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Merck
CN

943754

Tetra-O-acetyl-L-rhamnose

≥95%

Synonym(s):

1,2,3,4-Tetra-O-acetyl-L-rhamnopyranose, L-Mannopyranose, L-Rhamnopyranose tetraacetate, L-Mannopyranose, 6-deoxy-, tetraacetate, Mannopyranose, 6-deoxy-, tetraacetate, L-

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About This Item

Empirical Formula (Hill Notation):
C14H20O9
CAS Number:
30021-94-4
Molecular Weight:
332.30
MDL number:
MFCD30343562

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SMILES string

O=C(OC1OC(C)C(OC(=O)C)C(OC(=O)C)C1OC(=O)C)C

InChI key

QZQMGQQOGJIDKJ-IKOZNORXSA-N

InChI

1S/C14H20O9/c1-6-11(20-7(2)15)12(21-8(3)16)13(22-9(4)17)14(19-6)23-10(5)18/h6,11-14H,1-5H3/t6-,11-,12+,13+,14?/m0/s1

assay

≥95%

form

viscous liquid

reaction suitability

reaction type: Deprotonations

color

colorless to pale yellow

bp

129-130 °C (/ 0.1 Torr)

solubility

DMF: soluble, DMSO: soluble, soluble (DCM), soluble (EtOAc), soluble (MeOH)

density

±1.265-10 g/cm3 at 25 °C

storage temp.

2-8°C

Quality Level

100

General description

1,2,3,4-Tetra-O-acetyl-L-rhamnopyranose is the fully acetylated derivative of L-rhamnose (a 6-deoxy sugar). In this derivative, the hydroxyl groups at positions 1, 2, 3 and 4 are acetylated (protected as acetates). The molecule retains the methyl group at C-6 (hence “6-methyl”). This modification increases lipophilicity relative to the free sugar, and serves as a protected sugar moiety useful in glycosylation chemistry or as a building block in carbohydrate synthesis.

Application

  • Glycosylation Reactions: Used as a protected sugar donor or acceptor (once deprotected) in the synthesis of oligosaccharides or glycosylated natural products.
  • Carbohydrate chemistry & Medicinal Chemistry: For constructing analogues of sugar derivatives, or for attaching sugars to lipids, peptides, or drug molecules.
  • Material Science & Glyco-conjugation: As a sugar motif in modifying surfaces or polymers.
  • Organic Synthesis Teaching / Reference Compound: Helpful in illustrating protection/deprotection strategies with sugars.

Features and Benefits

  • Protected sugar hydroxyls: The acetyl protection stabilizes the sugar ring, prevents unwanted reactions at hydroxyl groups, and allows selective deprotection downstream.
  • Enhanced lipophilicity: Because of acetyl groups, more soluble in non-polar or moderately polar organic solvents, facilitating its use in non-aqueous glycosylation or as donor material.
  • Multiple reactive handles (protected): The acetates can be removed under defined conditions to liberate hydroxyls, enabling further functionalization.

Storage Class

10 - Combustible liquids

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000502550
0000502550

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