(2S)-2-amino-2-[(2R,3S,4R,5R)-3,4-dihydroxy-5-[5-(hydroxymethyl)-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]acetic acid

Base Information

Chemical Name:(2S)-2-amino-2-[(2R,3S,4R,5R)-3,4-dihydroxy-5-[5-(hydroxymethyl)-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]acetic acid
CAS No.:21027-33-8
Deprecated CAS:11043-74-6
Molecular Formula:C11H15N3O8
Molecular Weight:317.255
Hs Code.:
UNII:C3QC06JMRJ
DSSTox Substance ID:DTXSID60943323
Nikkaji Number:J16.339B
Wikidata:Q27275152
Metabolomics Workbench ID:114890
Mol file:21027-33-8.mol

Synonyms:polyoxin C

Suppliers and Price of (2S)-2-amino-2-[(2R,3S,4R,5R)-3,4-dihydroxy-5-[5-(hydroxymethyl)-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]acetic acid

Supply Marketing:

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

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Total 1 raw suppliers

Chemical Property of (2S)-2-amino-2-[(2R,3S,4R,5R)-3,4-dihydroxy-5-[5-(hydroxymethyl)-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]acetic acid

Chemical Property:

Boiling Point:°Cat760mmHg
Flash Point:°C
PSA：188.10000
Density:1.785g/cm³
LogP:-3.23970
XLogP3:-5.5
Hydrogen Bond Donor Count:6
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:4
Exact Mass:317.08591445
Heavy Atom Count:22
Complexity:535

Purity/Quality:: >98% ^*data from raw suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:C1=C(C(=O)NC(=O)N1C2C(C(C(O2)C(C(=O)O)N)O)O)CO
Isomeric SMILES:C1=C(C(=O)NC(=O)N1[C@H]2[C@@H]([C@@H]([C@H](O2)[C@@H](C(=O)O)N)O)O)CO

Technology Process of (2S)-2-amino-2-[(2R,3S,4R,5R)-3,4-dihydroxy-5-[5-(hydroxymethyl)-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]acetic acid

There total 19 articles about (2S)-2-amino-2-[(2R,3S,4R,5R)-3,4-dihydroxy-5-[5-(hydroxymethyl)-2,4-dioxopyrimidin-1-yl]oxolan-2-yl]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:

: (S)-Benzyloxycarbonylamino-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(5-hydroxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-acetic acid

: 21027-33-8
1-(5'-amino-5'-deoxy-β-D-allofuranosyluronic acid)-5-hydroxymethyluracil

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃;

Reference yield:

: 127646-37-1
5-hydroxymethyl-1-(methyl 2',3'-di-O-acetyl-5'-azido-5'-deoxy-β-D-allofuranosyluronate)uracil

: 21027-33-8
1-(5'-amino-5'-deoxy-β-D-allofuranosyluronic acid)-5-hydroxymethyluracil

Guidance literature:: With barium dihydroxide; water; triphenylphosphine; Yield given. Multistep reaction; 1) THF, 25 deg C, 12 h, 2) dioxane, 25 deg C, 3 h;
DOI:10.1021/jo00299a030

Reference yield:

: 155154-68-0
methyl (5-azido-5-deoxy-1,2,3-tri-O-acetyl-D-allofuranosid)uronate

: 21027-33-8
1-(5'-amino-5'-deoxy-β-D-allofuranosyluronic acid)-5-hydroxymethyluracil

Guidance literature:: Multi-step reaction with 5 steps

1: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 1 h / Heating

2: H₂ / Pd-C / methanol / 20 °C

3: NaHCO₃ / toluene; dioxane / 1 h / 20 °C

4: LiOH*H₂O / tetrahydrofuran; H₂O / 4.5 h / 0 °C

5: H₂ / Pd-C / methanol / 20 °C

With lithium hydroxide; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium hydrogencarbonate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; water; toluene; acetonitrile;