23788-74-1
23788-74-1 結(jié)構(gòu)式
基本信息
1,3-DIOXOLANE-4-METHANOL, 2,2-DIMETHYL-, 4-METHYLBENZENESULFONATE, (4R)-
D-(-)-1,2-ISOPROPYLIDENEGLYCEROL 3-(P-TOLUENESULFONATE)
D-ALPHA,BETA-ISOPROPYLIDENEGLYCEROL-GAMMA-TOSYLATE
(R)-1,2-O-ISOPROPYLIDENEGLYCEROL-3-TOLUENESULFONATE
(R)-(-)-2,2-DIMETHYL-1,3-DIOXOLAN-4-YLMETHYL P-TOLUENESULFONATE
(R)-2,2-DIMETHYL-1,3-DIOXOLANE-4-METHANOL-4-METHYLBENZENESULFONATE
(R)-2,2-DIMETHYL-1,3-DIOXOLANE-4-METHANOL TOLUENE-4-SULFONATE
(R)-2,2-DIMETHYL-1,3-DIOXOLANE-4-METHANOL TOSYLATE
(R)-(-)-2,2-DIMETHYL-1,3-DIOXOLANE-4-YLMETHYL P-TOLUENESULFATE
(R)-(-)-2,2-DIMETHYL-1,3-DIOXOLANE-4-YLMETHYL P-TOLUENESULFONATE
(R)-(-)-2,2-DIMETHYL-4-(HYDROXYMETHYL)-1,3-DIOXOLANE-P-TOLUENESULFONATE
(R)-2,2-DIMETHYL-4-(HYDROXYMETHYL)-1,3-DIOXOLANE-P-TOLUENESULFONATE
(R)-(-)-2,2-DIMETHYL-4-(HYDROXYMETHYL)-1,3-DIOXOLANE-P-TOLUENSULFONATE
(R)-3-TOSYLOXY-1,2-PROPANEDIOL ACETONIDE
RARECHEM AK HZ 0035
(R)-O-ISOPROPYLIDENE GLYCEROL TOSYLATE
(R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-ylmethyl p-toluenosulfate
(R)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonate
(R)-(-)-2,2-Dimethyl-1,3-dioxolane-4-methanol-4-toluenesulfonate
物理化學(xué)性質(zhì)
安全數(shù)據(jù)
制備方法
22323-82-6
98-59-9
23788-74-1
在冰浴條件下，于10分鐘內(nèi)分批向(S)-(+)-2,2-二甲基-4-(羥甲基)-1,3-二氧戊環(huán)(19a)(4.0g, 30.2mmol)的無水吡啶(50mL)溶液中加入對(duì)甲苯磺酰氯(6.18g, 31.7mmol)。將反應(yīng)混合物緩慢升至室溫并攪拌過夜，期間觀察到白色沉淀形成。反應(yīng)完成后，減壓除去吡啶，殘余物用乙酸乙酯(50mL)稀釋，依次用冷的1M HCl水溶液(2×150mL)、飽和NaHCO3溶液(100mL)和鹽水(200mL)洗滌。有機(jī)層經(jīng)無水Na2SO4干燥，過濾并濃縮，得到淺黃色油狀物。粗產(chǎn)物通過硅膠柱色譜法純化，采用10-30%乙酸乙酯/己烷梯度洗脫，得到(R)-(-)-3-甲苯磺酰氧基-1,2-丙二醇丙酮化合物(20a)(8.54g, 99%收率, 99.9% ee)為無色粘性油狀物。Rf = 0.37(20%乙酸乙酯/己烷)。[α]D20 -4.8(c 1.0, EtOH)(文獻(xiàn)值[α]D24 -4.6(c 13.0, EtOH))。FTIR(薄膜)νmax 3073, 2987, 2937, 2891, 1598, 1495, 1455, 1368, 1257, 1213, 1190, 1177, 1096, 1055, 979, 829, 788, 665, 555 cm-1。1H NMR(600MHz, CDCl3)δ1.31(s, 3H, CH3-2), 1.34(s, 3H, CH3-2), 2.45(s, 3H, ArCH3), 3.76(dd, J=5.1和8.8Hz, 1H, CH2-5), 3.98(dd, J=6.0和10.2Hz, 1H, CH2-1'), 3.99-4.05(m, 2H, CH2-1'和CH2-5), 4.28(m, 1H, CH-4), 7.35(m, 2H, 芳香H-3和H-5), 7.79(m, 2H, 芳香H-2和H-6) ppm。13C NMR(150MHz, CDCl3)δ21.5(Ar-CH3), 25.1(CH3-2), 26.5(CH3-2), 66.1(C-5), 69.4(C-1'), 72.8(C-4), 109.9(C-2), 127.9(2C, 芳香C-2和C-6), 129.8(2C, 芳香C-3和C-5), 132.6(芳香C-1), 145.0(芳香C-4) ppm。HRMS(ESI): C13H18NaO5S [M+Na]+計(jì)算值309.07672; 實(shí)測(cè)值309.0762。手性HPLC分析: Chiralpak IA柱(5μm, 250×4.6mm), 流動(dòng)相為己烷/2-丙醇/甲醇(97:2:1, v/v/v), 流速1.0mL/min, tR=21.71min(0.06% 20b), tR=24.20min(99.94% 20a), 99.88% ee。所有物理和光譜數(shù)據(jù)與文獻(xiàn)報(bào)道一致。
參考文獻(xiàn)：
[1] Tetrahedron, 2013, vol. 69, # 5, p. 1634 - 1648
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 8, p. 3198 - 3213
[3] Patent: WO2013/133730, 2013, A1. Location in patent: Page/Page column 33; 34
[4] Patent: US2015/31898, 2015, A1. Location in patent: Paragraph 0221; 0222
[5] Pharmazie, 1998, vol. 53, # 6, p. 377 - 380
| 報(bào)價(jià)日期 | 產(chǎn)品編號(hào) | 產(chǎn)品名稱 | CAS號(hào) | 包裝 | 價(jià)格 |
| 2025/05/22 | XW022378874102 | (R)-2,2-二甲基-1,3-二氧戊環(huán)基-4-甲基苯磺酸甲酯 | 23788-74-1 | 1G | 46元 |
| 2025/05/22 | XW022378874101 | (R)-2,2-二甲基-1,3-二氧戊環(huán)基-4-甲基苯磺酸甲酯 | 23788-74-1 | 250MG | 31元 |
| 2025/05/22 | D2549 | (R)-(-)-2,2-二甲基-1,3-二氧戊環(huán)基-4-基甲基對(duì)甲苯磺酸酯 (R)-(-)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-Toluenesulfonate | 23788-74-1 | 1G | 470元 |