1、H3COHHHHOCH3HHH3COHHCH2CH3HOCH3HCH2CH3SOPH3CH2CH2CCH3PhH2CNCH2CHPhCH3CH2+HOH2CCHOHO HHOH2CCHOH OHCCHOCH2OHHOHCHOOHHCH2OHCCHOCH2OHHOHCHOHHOCH2OHDD-(+)-甘油醛L-(-)-甘油醛LCO2HHH2NCH2SHCCHOCH2OHHOHCHOOHHCH2OHDR-甘油醛L-半光氨酸R-半光氨酸CCCHHO2CHCO2HR-(-)- 戊二烯二酸S-（+）-螺環(huán)3，3-庚-1，5-二烯H3CH3CHHH3CHH3CHHH3CHH3CHOOHHHHOH2CCHO

2、HOHHOHHOH2CCHOHOHHHOHOH2CCHOHHHOHOHOH2CCHO2R,3R2S,3S2S,3R2R,3S非對映異構(gòu)體非對映異構(gòu)體非對映異構(gòu)體對映異構(gòu)體非對映異構(gòu)體2,3,4-三羥基丁醛中的立體異構(gòu)關(guān)系(H3C)2HCCO2HHPh(H3C)2HCCO2HPhHHNH2CH3Ph(H3C)2HCCO2HPhHR-(-)S-(+)外消旋混合物R-(+)非對映異構(gòu)的羧酸銨鹽（R-酸，R-胺和S-酸，R-胺）的混合物，從乙醇-水中重結(jié)晶重結(jié)晶后的產(chǎn)物：R，R鹽從濾液中回收的鹽富集了的S，R鹽酸化酸化R-(-)-酸部分拆分的S-（+）-酸OPhOOPhOPhCat*O*+CH2CHO

3、HTi(OR)4,t-BuOOHCH2CHOH(+)diisopropyl tartrate37% yield recovered, 95%e.e.OHOCH3NH2CO2HH+CO2OCH3H2N+racemicL-valine27% yield,96% d.e.CHCH3O2CCH3CHCH3OHRhizopus nigricansR-enantiomer,98%e.e.at 28% conversionOCO2C2H5PhCH2OCO2C2H5PhCH2OOHBakers yeast38% yield, 82% d.e., 84% e.e.(CH2)8OHHH3C(H2C)7H(CH2)

4、8OHHHH3C(H2C)7CH3CO3HCH3CO3HOHHH3C(H2C)7HO(H2C)8OHH3C(H2C)7HHO(H2C)8OSO2C6H4pCH3H3CH3C(H2C)5HOSO2C6H4pCH3H3CH3C(H2C)5HCH3CO2-CH3CO2-H3CO2CCH3H(CH2)5CH3H3CO2CHH3C(CH2)5CH3BrHPhH3CPhHKOCH2CH3PhHH3CPhBrHPhH3CHPhKOCH2CH3HPhH3CPh蘇型赤型；HN(CH3)2PhHH3CCH3-OCH3H3CPhHHN(CH3)2PhCH3H3CH-OHH3CPhCH3+115+蘇型赤型125;Ph

5、OCH2ClHHHOPhHHOPhHn-BuLi /乙醚+(26%)(14%)PhCH3CHOHCH3MgIPhCH3HOHCH3HPhCH3HOHHCH3+赤型（67%）蘇型（33%）O(H3C)3CLiAlH4(H3C)3CHOH(H3C)3COHH+(90%)(10%)PhCH3ClHOH-HOCH3HPhPhCH3OHH+C XR1R2R3C+R1R2R3-X-Nu-C NuR1R2R3+CR1R2R3NuPure enantiomerachiral intermediateracemic productHOOHH HHOOHD HHOOHH DHOOHHHHOOHHDHOOHDHR-1-氘-1,3-丙二醇S-1-氘-1,3-丙二醇HOOHHHHOOHHDHOOHDHR-1-氘-1