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

Base Information

Chemical Name:(1R,2S,5S,3R,4R)-4-[(tert-butyldiphenylsilyloxy)methyl]-2,3-O-isopropylidene-2,3-dihydroxybicyclo[3.1.0]hexane-1-carboxylic acid
CAS No.:1069040-47-6
Molecular Formula:C₂₇H₃₄O₅Si
Molecular Weight:466.649
Hs Code.:

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

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

Supply Marketing:

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

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

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

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

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

There total 13 articles about (1R,2S,5S,3R,4R)-4-[(tert-butyldiphenylsilyloxy)methyl]-2,3-O-isopropylidene-2,3-dihydroxybicyclo[3.1.0]hexane-1-carboxylic acid 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: 76.0%

: 1069040-43-2
ethyl (2R,5R)-5-[[(tert-butyldiphenylsilyl)oxy]methyl]-8,8-dimethyl-7,9-dioxatricyclo[4.3.0.0^2,4]nonane-2-carboxylate

: 1069040-47-6
(1R,2S,5S,3R,4R)-4-[(tert-butyldiphenylsilyloxy)methyl]-2,3-O-isopropylidene-2,3-dihydroxybicyclo[3.1.0]hexane-1-carboxylic acid

Guidance literature:: With sodium hydroxide; In methanol; for 2h; Heating;
DOI:10.1021/jo801224j

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

: 1069040-47-6
(1R,2S,5S,3R,4R)-4-[(tert-butyldiphenylsilyloxy)methyl]-2,3-O-isopropylidene-2,3-dihydroxybicyclo[3.1.0]hexane-1-carboxylic acid

Guidance literature:: Multi-step reaction with 8 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

With pyridine; 1H-imidazole; sodium tetrahydroborate; palladium on activated charcoal; hydrogen; palladium(II) hydroxide; lithium hydride; triethylamine; trifluoroacetic acid; sodium hydroxide; In methanol; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;
DOI:10.1021/acs.jmedchem.6b00689

Reference yield:

: 155934-55-7
(4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde

: 1069040-47-6
(1R,2S,5S,3R,4R)-4-[(tert-butyldiphenylsilyloxy)methyl]-2,3-O-isopropylidene-2,3-dihydroxybicyclo[3.1.0]hexane-1-carboxylic acid

Guidance literature:: Multi-step reaction with 11 steps

1.1: tin(ll) chloride / dichloromethane / 3.5 h / 0 - 20 °C / Inert atmosphere; Large scale

2.1: 4-toluenesulfonyl azide; triethylamine / acetonitrile / 1 h / 0 - 20 °C / Inert atmosphere; Large scale

3.1: copper(l) iodide / toluene / 36 h / 80 - 83 °C / Inert atmosphere

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

5.1: trifluoroacetic acid / 40 h / Inert atmosphere

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

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

7.2: 0.5 h / 0 °C / Inert atmosphere

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

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

10.1: 1H-imidazole; triethylamine / N,N-dimethyl-formamide / 25 °C / Inert atmosphere

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

11.2: pH 4 - 5

With pyridine; 1H-imidazole; sodium tetrahydroborate; copper(l) iodide; 4-toluenesulfonyl azide; palladium on activated charcoal; hydrogen; palladium(II) hydroxide; lithium hydride; triethylamine; trifluoroacetic acid; tin(ll) chloride; sodium hydroxide; In methanol; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/acs.jmedchem.6b00689