23788-74-1
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
物理化学性质
| 熔点 | 41-43 °C(lit.) |
| 沸点 | 398.71°C (rough estimate) |
| 密度 | 1.208 g/mL at 25 °C(lit.) |
| 折射率 | n |
| 闪点 | >230 °F |
| 储存条件 | −20°C |
| 溶解度 | 可溶于二氯甲烷；氯仿；乙酸乙酯;甲醇；DMF； |
| 形态 | Oil |
| 颜色 | 浅棕色 |
| 旋光度 (Optical Rotation) | [α]/D 7.0±0.5°, neat |
| BRN | 89800 |
| InChI | InChI=1/C13H18O5S/c1-10-4-6-12(7-5-10)19(14,15)17-9-11-8-16-13(2,3)18-11/h4-7,11H,8-9H2,1-3H3/t11-/s3 |
| InChIKey | SRKDUHUULIWXFT-LLVKDONJSA-N |
| SMILES | C1(C=CC(C)=CC=1)S(=O)(=O)OC[C@H]1COC(C)(C)O1 |&1:12,r| |
| CAS 数据库 | 23788-74-1(CAS DataBase Reference) |
安全数据
| 危险性符号(GHS) |  GHS07 |
| 警示词 | 警告 |
| 危险性描述 | H315-H319 |
| 防范说明 | P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 |
| 危险品标志 | Xi,Xn |
| 危险类别码 | R36/37/38-R22 |
| 安全说明 | S26-S36-S37/39 |
| WGK Germany | 3 |
| F | 10-21 |
| 海关编码 | 29329900 |
| 存储类别 | 11 - Combustible Solids |
制备方法
22323-82-6
98-59-9
23788-74-1
在冰浴条件下，于10分钟内分批向(S)-(+)-2,2-二甲基-4-(羟甲基)-1,3-二氧戊环(19a)(4.0g, 30.2mmol)的无水吡啶(50mL)溶液中加入对甲苯磺酰氯(6.18g, 31.7mmol)。将反应混合物缓慢升至室温并搅拌过夜，期间观察到白色沉淀形成。反应完成后，减压除去吡啶，残余物用乙酸乙酯(50mL)稀释，依次用冷的1M HCl水溶液(2×150mL)、饱和NaHCO3溶液(100mL)和盐水(200mL)洗涤。有机层经无水Na2SO4干燥，过滤并浓缩，得到浅黄色油状物。粗产物通过硅胶柱色谱法纯化，采用10-30%乙酸乙酯/己烷梯度洗脱，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)为无色粘性油状物。Rf = 0.37(20%乙酸乙酯/己烷)。[α]D20 -4.8(c 1.0, EtOH)(文献值[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]+计算值309.07672; 实测值309.0762。手性HPLC分析: Chiralpak IA柱(5μm, 250×4.6mm), 流动相为己烷/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。所有物理和光谱数据与文献报道一致。
参考文献：
[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
知名试剂公司产品信息
(R)-(-)-2,2-Dimethyl-4-(hydroxymethyl)-1,3-dioxolane-p-toluenesulfonate, 97%(23788-74-1) Acros Organics
(R)对甲基苯磺酸-2,2-二甲基-1,3-二氧戊环基-4-甲酯价格(试剂级)
| 报价日期 | 产品编号 | 产品名称 | CAS号 | 包装 | 价格 |
| 2026/09/15 | XW022378874102 | (R)-2,2-二甲基-1,3-二氧戊环基-4-甲基苯磺酸甲酯 | 23788-74-1 | 1G | 46元 |
| 2026/09/15 | XW022378874101 | (R)-2,2-二甲基-1,3-二氧戊环基-4-甲基苯磺酸甲酯 | 23788-74-1 | 250MG | 31元 |
| 2026/09/15 | D2549 | (R)-(-)-2,2-二甲基-1,3-二氧戊环基-4-基甲基对甲苯磺酸酯 (R)-(-)-2,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-Toluenesulfonate | 23788-74-1 | 1G | 310元 |