(1R,2S,5S,3R,4R)-1-azidocarbonyl-4-[(tert-butyldiphenylsilyloxy)methyl]-2,3-O-isopropylidene-2,3-dihydroxybicyclo[3.1.0]hexane

Base Information

• Chemical Name: (1R,2S,5S,3R,4R)-1-azidocarbonyl-4-[(tert-butyldiphenylsilyloxy)methyl]-2,3-O-isopropylidene-2,3-dihydroxybicyclo[3.1.0]hexane
• CAS No.: 1069040-48-7
• Molecular Formula: C₂₇H₃₃N₃O₄Si
• Molecular Weight: 491.662
• Mol file: 1069040-48-7.mol

Synonyms:(1R,2S,5S,3R,4R)-1-azidocarbonyl-4-[(tert-butyldiphenylsilyloxy)methyl]-2,3-O-isopropylidene-2,3-dihydroxybicyclo[3.1.0]hexane

Chemical Property of (1R,2S,5S,3R,4R)-1-azidocarbonyl-4-[(tert-butyldiphenylsilyloxy)methyl]-2,3-O-isopropylidene-2,3-dihydroxybicyclo[3.1.0]hexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,5S,3R,4R)-1-azidocarbonyl-4-[(tert-butyldiphenylsilyloxy)methyl]-2,3-O-isopropylidene-2,3-dihydroxybicyclo[3.1.0]hexane

There total 13 articles about (1R,2S,5S,3R,4R)-1-azidocarbonyl-4-[(tert-butyldiphenylsilyloxy)methyl]-2,3-O-isopropylidene-2,3-dihydroxybicyclo[3.1.0]hexane 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:

C39H43O8PSi → (1R,2S,5S,3R,4R)-1-azidocarbonyl-4-[(tert-butyldiphenylsilyloxy)methyl]-2,3-O-isopropylidene-2,3-dihydroxybicyclo[3.1.0]hexane (1069040-48-7)

Guidance literature:

With sodium azide; In water; acetone; for 0.5h;

DOI:10.1021/jo801224j

Reference yield:

ethyl (1R,4R)-8,8-dimethyl-5-oxo-7,9-dioxatricyclo[4.3.0.0^[2,4]]nonane-4-carboxylate (155792-02-2) → (1R,2S,5S,3R,4R)-1-azidocarbonyl-4-[(tert-butyldiphenylsilyloxy)methyl]-2,3-O-isopropylidene-2,3-dihydroxybicyclo[3.1.0]hexane (1069040-48-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: sodium tetrahydroborate / ethanol / 1 h / 0 - 15 °C / Inert atmosphere; Large scale

2.1: trifluoroacetic acid / 40 h / Inert atmosphere

3.1: pyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

4.1: lithium hydride / N,N-dimethyl-formamide / 6 h / 10 - 15 °C / Inert atmosphere

4.2: 0.5 h / 0 °C / Inert atmosphere

5.1: hydrogen; palladium on activated charcoal; palladium(II) hydroxide / methanol; water; acetic acid / 2 h / 25 °C

6.1: sodium tetrahydroborate / methanol / 0.5 h / 0 - 20 °C / Inert atmosphere

7.1: 1H-imidazole; triethylamine / N,N-dimethyl-formamide / 25 °C / Inert atmosphere

8.1: sodium hydroxide / methanol; water / 2 h / 80 °C / Inert atmosphere

8.2: pH 4 - 5

9.1: N-ethyl-N,N-diisopropylamine; chlorophosphoric acid diphenyl ester / acetone / 0.5 h / 20 °C / Inert atmosphere

9.2: 0.5 h / Inert atmosphere

With pyridine; 1H-imidazole; sodium tetrahydroborate; palladium on activated charcoal; hydrogen; palladium(II) hydroxide; lithium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; chlorophosphoric acid diphenyl ester; trifluoroacetic acid; sodium hydroxide; In methanol; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetone;

DOI:10.1021/acs.jmedchem.6b00689

Reference yield:

(1R,2S,4S,5S,3R)-1-ethoxycarbonyl-4-formyl-2,3-O-isopropylidene-2,3-dihydroxybicyclo[3.1.0]hexane (1069040-60-3) → (1R,2S,5S,3R,4R)-1-azidocarbonyl-4-[(tert-butyldiphenylsilyloxy)methyl]-2,3-O-isopropylidene-2,3-dihydroxybicyclo[3.1.0]hexane (1069040-48-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium tetrahydroborate / methanol / 0.5 h / 0 - 20 °C / Inert atmosphere

2.1: 1H-imidazole; triethylamine / N,N-dimethyl-formamide / 25 °C / Inert atmosphere

3.1: sodium hydroxide / methanol; water / 2 h / 80 °C / Inert atmosphere

3.2: pH 4 - 5

4.1: N-ethyl-N,N-diisopropylamine; chlorophosphoric acid diphenyl ester / acetone / 0.5 h / 20 °C / Inert atmosphere

4.2: 0.5 h / Inert atmosphere

With 1H-imidazole; sodium tetrahydroborate; triethylamine; N-ethyl-N,N-diisopropylamine; chlorophosphoric acid diphenyl ester; sodium hydroxide; In methanol; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/acs.jmedchem.6b00689

upstream raw materials:

(4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde

ethyl 3-(5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl)-3-oxopropanoate

ethyl 2-diazo-3-(5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl)-3-oxopropanoate

ethyl (1R,4R)-8,8-dimethyl-5-oxo-7,9-dioxatricyclo[4.3.0.0^[2,4]]nonane-4-carboxylate

Downstream raw materials:

(1R,2S,5S,3R,4R)-1-benzyloxycarbonylamino-4-[(tert-butyldiphenylsilyloxy)methyl]-2,3-O-isopropylidene-2,3-dihydroxybicyclo[3.1.0]hexane

(1R,2S,5S,3R,4R)-1-amino-4-[(tert-butyldiphenylsilyloxy)methyl]-2,3-O-isopropylidene-2,3-dihydroxybicyclo[3.1.0]hexane