| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348262 | Tetrahedron: Asymmetry | 2007 | 8 Pages |
A short parallel synthesis of β-d-galactopyranosyl-O-pyridinoline (Gal-PYD), a collagen glycoconjugated cross-link, and of Gal-epiPYD, a (5S)-epimer, useful as internal standard in the analytical evaluation of the natural isomer in human tissue, is reported.
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tert-Butyl (2S,5R)-6-azido-2-benzyloxycarbonylamino-5-(3,4,6-tri-O-benzyl-2-O-acetyl-β-d-galactopyranosyloxy)hexanoateC47H56N4O11[α]D20=+9.3 (c 1, CH2Cl2)Source of chirality: l-glutamic acid and d-galactoseAbsolute configuration: (2S,5R)
tert-Butyl (2S,5R)-6-azido-2-N-benzyl-N-benzyloxycarbonylamino-5-(2,3,4,6-tetra-O-benzyl-β-d-galactopyranosyloxy)hexanoateC59H66IN4O10[α]D20=-2.4 (c 1, CH2Cl2)Source of chirality: l-glutamic acid and d-galactoseAbsolute configuration: (2S,5S)
tert-Butyl (2S,5S)-6-azido-2-N-benzyl-N-benzyloxycarbonylamino-5-(2,3,4,6-tetra-O-benzyl-β-d-galactopyranosyloxy)hexanoateC59H66IN4O10[α]D20=+7.0 (c 1, CH2Cl2)Source of chirality: l-glutamic acid and d-galactoseAbsolute configuration: (2S,5S)
tert-Butyl (2S,5R)-6-amino-2-benzyloxycarbonylamino-5-(3,4,6-tri-O-benzyl-2-O-acetyl-β-d-galactopyranosyloxy)hexanoateC47H58IN2O11[α]D20=+5.2 (c 1, CH2Cl2)Source of chirality: l-glutamic acid and d-galactoseAbsolute configuration: (2S,5R)
tert-Butyl (2S,5R)-6-amino-2-N-benzyl-N-benzyloxycarbonylamino-5-(2,3,4,6-tetra-O-benzyl-β-d-galactopyranosyloxy)hexanoateC59H68IN2O10[α]D20=-0.7 (c 1, CH2Cl2)Source of chirality: l-glutamic acid and d-galactoseAbsolute configuration: (2S,5R)
tert-Butyl (2S,5S)-6-amino-2-N-benzyl-N-benzyloxycarbonylamino-5-(2,3,4,6-tetra-O-benzyl-β-d-galactopyranosyloxy)hexanoateC59H68IN2O10[α]D20=+4.8 (c 1, CH2Cl2)Source of chirality: l-glutamic acid and d-galactoseAbsolute configuration: (2S,5S)
4-[(S)-2-tert-Butyloxycarbonylamino-2-tert-butyloxycarbonylethyl]-5-[(S)-3-tert-butyloxycarbonylamino-3-tert-butyloxycarbonylpropyl]-1-[(2R,5S)-5-N-benzyl-N-benzyloxycarbonylamino-5-tert-butyloxycarbonyl-2-(3,4,6-tri-O-benzyl-β-d-galactopyranosyloxy)pentyl]-3-pyridiniumolateC89H114IN4O19[α]D20=-0.7 (c 1, CH2Cl2)Source of chirality: l-glutamic acid and d-galactoseAbsolute configuration: (2′S,3″S,2‴R,5‴S)
4-[(S)-2-tert-Butyloxycarbonylamino-2-tert-butyloxycarbonylethyl]-5-[(S)-3-tert-butyloxycarbonylamino-3-tert-butyloxycarbonylpropyl]-1-[(2S,5S)-5-N-benzyl-N-benzyloxycarbonylamino-5-tert-butyloxycarbonyl-2-(3,4,6-tri-O-benzyl-β-d-galactopyranosyloxy)pentyl]-3-pyridiniumolateC89H114IN4O19[α]D20=+12.2 (c 1, CH2Cl2)Source of chirality: l-glutamic acid and d-galactoseAbsolute configuration: (2′S,3″S,2‴S,5‴S)
4-[(S)-2-Amino-2-carboxyethyl]-5-[(S)-3amino-3-carboxypropyl]-1-[(2R,5S)-5-amino-5-carboxy-2-(β-d-galactopyranosyloxy)pentyl]-3-pyridiniumolateC24H38IN4O13[α]D20=-4.4 (c 0.5, H2O)Source of chirality: l-glutamic acid and d-galactoseAbsolute configuration: (2′S,3″S,2‴R,5‴S)
4-[(S)-2-Amino-2-carboxyethyl]-5-[(S)-3amino-3-carboxypropyl]-1-[(2S,5S)-5-amino-5-carboxy-2-(β-d-galactopyranosyloxy)pentyl]-3-pyridiniumolateC24H38IN4O13[α]D20=+3.8 (c 0.5, H2O)Source of chirality: l-glutamic acid and d-galactoseAbsolute configuration: (2′S,3″S,2‴S,5‴S)
