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M6633

Sigma-Aldrich

α-D-Mannose pentaacetate

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C16H22O11
CAS Number:
4163-65-9
Molecular Weight:
390.34
MDL number:
MFCD00069798
UNSPSC Code:
12352201
PubChem Substance ID:
24897100
NACRES:
NA.25

biological source

plant (ivory nut palm)

Quality Level

200

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

SMILES string

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

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

InChI key

LPTITAGPBXDDGR-UHFFFAOYSA-N

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. It has also been used in a study to investigate stereospecific entry to spiroketal glycosides using alkylidenecarbene C−H insertion.

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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

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