tert-butyl ((2S,3R)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate

Base Information

Chemical Name:tert-butyl ((2S,3R)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate
CAS No.:1456616-42-4
Molecular Formula:C16H19F2NO4
Molecular Weight:327.328
Hs Code.:
Mol file:1456616-42-4.mol

Synonyms:tert-butyl ((2S,3R)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate;N-[(2S,3R)-2-(2,5-Difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester

Suppliers and Price of tert-butyl ((2S,3R)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate

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

TRC
N-?[(2S,?3R)?-?2-?(2,?5-?Difluorophenyl)?tetrahydro-?5-?oxo-?2H-?pyran-?3-?yl]?carbamicAcid1,?1-?DimethylethylEster
25g
$ 1585.00

Total 6 raw suppliers

Chemical Property of tert-butyl ((2S,3R)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate

Chemical Property:

Boiling Point:433.4±45.0 °C(Predicted)
PKA:11.00±0.40(Predicted)
PSA：64.63000
Density:1.25±0.1 g/cm3(Predicted)
LogP:3.27950

Purity/Quality:

99% ^*data from raw suppliers

N-?[(2S,?3R)?-?2-?(2,?5-?Difluorophenyl)?tetrahydro-?5-?oxo-?2H-?pyran-?3-?yl]?carbamicAcid1,?1-?DimethylethylEster ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Uses N-?[(2S,?3R)?-?2-?(2,?5-?Difluorophenyl)?tetrahydro-?5-?oxo-?2H-?pyran-?3-?yl]?carbamic Acid 1,?1-?Dimethylethyl Ester is a analog of Omarigliptin (O633100), a potent and selective dipeptidyl peptidase 4 (DPP-4) inhibitor to be used as treatment for type 2 diabetes.

Technology Process of tert-butyl ((2S,3R)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate

There total 15 articles about tert-butyl ((2S,3R)-2-(2,5-difluorophenyl)-5-oxotetrahydro-2H-pyran-3-yl)carbamate 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: 47.7%

: tert-butyl [(2S,3R)-5-methylene-2-(2,5-difluorophenyl)-tetrahydro-2H-pyran-3-yl]carbamate

: 1456616-42-4
tert-butyl [(2S,3R)-5-oxo-2-(2,5-difluorophenyl)tetrahydro-2H-pyran-3-yl]carbamate

Guidance literature:: With sodium periodate; osmium(VIII) oxide; In 1,4-dioxane; water; at 0 ℃; for 2h;
DOI:10.1021/jm401992e

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 5-amino-6-(2,5-difluorophenyl)tetrahydro-2H-pyran-3-ol

: 951127-25-6
N-[(2R,3S)-2-(2,5-difluorophenyl)tetrahydro-5-oxo-2H-pyran-3-yl]carbamic acid 1,1-dimethylethyl ester

: 1456616-42-4
tert-butyl [(2S,3R)-5-oxo-2-(2,5-difluorophenyl)tetrahydro-2H-pyran-3-yl]carbamate

Guidance literature:: 5-amino-6-(2,5-difluorophenyl)tetrahydro-2H-pyran-3-ol; With D-Malic acid; In methanol; ethanol; for 4h; Reflux;

di-tert-butyl dicarbonate; With sodium hydroxide; In water; pH=8 - 9;

With ruthenium trichloride; sodium bromate; acetic acid; In water; acetonitrile; at 0 - 5 ℃; Overall yield = 6.7 g; Optical yield = 89.3 %ee;

Reference yield:

: 951127-28-9
6-(2,5-difluorophenyl)-3-methylidene-5-nitro-3,4-dihydro-2H-pyran

: 1456616-42-4
tert-butyl [(2S,3R)-5-oxo-2-(2,5-difluorophenyl)tetrahydro-2H-pyran-3-yl]carbamate

Guidance literature:: Multi-step reaction with 5 steps

1: sodium tetrahydroborate

2: Chiralpak 1A / ethanol; hexane / Resolution of racemate

3: zinc; hydrogenchloride / water

4: ChiralCel AD

5: rhodium(III) chloride; sodium periodate

With hydrogenchloride; sodium tetrahydroborate; sodium periodate; rhodium(III) chloride; zinc; In ethanol; hexane; water;
DOI:10.1016/j.bmcl.2013.07.061