2,3,4,6-Tetra-O-acetyl-alpha-D-galactopyranosyl bromide Chemical Properties

Melting point:

83-85 °C

alpha 

210 º (c=3, CHCl3)

Boiling point:

412.0±45.0 °C(Predicted)

Density 

1.7028 (rough estimate)

refractive index 

1.4490 (estimate)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly), Water (Slightly)

form 

Solid

color 

White to Pale Yellow

biological source

synthetic (organic)

optical activity

[α]25/D 200 to 225 °, c =0.5% (w/v) in chloroform

Water Solubility 

Sparingly soluble

BRN 

96671

Stability:

Temperature Sensitive; Store in freezer; Stabilized with 2% CaCO3

InChI

1S/C14H19BrO9/c1-6(16)20-5-10-11(21-7(2)17)12(22-8(3)18)13(14(15)24-10)23-9(4)19/h10-14H,5H2,1-4H3/t10-,11+,12+,13-,14+/m1/s1

InChIKey

CYAYKKUWALRRPA-HTOAHKCRSA-N

SMILES

CC(=O)OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H]1OC(C)=O

CAS DataBase Reference

3068-32-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

F 

8-10-21

HS Code 

29329990

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

2,3,4,6-Tetra-O-acetyl-alpha-D-galactopyranosyl bromide Usage And Synthesis

Chemical Properties

White Crystalline Solid

Uses

Temperature and moisture sensitive; Store in freezer; Stabilized with 2% CaCO3

Synthesis

2,3,4,6-Tetra-O-acetyl-alpha-D-galactopyranosyl bromide can be synthesized by that: Methanolysis of the adduct prepared from the reaction of tetra‐O‐acetyl‐α‐d‐glucopyranosyl bromide with N,N‐dimethylthioformamide afforded the corresponding tetra‐O‐acetyl‐1‐thio‐d‐glucopyranose with an anomer ratio α/β of 52:48 in 98% yield.

Purification Methods

Purify acetobromo-D-galactose as for the glucose analogue (next entry). If the compound melts lower than 87o or is highly coloured, then dissolve it in CHCl3 (ca 3 volumes) and extract with H2O (2 volumes), 5% aqueous NaHCO3, and again with H2O and dry it over Na2SO4. Filter and evaporate it in a vacuum. The partially crystalline solid or syrup is dissolved in dry Et2O (must be very dry) and recrystallised by adding pet ether (b 40-60o) to give a white product. [McKellan & Horecker Biochemical Preparations 11 111 1960, Beilstein 17/6 V 369.]

References

[1] TAKAYOSHI FUJIHIRA. Synthesis of Tetra-O-acetyl-1-thio-α-D-glucopyranose by Reaction of Tetra-O-acetyl-α-D-glucopyranosyl Bromide with N,N-Dimethylthioformamide.[J]. ChemInform, 2003, 34 33. DOI:10.1002/chin.200333198.

2,3,4,6-Tetra-O-acetyl-alpha-D-galactopyranosyl bromide(3068-32-4)Related Product Information

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