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Methyl β-D-xylopyranoside

Name: Methyl β-<SC>D</SC>-xylopyranoside
Brand: SIGMA

≥99% (GC)

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About This Item

Empirical Formula (Hill Notation):

C₆H₁₂O₅

CAS Number:

612-05-5

Molecular Weight:

164.16

NACRES:

NA.25

PubChem Substance ID:

24897051

UNSPSC Code:

12352201

EC Number:

210-289-7

MDL number:

MFCD00047532

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Properties

biological source

synthetic (organic)

Quality Level

200

assay

≥99% (GC)

form

powder

optical activity

[α]20/D -66.5 to -63.5, c = 1% (w/v) in water

technique(s)

gas chromatography (GC): suitable

color

white to off-white

mp

155-158 °C (lit.)

solubility

water: 100 mg/mL, clear to hazy, colorless to light yellow

storage temp.

room temp

SMILES string

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

InChI

1S/C6H12O5/c1-10-6-5(9)4(8)3(7)2-11-6/h3-9H,2H2,1H3/t3-,4+,5-,6-/m1/s1

InChI key

ZBDGHWFPLXXWRD-JGWLITMVSA-N

Description

Application

Methyl β-D-xylopyranoside has been used in a study to assess tetraisopropyldisiloxane-1,3-diyl as a versatile protecting group for pentopyranosides. [1] It has also been used in a study that investigated transacetylations to carbohydrates catalyzed by acetylxylan esterase in the presence of an organic solvent. [2]

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

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This Item	M9376	X3877	M0285
Sigma-Aldrich M5878 Methyl β-D-xylopyranoside	Sigma-Aldrich M9376 Methyl α-D-glucopyranoside	Sigma-Aldrich X3877 D-(+)-Xylose	Sigma-Aldrich M0285 Methyl-β-D-galactopyranoside
technique(s) gas chromatography (GC): suitable	technique(s) gas chromatography (GC): suitable	technique(s) gas chromatography (GC): suitable	technique(s) gas chromatography (GC): suitable
assay ≥99% (GC)	assay ≥99% (GC)	assay ≥99% (GC)	assay ≥98% (GC)
biological source synthetic (organic)	biological source synthetic (organic)	biological source -	biological source synthetic
solubility water: 100 mg/mL, clear to hazy, colorless to light yellow	solubility water: 50 mg/mL, clear, colorless	solubility H₂O: 1 M, clear, colorless	solubility water: 50 mg/mL, clear, colorless
Quality Level 200	Quality Level 200	Quality Level 200	Quality Level 200
form powder	form solid	form powder	form powder

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Deoxy and deoxyfluoro analogues of acetylated methyl beta-D-xylopyranoside--substrates for acetylxylan esterases.

Mária Mastihubová et al.

Carbohydrate research, 339(12), 2101-2110 (2004-07-29)

Four modified substrates for acetylxylan esterases, 2-deoxy, 3-deoxy, 2-deoxy-2-fluoro, and 3-deoxy-3-fluoro derivatives of di-O-acetylated methyl beta-D-xylopyranoside were synthesized via 2,3-anhydropentopyranoside precursors. Methyl 2,3-anhydro-4-O-benzyl-beta-D-ribopyranoside was transformed into methyl 2,3-anhydro-4-O-benzyl-beta-D-lyxopyranoside in three steps. The epoxide ring opening of 2,3-anhydropentopyranosides was accomplished either

Mode of action of acetylxylan esterase from Streptomyces lividans: a study with deoxy and deoxy-fluoro analogues of acetylated methyl beta-D-xylopyranoside.

Peter Biely et al.

Biochimica et biophysica acta, 1622(2), 82-88 (2003-07-26)

Streptomyces lividans acetylxylan esterase removes the 2- or 3-O-acetyl groups from methyl 2,4-di-O-acetyl- and 3,4-di-O-acetyl beta-D-xylopyranoside. When the free hydroxyl group was replaced with a hydrogen or fluorine, the rate of deacetylation was markedly reduced, but regioselectivity was not affected.

An efficient chemoenzymatic route to methyl 4-O-benzyl-2,3-anhydro-beta-D-lyxopyranoside from methyl beta-D-xylopyranoside.

Mária Mastihubová et al.

Carbohydrate research, 339(2), 425-428 (2003-12-31)

Methyl 4-O-benzyl-2,3-anhydro-beta-D-lyxopyranoside, an intermediate for the preparation of methyl beta-D-xylopyranoside derivatives modified at C-2, was obtained in five steps in 58% yield. The synthetic sequence starts from methyl beta-D-xylopyranoside through two main steps involving regioselective enzymatic acetylation and deacetylation catalyzed

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Global Trade Item Number

SKU	GTIN
M5878-5G	04061834060420
M5878-25G	04061832392004
M5878-10G	04061834060413

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Methyl β-D-xylopyranoside

≥99% (GC)

Select a Size

About This Item

biological source

Quality Level

assay

form

optical activity

technique(s)

color

mp

solubility

storage temp.

SMILES string

InChI

InChI key

Application

Other Notes

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Storage Class

wgk

flash_point_f

flash_point_c

ppe

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