Tert-butyl N-[(1S)-2-[(1S,3S,5S)-3-cyano-2-azabicyclo[3.1.0]hexan-2-yl]-1-[(5S,7R)-3-hydroxy-1-adamantyl]-2-oxoethyl]carbamate

Base Information

Chemical Name:Tert-butyl N-[(1S)-2-[(1S,3S,5S)-3-cyano-2-azabicyclo[3.1.0]hexan-2-yl]-1-[(5S,7R)-3-hydroxy-1-adamantyl]-2-oxoethyl]carbamate
CAS No.:709031-43-6
Molecular Formula:C23H33N3O4
Molecular Weight:415.533
Hs Code.:
European Community (EC) Number:687-691-8

Synonyms:Tert-butyl N-[(1S)-2-[(1S,3S,5S)-3-cyano-2-azabicyclo[3.1.0]hexan-2-yl]-1-[(5S,7R)-3-hydroxy-1-adamantyl]-2-oxoethyl]carbamate;709031-43-6;SCHEMBL15847121

Suppliers and Price of Tert-butyl N-[(1S)-2-[(1S,3S,5S)-3-cyano-2-azabicyclo[3.1.0]hexan-2-yl]-1-[(5S,7R)-3-hydroxy-1-adamantyl]-2-oxoethyl]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
Boc-Saxagliptin
10mg
$ 220.00

Total 35 raw suppliers

Chemical Property of Tert-butyl N-[(1S)-2-[(1S,3S,5S)-3-cyano-2-azabicyclo[3.1.0]hexan-2-yl]-1-[(5S,7R)-3-hydroxy-1-adamantyl]-2-oxoethyl]carbamate

Chemical Property:

Vapor Pressure:0mmHg at 25°C
Refractive Index:1.594
Boiling Point:624.716 °C at 760 mmHg
PKA:11.45±0.46(Predicted)
Flash Point:331.617 °C
PSA：106.15000
Density:1.292 g/cm³
LogP:2.86628
XLogP3:2.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:5
Exact Mass:415.24710654
Heavy Atom Count:30
Complexity:810

Purity/Quality:

99.9% ^*data from raw suppliers

Boc-Saxagliptin ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC(C)(C)OC(=O)NC(C(=O)N1C(CC2C1C2)C#N)C34CC5CC(C3)CC(C5)(C4)O
Isomeric SMILES:CC(C)(C)OC(=O)N[C@H](C(=O)N1[C@@H](C[C@H]2[C@@H]1C2)C#N)C34C[C@H]5C[C@@H](C3)CC(C5)(C4)O
Uses Boc-Saxagliptin is a Saxagliptin (S143500) impurity, a potent and selective reversible inhibitor of dipeptidyl peptidase-4, which is being developed for the treatment of type 2 diabetes. It is absorbed rapidly after oral administration and has a pharmacokinetic profile compatible with once daily dosing.

Technology Process of Tert-butyl N-[(1S)-2-[(1S,3S,5S)-3-cyano-2-azabicyclo[3.1.0]hexan-2-yl]-1-[(5S,7R)-3-hydroxy-1-adamantyl]-2-oxoethyl]carbamate

There total 54 articles about Tert-butyl N-[(1S)-2-[(1S,3S,5S)-3-cyano-2-azabicyclo[3.1.0]hexan-2-yl]-1-[(5S,7R)-3-hydroxy-1-adamantyl]-2-oxoethyl]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: 97.9%

: 866083-42-3
(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carbonitrile

: Na⁽¹⁺⁾*C₁₇H₂₆NO₅^(1-)

: 709031-43-6
3-cyano-(αS)-α-(3-hydroxytricyclo[3.3.1.1^3,7]dec-1-yl)-β-oxo-(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-2-ethanecarbamic acid 1,1-dimethylethyl ester

Guidance literature:: Na⁽¹⁺⁾*C₁₇H₂₆NO₅^(1-); With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; In ethyl acetate; acetonitrile; at 20 ℃; for 5h;

(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carbonitrile; In ethyl acetate; acetonitrile; at 20 ℃; for 2h; Reagent/catalyst;

Reference yield: 92.3%

: 361442-01-5
tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.1³'⁷]dec-1-yl)-2-oxoethyl]carbamate

: 709031-43-6
3-cyano-(αS)-α-(3-hydroxytricyclo[3.3.1.1^3,7]dec-1-yl)-β-oxo-(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-2-ethanecarbamic acid 1,1-dimethylethyl ester

Guidance literature:: tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.1³'⁷]dec-1-yl)-2-oxoethyl]carbamate; With pyridine; trifluoroacetic anhydride; In tetrahydrofuran; for 1h;

With potassium hydroxide; In methanol; at 20 ℃; for 18h;
DOI:10.1021/jm050261p