ChemicalBook CAS DataBase List ACETOBROMO-ALPHA-D-GLUCURONIC ACID METHYL ESTER

ACETOBROMO-ALPHA-D-GLUCURONIC ACID METHYL ESTER synthesis

10synthesis methods

Product Name:ACETOBROMO-ALPHA-D-GLUCURONIC ACID METHYL ESTER
CAS Number:21085-72-3
Molecular formula:C13H17BrO9
Molecular Weight:397.17

Acetobromo-a-D-glucuronic acid methyl ester can be used as organic synthesis intermediate and pharmaceutical intermediate, mainly in laboratory research and development. It was prepared by acetylation and bromination of D-glucuronic acid methyl ester.

METHYL 1,2,3,4-TETRA-O-ACETYL-BETA-D-GLUCURONATE

7355-18-2
230 suppliers
$6.00/1g

ACETOBROMO-ALPHA-D-GLUCURONIC ACID METHYL ESTER

21085-72-3
224 suppliers
$11.00/1g

Yield:21085-72-3 96.98%

Reaction Conditions:

with hydrogen bromide;acetic acid at 0 - 20; for 2 h;

Steps:

3-O-acetyl-α-D-bromo-glucuronic acid methyl ester (9)
Compound 8 (5 g, 0.0133 mol) was slowly added to 33 % acetic acid solution of hydrogen bromide (20 mL) at 0 °C. The mixture was stirred at room temperature for 2 h. Benzene (50 mL) was added to the mixture, and the resulting mixture was concentrated under reduced pressure to syrup. The syrup was dissolved with ethyl acetate (100 mL). Then the mixture was washed with saturated sodium bicarbonate, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford 9 (5.12 g, 96.98%). mp 102.5~103.8 °C; ESI-MS (m/z): Cacld for {[C₁₃H₁₈BrO₉]⁺} 397.0134/399.0114, found 396.9410/398.9388. ¹H NMR(300 MHz, CDCl₃) δ: 5.79, 5.77 (1H, d, -CH), 5.34~5.13 (3H, m, 4×-CH), 4.21, 4.18 (1H, d, -CH), 3.75 (3H, s, -OCH₃), 2.05~2.04 (9H, m, 3×-COCH₃); ¹³C NMR (75 MHz, CDCl₃) δ: 169.80, 169.03, 168.45, 167.88 (4×-COCH₃), 89.16 (-CH), 72.95, 71.42, 70.22, 69.89 (4×-CH), 52.79 (-OCH₃), 20.45, 20.41, 20.38 (3×-COCH₃).

References:

Zhu, Hao-Hao;Chen, Yu-Qing;Cheng, Dong;Li, Wei;Wang, Tian-Lin;Wen, Hong-Mei;Chen, Long;Liu, Jian [Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,# 3,p. 882 - 884] Location in patent:supporting information

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