tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl]carbaMate

Base Information

• Chemical Name: tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl]carbaMate
• CAS No.: 1172623-99-2
• Molecular Formula: C16H21F2NO4
• Molecular Weight: 329.344
• Mol file: 1172623-99-2.mol

Synonyms:tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl]carbaMate;Omarigliptin Intermediate;D-glycero-Pentitol, 1,5-anhydro-3,4-dideoxy-5-C-(2,5-difluorophenyl)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-, (2ξ,5R)-;(2xi,5R)-1,5-Anhydro-3,4-dideoxy-5-C-(2,5-difluorophenyl)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-D-glycero-pentitol

Chemical Property of tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl]carbaMate

Chemical Property:

• Boiling Point: 439.7±45.0 °C(Predicted)
• PKA: 11.31±0.60(Predicted)
• PSA: 67.79000
• Density: 1.26±0.1 g/cm3(Predicted)
• LogP: 3.07130
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C

Purity/Quality:

99%, ^*data from raw suppliers

tert-Butyl((2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl)carbamate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl]carbaMate

There total 23 articles about tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-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: 89.0%

tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-3,4-dihydro-2H-pyran-3-yl]carbamate (1172623-98-1) → tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl]carbamate (1172623-99-2)

Guidance literature:

tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-3,4-dihydro-2H-pyran-3-yl]carbamate; With dimethylsulfide borane complex; In tert-butyl methyl ether; at 0 - 5 ℃; Inert atmosphere;

With sodium peroxoborate tetrahydrate; sodium hydrogencarbonate; In tert-butyl methyl ether; water; at 15 - 25 ℃; Inert atmosphere;

DOI:10.1021/acs.oprd.5b00267

Reference yield: 86.0%

((2R)-2-(2,5-difluorophenyl)-3,4-dihydro-2H-pyran-3-yl)carbamate → tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl]carbamate (1172623-99-2)

Guidance literature:

With dimethylsulfide borane complex; In tert-butyl methyl ether; toluene; at -7 - 15 ℃; for 3h;

DOI:10.1021/ol502661g

Reference yield: 53.0%

tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-3,4-dihydro-2H-pyran-3-yl]carbamate → tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-5-hydroxytetrahydro-2H-pyran-3-yl]carbamate (1172623-99-2)

Guidance literature:

tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-3,4-dihydro-2H-pyran-3-yl]carbamate; With dimethylsulfide borane complex; In tert-butyl methyl ether; at -10 - -5 ℃;

With dihydrogen peroxide; sodium hydroxide; In tert-butyl methyl ether; water; at 0 - 26 ℃; for 14h;

upstream raw materials:

tert-butyl [(2R,3S)-2-(2,5-difluorophenyl)-3,4-dihydro-2H-pyran-3-yl]carbamate

(±)-tert-butyl (1-(methoxy(methyl)amino)-1-oxopent-4-yn-2-yl)carbamate

di-tert-butyl dicarbonate

(±)-tert-butyl (1-(2,5-difluorophenyl)-1-oxopent-4-yn-2-yl)carbamate

Downstream raw materials:

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

tert-butyl ((2R,3S,5S)-2-(2,5-difluorophenyl)-5-(pyrrolo[3,4-c]-pyrazol-5(1H,4H,6H)-yl)tetrahydro-2H-pyran-3-yl)carbamate

Omarigliptin

tert-butyl {(2R,3S,5R)-2-(2,5-difluorophenyl)-5-[2-(methylsulfonyl)-2,6-dihydropyrrolo[3,4-c]pyrazol-5(4H)-yl]tetrahydro-2H-pyran-3-yl}carbamate

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