TY - JOUR
AU - Ogawa, Seiichiro
AB - April, 1964] NOTES 587 Aminocyclitols. II. Stereochemical Studies of 2-Amino-1, 3-cyclohexanediol By Tetsuo SUAMI and Seiichiro OGAWA (Received November 1, 1963) In connection with the previous studies of III with acetic anhydride and pyridine.2) Since 2-amino-1, 3-cyclohexanediols,1) an inversion there is only one mesyloxy group in II, the reaction of trans-O-acetyl-O-mesyl-2-acetamido- product III should have suffered from Walden 1, 3-cyclohexanediol (II) has been studied. II inversion only at the place where the mesyloxy is prepared by the mesylation of trans-O-acetyl- group had been linked. Thus, the previously- 2-acetamido-1, 3-cyclohexanediol (I)1) with mes- reported DL-configuration of III1,2) is further confirmed by the present experiments. yl chloride and pyridine. The displacement of the mesyloxy group of II gives DL-O-acetyl- 2-acetamido-1, 3-cyclohexanediol (III) when the Experimental* reaction is carried out with sodium acetate in aqueous 2-methoxyethanol. III is identical trans -O-Acetyl -O- mesyl-2-acetamido-1, 3-cyclo- with an authentic sample2) which is prepared hexanediol (II).-To a stirred solution of 1.1g. of from trans-O-dimesyl-2-acetamido-1, 3-cyclohex- I in 15 ml. of pyridine, 0.8 ml. of methanesulfonyl anediol. The demesylation of II takes place chloride was added under ice cooling. After it had been stirred for 4 hr. at room temperature, the in boiling water without sodium 
TI - Aminocyclitols. II. Stereochemical Studies of 2-Amino-1,3-cyclohexanediol
JF - Bulletin of the Chemical Society of Japan
DO - 10.1246/bcsj.37.587
DA - 2006-03-27
UR - https://www.deepdyve.com/lp/oxford-university-press/aminocyclitols-ii-stereochemical-studies-of-2-amino-1-3-NKNTRSk2hh
SP - 587
EP - 588
VL - 37
IS - 4
DP - DeepDyve
ER -