / dimethylformamide / 3 h / 20 °C

2.1: 83 percent / MCPBA / CH₂Cl₂ / 0.25 h / 0 - 20 °C

3.1: 63 percent / 0.25 h / 145 °C

4.1: Cu powder / toluene / 10 h / 110 °C

5.1: 171 mg / NH₂NH₂*H₂O / ethanol / 6 h / 110 °C

6.1: 805 mg / HCl; NaNO₂ / dimethylformamide / 0.33 h / -10 °C

7.1: toluene / 1.5 h / 100 °C

7.2: 119 mg / toluene / 24 h / 100 °C

8.1: 94 percent / Bu₄NF*3H₂O / tetrahydrofuran / 1.5 h / 20 °C

With 1H-imidazole; hydrogenchloride; tetrabutyl ammonium fluoride; hydrazine hydrate; 3-chloro-benzenecarboperoxoic acid; sodium nitrite; copper; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 3.1: Cope elimination / 7.1: Curtius degradation;
DOI:10.1002/1522-2675(200204)85:4<1118::AID-HLCA1118>3.0.CO;2-S