(2S)-2-[(3R,5S)-3,5-dihydroxy-1-adamantyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid

Base Information

Chemical Name:(2S)-2-[(3R,5S)-3,5-dihydroxy-1-adamantyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid
CAS No.:681282-72-4
Molecular Formula:C₁₇H₂₇NO₆
Molecular Weight:341.404
Hs Code.:
DSSTox Substance ID:DTXSID90466333
Wikidata:Q82292873

Synonyms:(2S)-2-[(3R,5S)-3,5-dihydroxy-1-adamantyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid;681282-72-4;TRI048;DTXSID90466333

Suppliers and Price of (2S)-2-[(3R,5S)-3,5-dihydroxy-1-adamantyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic 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

TRC
Boc-3,5-dihydroxy-1-adamantyl-L-glycine
25mg
$ 165.00

Total 7 raw suppliers

Chemical Property of (2S)-2-[(3R,5S)-3,5-dihydroxy-1-adamantyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid

Chemical Property:

Boiling Point:534.7±35.0 °C(Predicted)
Density:1.406±0.06 g/cm3(Predicted)
XLogP3:0.8
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:5
Exact Mass:341.18383758
Heavy Atom Count:24
Complexity:550

Purity/Quality:

> 95% ^*data from raw suppliers

Boc-3,5-dihydroxy-1-adamantyl-L-glycine ^*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)O)C12CC3CC(C1)(CC(C3)(C2)O)O
Isomeric SMILES:CC(C)(C)OC(=O)N[C@H](C(=O)O)C12CC3C[C@](C1)(C[C@@](C3)(C2)O)O
Uses Boc-3,5-dihydroxy-1-adamantyl-L-glycine is a reactant in the synthesis of Saxagliptin (S143500), 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 (2S)-2-[(3R,5S)-3,5-dihydroxy-1-adamantyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid

There total 9 articles about (2S)-2-[(3R,5S)-3,5-dihydroxy-1-adamantyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic 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: 51.0%

: 361441-97-6
(alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.1^3,7]decane-1-acetic acid

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.1^3,7]decane-1-acetic acid

: 681282-72-4
(S)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dihydroxyadamantan-1-yl)acetic acid

Guidance literature:: With potassium hydroxide; potassium permanganate; at 60 - 90 ℃; for 1.5h;
DOI:10.1021/jm050261p

Reference yield: 25.0%

: 361442-00-4
(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.1^3,7]decane-1-acetic acid

: 681282-72-4
(S)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dihydroxyadamantan-1-yl)acetic acid

Guidance literature:: With potassium permanganate; potassium hydroxide; In water; at 60 - 85 ℃; for 1.5h;
DOI:10.1002/jlcr.3179

Reference yield:

: 361441-95-4
(S)-2-(adamantan-1-yl)-2-(((R)-2-hydroxy-1-phenylethyl)amino)acetonitrile

: 681282-72-4
(S)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dihydroxyadamantan-1-yl)acetic acid

Guidance literature:: Multi-step reaction with 4 steps

1: 78 percent / aq. HCl; AcOH / 18 h / 80 °C

2: H₂; AcOH / Pd(OH)2/C / methanol / 18 h / 2585.74 Torr

3: 4.07 g / K₂CO₃ / dimethylformamide / 19 h

4: 17 percent / KMnO₄; aq. KOH / 1.5 h / 60 - 90 °C

With hydrogenchloride; potassium hydroxide; potassium permanganate; hydrogen; potassium carbonate; acetic acid; palladium dihydroxide; In methanol; N,N-dimethyl-formamide;
DOI:10.1021/jm050261p