M6633

α-D-Mannose pentaacetate

Name: α-<SC>D</SC>-Mannose pentaacetate
Brand: SIGMA
Price: 388 USD
Availability: InStock

Synonym(s):

1,2,3,4,6-Penta-O-acetyl-α-D-mannopyranose

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5 G

$388.00

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About This Item

Empirical Formula (Hill Notation):

C₁₆H₂₂O₁₁

CAS Number:

4163-65-9

Molecular Weight:

390.34

NACRES:

NA.25

PubChem Substance ID:

24897100

UNSPSC Code:

12352201

MDL number:

MFCD00069798

Key Documents

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InChI

1S/C16H22O11/c1-7(17)22-6-12-13(23-8(2)18)14(24-9(3)19)15(25-10(4)20)16(27-12)26-11(5)21/h12-16H,6H2,1-5H3

SMILES string

CC(=O)OCC1OC(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O

InChI key

LPTITAGPBXDDGR-UHFFFAOYSA-N

biological source

plant (ivory nut palm)

assay

≥98% (TLC)

form

powder

optical activity

[α]25/D 55.0 to 55.8°, c = 2.2% (w/v) in chloroform

technique(s)

thin layer chromatography (TLC): suitable

solubility

chloroform: 100 mg/mL, clear, colorless

storage temp.

−20°C

Quality Level

200

Related Categories

Biochemicals

Carbohydrates for Biochemical Research

Cell Culture Supplements & Reagents

Chemical Biology

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Show Differences

1 of 4

This Item	M1755	M2069	M1134
Sigma-Aldrich M6633 α-D-Mannose pentaacetate	Sigma-Aldrich M1755 α-D(+)Mannose 1-phosphate sodium salt hydrate	Sigma-Aldrich M2069 D-(+)-Mannose	Sigma-Aldrich M1134 L-(−)-Mannose
assay ≥98% (TLC)	assay ≥98% (TLC)	assay ≥99% (GC)	assay ≥99% (GC)
technique(s) thin layer chromatography (TLC): suitable	technique(s) thin layer chromatography (TLC): suitable	technique(s) gas chromatography (GC): suitable	technique(s) gas chromatography (GC): suitable
biological source plant (ivory nut palm)	biological source plant (Phytolacca fructus / pokeweed)	biological source wood	biological source -
Quality Level 200	Quality Level 200	Quality Level 200	Quality Level 100
solubility chloroform: 100 mg/mL, clear, colorless	solubility water: 50 mg/mL, clear, colorless	solubility water: 50 mg/mL, clear, colorless to faintly yellow	solubility water: 100 mg/mL, clear, colorless to very faintly yellow
form powder	form powder	form powder	form powder

General description

Mannose is a monosaccharide.

Application

α-D-Mannose pentaacetate was used for glycosylation in a study that assessed novel synthetic inhibitors of selectin-mediated cell adhesion. [1] It has also been used in a study to investigate stereospecific entry to spiroketal glycosides using alkylidenecarbene C−H insertion. [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.

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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Novel synthetic inhibitors of selectin-mediated cell adhesion: synthesis of 1,6-bis[3-(3-carboxymethylphenyl)-4-(2-alpha-D- mannopyranosyloxy)phenyl]hexane (TBC1269).

T P Kogan et al.

Journal of medicinal chemistry, 41(7), 1099-1111 (1998-04-17)

Reports of a high-affinity ligand for E-selectin, sialyl di-Lewis(x) (sLe(x)Le(x), 1), motivated us to incorporate modifications to previously reported biphenyl-based inhibitors that would provide additional interactions with the protein. These compounds were assayed for the ability to inhibit the binding

Stereospecific entry to [4.5]spiroketal glycosides using alkylidenecarbene C-H insertion.

Duncan J Wardrop et al.

Organic letters, 4(4), 489-492 (2002-02-15)

[reaction: see text] A novel method for the stereospecific preparation of [4.5]spiroketal glycosides utilizing the 1,5 C-H bond insertion of alkylidenecarbenes is described. Treatment of 2-oxopropyl beta-pyranosides A with lithium (trimethylsilyl)diazomethane in THF at -78 degrees C afforded 1,6-dioxaspiro[4,5]decenes B

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