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

Base Information

• Chemical Name: 2,3,4-tri-O-benzyl-N-[(tert-butoxy)carbonyl]-6-O-[(tert-butyl)diphenylsilyl]-5a-carba-2,5a-cyclo-α-D-glucopyranosylamine
• CAS No.: 452081-58-2
• Molecular Formula: C₄₉H₅₇NO₆Si
• Molecular Weight: 784.08

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

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

There total 9 articles about 2,3,4-tri-O-benzyl-N-[(tert-butoxy)carbonyl]-6-O-[(tert-butyl)diphenylsilyl]-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:

(3aR)-4c,5t,6c-tris-benzyloxy-1-methyl-(3ar,6ac)-hexahydro-cyclopenta[c]isoxazole (73111-18-9) → 2,3,4-tri-O-benzyl-N-[(tert-butoxy)carbonyl]-6-O-[(tert-butyl)diphenylsilyl]-5a-carba-2,5a-cyclo-α-D-glucopyranosylamine (452081-58-2)

Guidance literature:

Multi-step reaction with 9 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

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; hydrazine hydrate; acetic acid; 3-chloro-benzenecarboperoxoic acid; nickel dichloride; sodium nitrite; copper; In 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:

1L-(1,2,4/3,5)-3,4,5-tri-O-benzyl-2-(dimethylamino)-1-(hydroxymethyl)cyclopentane-3,4,5-triol (73111-43-0) → 2,3,4-tri-O-benzyl-N-[(tert-butoxy)carbonyl]-6-O-[(tert-butyl)diphenylsilyl]-5a-carba-2,5a-cyclo-α-D-glucopyranosylamine (452081-58-2)

Guidance literature:

Multi-step reaction with 7 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

With 1H-imidazole; hydrogenchloride; hydrazine hydrate; 3-chloro-benzenecarboperoxoic acid; sodium nitrite; copper; In 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

Reference yield:

1L-(1,2,4/3,5)-3,4,5-tri-O-benzyl-2-(methylamino)-1-(hydroxymethyl)cyclopentane-3,4,5-triol → 2,3,4-tri-O-benzyl-N-[(tert-butoxy)carbonyl]-6-O-[(tert-butyl)diphenylsilyl]-5a-carba-2,5a-cyclo-α-D-glucopyranosylamine (452081-58-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: AcOH / CH₂Cl₂

1.2: 10.07 g / NaBH₃CN / CH₂Cl₂ / 4 h / 0 - 20 °C

2.1: 11.48 g / imidazole / dimethylformamide / 3 h / 20 °C

3.1: 83 percent / MCPBA / CH₂Cl₂ / 0.25 h / 0 - 20 °C

4.1: 63 percent / 0.25 h / 145 °C

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

6.1: 171 mg / NH₂NH₂*H₂O / ethanol / 6 h / 110 °C

7.1: 805 mg / HCl; NaNO₂ / dimethylformamide / 0.33 h / -10 °C

8.1: toluene / 1.5 h / 100 °C

8.2: 119 mg / toluene / 24 h / 100 °C

With 1H-imidazole; hydrogenchloride; hydrazine hydrate; acetic acid; 3-chloro-benzenecarboperoxoic acid; sodium nitrite; copper; In ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 4.1: Cope elimination / 8.1: Curtius degradation;

DOI:10.1002/1522-2675(200204)85:4<1118::AID-HLCA1118>3.0.CO;2-S

upstream raw materials:

tert-butyl alcohol

(1S,2S,3R,4R,5R,6S)-1,2,3-Tris-benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-bicyclo[3.1.0]hexane-6-carbonyl azide

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

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

Downstream raw materials:

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

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