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

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Chemical Name:2,3,4-tri-O-benzyl-N-[(tert-butoxy)carbonyl]-5a-carba-2,5a-cyclo-β-D-glucopyranosylamine
CAS No.:452081-55-9
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-β-D-glucopyranosylamine

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

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

There total 11 articles about 2,3,4-tri-O-benzyl-N-[(tert-butoxy)carbonyl]-5a-carba-2,5a-cyclo-β-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: 93.0%

: 452081-54-8
6-O-acetyl-2,3,4-tri-O-benzyl-N-[(tert-butoxy)carbonyl]-5a-carba-2,5a-cyclo-β-D-glucopyranosylamine

: 452081-55-9
2,3,4-tri-O-benzyl-N-[(tert-butoxy)carbonyl]-5a-carba-2,5a-cyclo-β-D-glucopyranosylamine

Guidance literature:: With potassium carbonate; In methanol; at 20 ℃; for 0.75h;
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

: 452081-55-9
2,3,4-tri-O-benzyl-N-[(tert-butoxy)carbonyl]-5a-carba-2,5a-cyclo-β-D-glucopyranosylamine

Guidance literature:: Multi-step reaction with 11 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: 865 mg / KOH / ethanol; H₂O / 15 h / 100 °C

8.1: 963 mg / pyridine / 4 h / 20 °C

9.1: Et₃N; ethyl chloroformate / acetone / 1 h / 0 °C

9.2: 805 mg / NaN₃ / acetone; H₂O / 2.5 h / 0 - 23 °C

10.1: toluene / 1.5 h / 100 °C

10.2: 555 mg / toluene / 24 h / 100 °C

11.1: 93 percent / K₂CO₃ / methanol / 0.75 h / 20 °C

With pyridine; 1H-imidazole; potassium hydroxide; sodium tetrahydroborate; chloroformic acid ethyl ester; potassium carbonate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; nickel dichloride; copper; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 5.1: Cope elimination / 10.1: 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

: 452081-55-9
2,3,4-tri-O-benzyl-N-[(tert-butoxy)carbonyl]-5a-carba-2,5a-cyclo-β-D-glucopyranosylamine

Guidance literature:: Multi-step reaction with 9 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: 865 mg / KOH / ethanol; H₂O / 15 h / 100 °C

6.1: 963 mg / pyridine / 4 h / 20 °C

7.1: Et₃N; ethyl chloroformate / acetone / 1 h / 0 °C

7.2: 805 mg / NaN₃ / acetone; H₂O / 2.5 h / 0 - 23 °C

8.1: toluene / 1.5 h / 100 °C

8.2: 555 mg / toluene / 24 h / 100 °C

9.1: 93 percent / K₂CO₃ / methanol / 0.75 h / 20 °C

With pyridine; 1H-imidazole; potassium hydroxide; chloroformic acid ethyl ester; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; copper; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 3.1: Cope elimination / 8.1: Curtius degradation;
DOI:10.1002/1522-2675(200204)85:4<1118::AID-HLCA1118>3.0.CO;2-S