23735-43-5
中文名称
(S)-(+)-2,2-二甲基-1,3-二氧环戊基-4-甲醇对甲基苯磺酸酯
英文名称
(S)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonate
CAS
23735-43-5
分子式
C13H18O5S
MDL 编号
MFCD00063234
分子量
286.34
MOL 文件
23735-43-5.mol
更新日期
2025/06/24 17:40:55
23735-43-5 结构式
基本信息
中文别名
2,2-二甲基-1,3-二丙烯甲酸酯(S)对甲基苯磺酸-2,2-二甲基-1,3-二氧戊环基-4-甲酯
(S)-(+)-2,2-二甲基-1,3-二氧环戊基-4-甲醇对甲基苯磺酸酯
英文别名
1,3-DIOXOLANE-4-METHANOL, 2,2-DIMETHYL-, 4-METHYLBENZENESULFONATE, (4S)-2,2-DIMETHYL-4(S)-4-(P-TOLYLSULFONYL)METHYL-1,3-DIOXALANE
2,3-ISOPROPYLIDENE-SN-GLYCEROL 1-TOSYLATE
L-(+)-1,2-ISOPROPYLIDENEGLYCEROL 3-(P-TOLUENESULFONATE)
L-ALPHA,BETA-ISOPROPYLIDENEGLYCEROL-GAMMA-TOSYLATE
(S)-1,2-O-ISOPROPYLIDENEGLYCEROL-3-TOLUENESULFONATE
(S)-(+)-2,2-DIMETHYL-1,3-DIOXOLAN-4-YLMETHYL P-TOLUENESULFONATE
(S)-2,2-DIMETHYL-1,3-DIOXOLANE-4-METHANOL-4-METHYLBENZENESULFONATE
(S)-2,2-DIMETHYL-1,3-DIOXOLANE-4-METHANOL TOLUENE-4-SULFONATE
(S)-2,2-DIMETHYL-1,3-DIOXOLANE-4-METHANOL TOSYLATE
(S)-(+)-2,2-DIMETHYL-1,3-DIOXOLANE-4-YLMETHYL P-TOLUENESULFONATE
(S)-(+)-2,2-DIMETHYL-4-(HYDROXYMETHYL)-1,3-DIOXOLANE-P-TOLUENESULFONATE
(S)-2,2-DIMETHYL-4-(HYDROXYMETHYL)-1,3-DIOXOLANE-P-TOLUENESULFONATE
(S)-(+)-2,2-DIMETHYL-4-(HYDROXYMETHYL)-1,3-DIOXOLANE-P-TOLUENSULFONATE
(S)-3-TOSYLOXY-1,2-PROPANEDIOL ACETONIDE
(S)-O-ISOPROPYLIDENE GLYCEROL TOSYLATE
(S)-2,2-Dimethyl-1,3-dioxolane-4-methanol p-toluenesulfonate
(S)-3-Toxyloxy-1,2-propanediol acetonide
(s)-2,2-dimethyl-1,3-dioxolane-4-methyl p-toluenesulfonate
(S)-(+)-2,2-Dimethyl-1,3-dioxolane-4-methanol 4-toluenesulfo
所属类别
化学试剂：有机试剂物理化学性质
熔点29-31 °C
比旋光度4.2 º (c=10, abs.alcohol)
沸点398.71°C (rough estimate)
密度1.208 g/mL at 25 °C(lit.)
折射率n20/D 1.506(lit.)
闪点>230 °F
储存条件2-8°C
形态powder to lump to clear liquid
颜色White or Colorless to Light yellow
旋光度 (Optical Rotation)[α]26/D +7.5°, c = 2% in DMF
BRN89799
InChIInChI=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
InChIKeySRKDUHUULIWXFT-LBPXTSNRNA-N
SMILESC1(C=CC(C)=CC=1)S(=O)(=O)OC[C@@H]1COC(C)(C)O1 |&1:12,r|
制备方法
方法1
98-59-9
14347-78-5
23735-43-5
以对甲苯磺酰氯和(R)-(-)-甘油醇缩丙酮为原料，合成(S)-(2,2-二甲基-1,3-二氧戊环-4-基)甲基4-甲基苯磺酸酯的一般步骤如下：按照制备(R)-(-)-20a的方法，将(R)-(-)-2,2-二甲基-4-(羟甲基)-1,3-二氧戊环(19b)(2.50g)转化为(S)-(+)-3-甲苯磺酰氧基-1,2-丙二醇丙酮化合物20b(5.23g，收率98%，ee值99.2%)。[α]D20 +4.5(c 1.0, EtOH)(文献值[α]D25 +4.7(c 1.0, EtOH))。IR、NMR和HRMS光谱数据与(R)-(-)-20a对映体完全一致。
参考文献：
[1] Chemical and Pharmaceutical Bulletin, 1995, vol. 43, # 10, p. 1719 - 1723
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 8, p. 3198 - 3213
[3] Tetrahedron, 2013, vol. 69, # 5, p. 1634 - 1648
[4] Journal of the American Chemical Society, 1980, vol. 102, # 20, p. 6304 - 6311
[5] Journal of the Chemical Society, Chemical Communications, 1984, # 6, p. 349 - 350
知名试剂公司产品信息
Acros Organics
（S）对甲基苯磺酸-2，2-二甲基-1，3-二氧戊环基-4-甲酯(S)-(+)-2,2-Dimethyl-4-(hydroxymethyl)-1,3-dioxolane-p-toluenesulfonate, 97%(23735-43-5)
Sigma Aldrich
23735-43-5(sigmaaldrich)