(1R,2S,5S,3R,4R)-1-amino-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-amino-4-[(tert-butyldiphenylsilyloxy)methyl]-2,3-O-isopropylidene-2,3-dihydroxybicyclo[3.1.0]hexane
CAS No.:1069040-54-5
Molecular Formula:C₂₆H₃₅NO₃Si
Molecular Weight:437.654
Hs Code.:

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

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

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

Chemical Property:

Purity/Quality:: 97% ^*data from raw suppliers

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Technology Process of (1R,2S,5S,3R,4R)-1-amino-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-amino-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: 87.0%

: 1069040-52-3
(1R,2S,5S,3R,4R)-1-benzyloxycarbonylamino-4-[(tert-butyldiphenylsilyloxy)methyl]-2,3-O-isopropylidene-2,3-dihydroxybicyclo[3.1.0]hexane

: 1069040-54-5
(1R,2S,5S,3R,4R)-1-amino-4-[(tert-butyldiphenylsilyloxy)methyl]-2,3-O-isopropylidene-2,3-dihydroxybicyclo[3.1.0]hexane

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; for 2h; atmospheric pressure;
DOI:10.1021/jo801224j

Reference yield: 74.0%

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

: 1069040-54-5
(1R,2S,5S,3R,4R)-1-amino-4-[(tert-butyldiphenylsilyloxy)methyl]-2,3-O-isopropylidene-2,3-dihydroxybicyclo[3.1.0]hexane

Guidance literature:: (1R,2S,5S,3R,4R)-1-azidocarbonyl-4-[(tert-butyldiphenylsilyloxy)methyl]-2,3-O-isopropylidene-2,3-dihydroxybicyclo[3.1.0]hexane; In benzene; at 80 ℃; for 5h; Inert atmosphere;

With sodium hydroxide; In water; at 20 ℃; for 0.5h;
DOI:10.1021/acs.jmedchem.6b00689

Reference yield:

: 155792-02-2
ethyl (1R,4R)-8,8-dimethyl-5-oxo-7,9-dioxatricyclo[4.3.0.0^[2,4]]nonane-4-carboxylate

: 1069040-54-5
(1R,2S,5S,3R,4R)-1-amino-4-[(tert-butyldiphenylsilyloxy)methyl]-2,3-O-isopropylidene-2,3-dihydroxybicyclo[3.1.0]hexane

Guidance literature:: Multi-step reaction with 10 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

10.1: benzene / 5 h / 80 °C / Inert atmosphere

10.2: 0.5 h / 20 °C

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; benzene;
DOI:10.1021/acs.jmedchem.6b00689