3,4-Di-O-acetyl-L-fucal
(Synonyms: 2,6-脱水-1,5-二脱氧-L-阿拉伯-己-5-烯糖二乙酸酯) 目录号 : GC46561
A glycal precursor
Cas No.:54621-94-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
3,4-Di-O-acetyl-L-fucal is a glycal precursor that has been used in the palladium-catalyzed stereoselective synthesis of glycosides.1 It has also been used as a precursor in the copper-catalyzed stereoselective synthesis of 2-deoxyglycosides.2
1.Pal, K.B., Lee, J., Das, M., et al.Palladium(II)-catalyzed stereoselective synthesis of C-glycosides from glycals with diaryliodonium saltsOrg. Biomol. Chem.18(12)2242-2251(2020) 2.Palo-Nieto, C., Sau, A., Jeanneret, R., et al.Copper reactivity can be tuned to catalyze the stereoselective synthesis of 2-deoxyglycosides from glycalsOrg. Lett.22(5)1991-1996(2020)
| Cas No. | 54621-94-2 | SDF | |
| 别名 | 2,6-脱水-1,5-二脱氧-L-阿拉伯-己-5-烯糖二乙酸酯 | ||
| Canonical SMILES | CC(O[C@@H]1[C@H](OC(C)=O)[C@H](C)OC=C1)=O | ||
| 分子式 | C10H14O5 | 分子量 | 214.2 |
| 溶解度 | DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 mg/ml | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 4.6685 mL | 23.3427 mL | 46.6853 mL |
| 5 mM | 0.9337 mL | 4.6685 mL | 9.3371 mL |
| 10 mM | 0.4669 mL | 2.3343 mL | 4.6685 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Iodoalkoxylation of 1,5-anhydro-2-deoxy-hex-1-enitols (glycals)
Carbohydr Res 1990 Sep 19;205:71-86.PMID:2276153DOI:10.1016/0008-6215(90)80129-q.
Exclusive trans-addition is observed in the iodoalkoxylation of the 6-membered cyclic enol ethers 3,4-di-O-acetyl-L-rhamnal (1), 3,4-Di-O-acetyl-L-fucal (2), and related glycal derivatives. The main products from 1 and from 3,4,6-tri-O-acetyl-D-glucal (3) thus had the alpha-manno configuration. Similarly, alpha-talo products were obtained from 2 in 87-93% yield. The product distribution is not affected by the electronegativity of the 5-substituent. It is concluded that steric factors in the glycal and the nucleophile affect only the step of trans-diaxial opening of the intermediate iodonium ion. Enhanced yields of the desired trans-diaxial products were observed in reactions of glycals having the lyxo configuration when the reactions were conducted in tetrahydrofuran or methanol.
Halogenated L-fucose and D-galactose analogues: synthesis and metabolic effects
J Med Chem 1980 Feb;23(2):143-9.PMID:7359528DOI:10.1021/jm00176a008.
Several new analogues of L-fucose modified in the 2 position and the 5-methyl group have been synthesized as potential plasma-membrane glycoconjugate inhibitors or modifiers, and their biological effects have been studied. 2-Chloro-, 2-bromo-, and 2-iodo-2-deoxy-L-fucose (9a, 9b, and 13, respectively) have been prepared by addition of the appropriate halogen to 3,4-Di-O-acetyl-L-fucal, followed by hydrolysis of the anomeric halogen and the acetyl groups. A series of four halogenated 5-methyl analogues of L-fucose (4, X = F, Cl, Br, and I) have been obtained starting from 1,2:3,4-di-O-isopropylidene-L-galactose. The synthesis of this latter compound has been improved. A corresponding series of 6-deoxy-6-halo-D-galactose analogues, which are enantiomers of the 5-(halomethyl)-L-fucose analogues, has also been synthesized. Analogues 4b, 4c, and 9b at 1 x 10(-3) M specifically inhibited the incorporation of L-[3H]fucose into macromolecular components of SW613 human mammary tumor cells. Analogue 13 inhibited the growth of L1210 murine leukemic cells with an IC50 of 6 x 10(5) M in culture. 6-Deoxy-6-fluoro-D-galactose and its enantiomer 4a were found to be effective inhibitors of D-[3H]galactose and L-[3H]fucose incorporation, respectively, into macromolecular components of human mammary tumor cells. The effectiveness of inhibition was reduced with an increase in size of the halogen atom. Analogue 4a and its enantiomer have been tritiated at C-1 and both were found to be activated to a nucleotide sugar, which was followed by incorporation into the macromolecular fraction of SW613 human mammary tumor cells in vitro.
Synthesis and antitumor activity of 2'-bromo- and 2'-chloro-3'-acetoxy-3'-deaminodaunorubicin analogs
Carbohydr Res 1985 Dec 1;144(2):305-15.PMID:4092209DOI:10.1016/s0008-6215(00)90678-5.
Bromination of 3,4-di-O-acetyl-L-rhamnal (7) and subsequent glycosidic coupling under Koenigs-Knorr conditions with daunomycinone gave a mixture of three compounds having the beta-L-gluco (10), alpha-L-gluco (11), and alpha-L-manno (12) configurations. Analogous bromination of 3,4-Di-O-acetyl-L-fucal (13) followed by coupling with daunomycinone gave a mixture of three glycosides having the beta-L-galacto (16), alpha-L-galacto (17), and alpha-L-talo (18) configurations. Chlorination of 7 and coupling with daunomycinone in the presence of silver triflate gave products having the alpha-L-gluco (21) and alpha-L-manno (22) configurations, whereas 13, under similar conditions, gave only one stereoisomeric product, that having the alpha-L-galacto (24) configuration. Compounds 12 and 22 showed high in vivo activity in the P-388 lymphocytic leukemia assay.