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114861-22-2

114861-22-2

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114861-22-2 Usage

Uses

1,2-O-Isopropylidene-a-L-xylofuranose can be used as organic synthesis intermediates and pharmaceutical intermediates, mainly in laboratory research and development processes and chemical production processes.

Synthesis

((3aS,5R,6S,6aS)-6-Hydroxy-2,2-dimethyltetrahydrofuro[3,2-d][1,3]dioxol-5-yl)(morpholino)methanone (134). Step 1) (3aS,5S,6R,6aS)-5-(Hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,2-d][1,3]dioxol-6-ol. To a suspension of L-(-)-xylose (133, 19.15 g, 127.5 mmol) and MgSO4 (30.72 g, 255.0 mmol) in acetone (190 mL) was added conc. H2SO4 (1.9 mL) at room temperature. After 12 h, the reaction mixture (all L-(-)-xylose had been consumed) was filtered and the collected solids were washed with acetone (twice, 20 mL per wash). The stirring yellow filtrate was neutralized with NH4OH solution to pH ~ 9. The suspended solids were removed by filtration. The filtrate was concentrated to afford crude bis-acetonide intermediate as yellow oil. The yellow oil was suspended in water (5 mL), and then the pH was adjusted from 9 to 2 with 1 N HCl in water solution. The reaction mixture was stirred for 12 h at room temperature. The resulting mixture was neutralized by the addition of 25% (w/w) K3PO4 in water until pH ~ 7. The mixture was extracted with EtOAc. The organic layer was dried over MgSO4 filtered, and concentrated in vacuo. The crude product was purified by silica gel column chromatography. Yield: (12.63 g, 52%) as yellow oil. 1H NMR (400 MHz, CD3OD) δ 5.88 (d, J = 4.0 Hz, 1H), 4.47 (d, J 4.0 Hz, 1H), 4.18-4.14 (m, 1H), 4.1 1 (d, J = 2.8 Hz, 1H), 3.83-3.71 (m, 2H), 1.45 (s, 3H), 1.29 (s, 3H).

Check Digit Verification of cas no

The CAS Registry Mumber 114861-22-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,4,8,6 and 1 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 114861-22:
(8*1)+(7*1)+(6*4)+(5*8)+(4*6)+(3*1)+(2*2)+(1*2)=112
112 % 10 = 2
So 114861-22-2 is a valid CAS Registry Number.

114861-22-2Relevant articles and documents

Arabinose 5-phosphate analogues as mechanistic probes for Neisseria meningitidis 3-deoxy-d-manno-octulosonate 8-phosphate synthase

Ahn, Meekyung,Cochrane, Fiona C.,Patchett, Mark L.,Parker, Emily J.

, p. 9830 - 9836 (2008)

3-Deoxy-d-manno-octulosonate 8-phosphate (KDO8P) synthase catalyses the condensation reaction between phosphoenolpyruvate and d-arabinose 5-phosphate (d-A5P) in a key step in lipopolysaccharide biosynthesis in Gram-negative bacteria. The KDO8P synthase from Neisseria meningitidis was cloned into Escherichia coli, overexpressed and purified. A variety of d-A5P stereoisomers were tested as substrates, of these only d-A5P and l-X5P were substrates. The Asn59Ala mutant of N. meningitidis KDO8P synthase was constructed and this mutant retained less than 1% of the wild-type activity. These results are consistent with a catalytic mechanism for this enzyme in which the C2 and C3 hydroxyl groups of d-A5P and Asn59 are critical.

Process development of sotagliflozin, a dual inhibitor of sodium- Glucose cotransporter-1/2 for the treatment of diabetes

Zhao, Matthew M.,Zhang, Haiming,Iimura, Shinya,Bednarz, Mark S.,Song, Qiu-Ling,Lim, Ngiap-Kie,Yan, Jie,Wu, Wenxue,Dai, Kuangchu,Gu, Xiaodong,Wang, Youchu

, p. 2689 - 2701 (2020/11/03)

The development of an efficient manufacturing process for sotagliflozin (LX4211), a dual inhibitor of sodium- glucose cotransporter-1/2 (SGLT-1/2) for the treatment of diabetes, is described. Sotagliflozin features five contiguous chiral centers on the carbohydrate core flanked by a thioether group and a biaryl moiety. Three chiral centers are obtained from the starting material L-xylose, while the other two were established (or modified) via three highly stereoselective transformations: Luche reduction (dr: 97/3), dynamic kinetic resolution of anomeric hemiacetal (dr: 95/5), and Lewis acid-promoted thiolation (dr: 1000/ 1). Global deprotection of the resulting penultimate intermediate with catalytic sodium methoxide followed by recrystallization furnishes sotagliflozin. The longest linear sequence consists of 10 steps from L-xylose with an overall yield of 40%. This process has been performed on multi-hundred kilogram batches to satisfy the drug substance development demands.

Total Synthesis of 5-Hydroxygoniothalamin

Patpi, Santhosh Reddy,Jin, Guangyi,Kantevari, Srinivas

, p. 780 - 786 (2019/01/23)

The total synthesis of 5-hydroxygoniothalamin is achieved from commercially available l -xylose. The α,β-unsaturated-δ-lactone core is constructed in very good yield by utilizing one-carbon and two-carbon cis -Wittig olefinations and δ-lactonization using Yamaguchi conditions. Subsequent Grubbs cross-metathesis followed by desilylation results in 5-hydroxygoniothalamin.

COMPOSITIONS COMPRISING (2S,3R,4R,5S,6R)-2-(4- CHLORO-3-(4-ETHOXYBENZYL)PHENYL)-6-(METHYLTHIO)TETRAHYDRO-2H-PYRAN-3,4,5-TRIOL

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Paragraph 0089, (2018/11/27)

Pharmaceutical dosage forms useful for improving the cardiovascular and/or metabolic health of patients, particularly those suffering from type 2 diabetes, are disclosed, as well as methods of their manufacture.

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