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M5026

Sigma-Aldrich

Methyl 4-O-β-D-galactopyranosyl-β-D-glucopyranoside

Synonym(s):

β-D-Gal-[1→4]-β-D-Glc-1→OMe, Methyl β-lactoside

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About This Item

Empirical Formula (Hill Notation):
C13H24O11
CAS Number:
7216-69-5
Molecular Weight:
356.32
MDL number:
MFCD00079443
UNSPSC Code:
12352201
PubChem Substance ID:
24896968

form

solid

storage temp.

−20°C

SMILES string

[H][C@]1(O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)O[C@H]2[C@H](O)[C@@H](O)[C@H](OC)O[C@@H]2CO

InChI

1S/C13H24O11/c1-21-12-10(20)8(18)11(5(3-15)23-12)24-13-9(19)7(17)6(16)4(2-14)22-13/h4-20H,2-3H2,1H3/t4-,5-,6+,7+,8-,9-,10-,11-,12-,13+/m1/s1

InChI key

FHNIYFZSHCGBPP-ABBMIVAOSA-N

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
077F5026

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M A Ali et al.
Carbohydrate research, 216, 271-287 (1991-09-02)
Treatment of methyl beta-lactoside with triphenylphosphine-carbon tetrabromide in pyridine gave the 3',6'-anhydro-6-bromo-6-deoxy derivative, from which 6-thio derivatives were prepared, and methyl 3',4'-O-isopropylidene-beta-lactoside gave the 6,6'-dibromo-6,6'-dideoxy derivative. A dibromide was prepared also from methyl 4',6'-O-benzylidene-beta-lactoside by bromination with Ph3P-CBr4, acetylation, and
J L Asensio et al.
European journal of biochemistry, 233(2), 618-630 (1995-10-15)
The conformation in solution of methyl beta-galactopyranosyl-(1-->4)-alpha-glucopyranoside (methyl alpha-lactoside) and methyl beta-galactopyranosyl-(1-->6)-beta-glucopyranoside (methyl beta-allolactoside) has been studied through NMR spectroscopy and molecular mechanics calculations. NOE measurements both in the laboratory and rotating frames, have been interpreted in terms of an
P Fernandez et al.
Carbohydrate research, 271(1), 31-42 (1995-07-10)
Milk lactose is hydrolysed to D-galactose and D-glucose in the small intestine of mammals by the lactase-phlorizin hydrolase complex (LPH, EC 3.2.1.23-62). Lactase activity has broad substrate selectivity and several glycosides are substrates. Recently, using the monodeoxy derivatives of methyl
K Bock et al.
Carbohydrate research, 202, 131-149 (1990-07-15)
The 2'-,4'-, and 6'-deoxy derivatives of methyl beta-lactoside have been synthesised by deoxygenation at positions 2', 4', and 6', and the 3'-deoxy derivative was obtained by a glycosylation reaction. The 2'-O-methyl, 2'-O-benzyl, 2'-amino-2'-deoxy, and 1'-deuterio derivatives have been synthesized also.
Xiaosong Hu et al.
Acta crystallographica. Section C, Crystal structure communications, 66(Pt 2), o67-o70 (2010-02-04)
Methyl beta-D-galactopyranosyl-(1-->4)-alpha-D-mannopyranoside methanol 0.375-solvate, C(13)H(24)O(11).0.375CH(3)OH, (I), was crystallized from a methanol-ethanol solvent system in a glycosidic linkage conformation, with varphi' (O5(Gal)-C1(Gal)-O1(Gal)-C4(Man)) = -68.2 (3) degrees and psi' (C1(Gal)-O1(Gal)-C4(Man)-C5(Man)) = -123.9 (2) degrees , where the ring is defined by atoms
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