1-O-benzyl 2-O-methyl (2R,3S,4S)-3-[(2S)-2-hydroxy-2-[(2S)-oxiran-2-yl]ethyl]-4-prop-1-en-2-ylpyrrolidine-1,2-dicarboxylate

C21H27NO6 — CID 101133635

IUPAC1-O-benzyl 2-O-methyl (2R,3S,4S)-3-[(2S)-2-hydroxy-2-[(2S)-oxiran-2-yl]ethyl]-4-prop-1-en-2-ylpyrrolidine-1,2-dicarboxylate
SMILESC=C(C)[C@H]1CN(C(=O)OCc2ccccc2)[C@@H](C(=O)OC)[C@H]1C[C@H](O)[C@@H]1CO1
InChIInChI=1S/C21H27NO6/c1-13(2)16-10-22(21(25)28-11-14-7-5-4-6-8-14)19(20(24)26-3)15(16)9-17(23)18-12-27-18/h4-8,15-19,23H,1,9-12H2,2-3H3/t15-,16+,17-,18-,19+/m0/s1
InChIKeyXGUSFDCGDXYKFA-XCDZQEORSA-N
MW389.45 g/mol
LogP2.14
Rot. Bonds7

About 1-O-benzyl 2-O-methyl (2R,3S,4S)-3-[(2S)-2-hydroxy-2-[(2S)-oxiran-2-yl]ethyl]-4-prop-1-en-2-ylpyrrolidine-1,2-dicarboxylate

1-O-benzyl 2-O-methyl (2R,3S,4S)-3-[(2S)-2-hydroxy-2-[(2S)-oxiran-2-yl]ethyl]-4-prop-1-en-2-ylpyrrolidine-1,2-dicarboxylate (PubChem CID 101133635) has the molecular formula C21H27NO6 and a molecular weight of 389.45 g/mol. Its IUPAC name is 1-O-benzyl 2-O-methyl (2R,3S,4S)-3-[(2S)-2-hydroxy-2-[(2S)-oxiran-2-yl]ethyl]-4-prop-1-en-2-ylpyrrolidine-1,2-dicarboxylate.

Molecular Properties

Compound Name1-O-benzyl 2-O-methyl (2R,3S,4S)-3-[(2S)-2-hydroxy-2-[(2S)-oxiran-2-yl]ethyl]-4-prop-1-en-2-ylpyrrolidine-1,2-dicarboxylate
PubChem CID101133635
Molecular FormulaC21H27NO6
Molecular Weight389.45 g/mol
Exact Mass389.18
IUPAC Name1-O-benzyl 2-O-methyl (2R,3S,4S)-3-[(2S)-2-hydroxy-2-[(2S)-oxiran-2-yl]ethyl]-4-prop-1-en-2-ylpyrrolidine-1,2-dicarboxylate
SMILESC=C(C)[C@H]1CN(C(=O)OCc2ccccc2)[C@@H](C(=O)OC)[C@H]1C[C@H](O)[C@@H]1CO1
InChIInChI=1S/C21H27NO6/c1-13(2)16-10-22(21(25)28-11-14-7-5-4-6-8-14)19(20(24)26-3)15(16)9-17(23)18-12-27-18/h4-8,15-19,23H,1,9-12H2,2-3H3/t15-,16+,17-,18-,19+/m0/s1
InChIKeyXGUSFDCGDXYKFA-XCDZQEORSA-N
XLogP2.14
TPSA88.60 Ų
H-Bond Donors1
H-Bond Acceptors6
Rotatable Bonds7
Heavy Atoms28
Complexity—

Lipinski Rule of Five

Passes Rule of Five

RuleValue
MW ≤ 500389.45
LogP ≤ 52.14
H-Bond Donors ≤ 51
H-Bond Acceptors ≤ 106

Computed Properties (RDKit)

Structural Alerts{'alert_name': 'isolated_alkene', 'substructure': 'N/A'}, {'alert_name': 'Three-membered_heterocycle', 'substructure': 'N/A'}

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Related Compounds

Methyl (2S,5R)-1-cbz-5-hydroxy-6-methoxypipecolinate
CID 11771651
(2S,3R)-3-cyclohexyl-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid
CID 58051374
2-O-benzyl 1-O-tert-butyl (2R,4S)-4-[(4-fluorophenyl)methyl]-5-hydroxypyrrolidine-1,2-dicarboxylate
CID 176761458
2-O-benzyl 1-O-tert-butyl (2R,4R)-4-fluoro-4-[(4-fluorophenyl)methyl]-5-hydroxypyrrolidine-1,2-dicarboxylate
CID 176761612
1-O-benzyl 2-O-methyl (4R)-4-fluoro-2-[2-(oxiran-2-yl)ethyl]pyrrolidine-1,2-dicarboxylate
CID 176835304
1-O-benzyl 2-O-methyl (4R)-2-[2-(3-ethyloxiran-2-yl)ethyl]-4-fluoropyrrolidine-1,2-dicarboxylate
CID 177989635
2-O-benzyl 1-O-tert-butyl (4R)-2-(3,4-dihydroxy-4-methylpentyl)-4-fluoropyrrolidine-1,2-dicarboxylate
CID 177990588
2-O-benzyl 1-O-tert-butyl (4R)-4-fluoro-2-(4-hydroxy-4-methyl-3-methylsulfonyloxypentyl)pyrrolidine-1,2-dicarboxylate
CID 177990894
(2S,3S,4S)-3-(2-hydroxyethyl)-1-phenylmethoxycarbonyl-4-prop-1-en-2-ylpyrrolidine-2-carboxylic acid
CID 10936528
benzyl (4R)-4-[(2S,4R,5R)-4,5-dihydroxy-6-oxooxan-2-yl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
CID 11164423
1-O-benzyl 2-O-methyl (2S,3R,4R)-4-hydroxy-3-(2-hydroxyethyl)pyrrolidine-1,2-dicarboxylate
CID 11544331
1-O-benzyl 2-O-methyl (2S,5R,6S)-5-hydroxy-6-prop-2-enylpiperidine-1,2-dicarboxylate
CID 11660001

Frequently Asked Questions

What is the IUPAC name of 1-O-benzyl 2-O-methyl (2R,3S,4S)-3-[(2S)-2-hydroxy-2-[(2S)-oxiran-2-yl]ethyl]-4-prop-1-en-2-ylpyrrolidine-1,2-dicarboxylate?
The IUPAC name of 1-O-benzyl 2-O-methyl (2R,3S,4S)-3-[(2S)-2-hydroxy-2-[(2S)-oxiran-2-yl]ethyl]-4-prop-1-en-2-ylpyrrolidine-1,2-dicarboxylate (CID 101133635) is 1-O-benzyl 2-O-methyl (2R,3S,4S)-3-[(2S)-2-hydroxy-2-[(2S)-oxiran-2-yl]ethyl]-4-prop-1-en-2-ylpyrrolidine-1,2-dicarboxylate.
What is the SMILES notation for 1-O-benzyl 2-O-methyl (2R,3S,4S)-3-[(2S)-2-hydroxy-2-[(2S)-oxiran-2-yl]ethyl]-4-prop-1-en-2-ylpyrrolidine-1,2-dicarboxylate?
The canonical SMILES for 1-O-benzyl 2-O-methyl (2R,3S,4S)-3-[(2S)-2-hydroxy-2-[(2S)-oxiran-2-yl]ethyl]-4-prop-1-en-2-ylpyrrolidine-1,2-dicarboxylate is C=C(C)[C@H]1CN(C(=O)OCc2ccccc2)[C@@H](C(=O)OC)[C@H]1C[C@H](O)[C@@H]1CO1.
What is the InChIKey of 1-O-benzyl 2-O-methyl (2R,3S,4S)-3-[(2S)-2-hydroxy-2-[(2S)-oxiran-2-yl]ethyl]-4-prop-1-en-2-ylpyrrolidine-1,2-dicarboxylate?
The InChIKey is XGUSFDCGDXYKFA-XCDZQEORSA-N. The full InChI is InChI=1S/C21H27NO6/c1-13(2)16-10-22(21(25)28-11-14-7-5-4-6-8-14)19(20(24)26-3)15(16)9-17(23)18-12-27-18/h4-8,15-19,23H,1,9-12H2,2-3H3/t15-,16+,17-,18-,19+/m0/s1.
What are the key properties of 1-O-benzyl 2-O-methyl (2R,3S,4S)-3-[(2S)-2-hydroxy-2-[(2S)-oxiran-2-yl]ethyl]-4-prop-1-en-2-ylpyrrolidine-1,2-dicarboxylate?
1-O-benzyl 2-O-methyl (2R,3S,4S)-3-[(2S)-2-hydroxy-2-[(2S)-oxiran-2-yl]ethyl]-4-prop-1-en-2-ylpyrrolidine-1,2-dicarboxylate has a molecular weight of 389.45 g/mol, XLogP of 2.14, 7 rotatable bonds, 1 hydrogen bond donors, and 6 hydrogen bond acceptors.
Where does this data come from?
All data for 1-O-benzyl 2-O-methyl (2R,3S,4S)-3-[(2S)-2-hydroxy-2-[(2S)-oxiran-2-yl]ethyl]-4-prop-1-en-2-ylpyrrolidine-1,2-dicarboxylate is sourced from PubChem (CID 101133635), the world's largest open chemistry database maintained by the National Library of Medicine (NIH).