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By Seymour Bernstein, J.P. Dusza, J.P. Joseph

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13- D -G LUCOPYRANOSIDURONIC ACID Enzymatic, synthesis (57-10>. 51 17 jS-Hydroxyandrost-4-ene-3 ,ll-dione (11-Ketotestosterone) 17-jS-D-GLUCOPYRANOSIDURONIC ACID Enzymatic synthesis (57 -10). HO 3fl-Hydroxyandrost-5-ene-7 ,17 -dione (7 -Ketodehydroisoandrosterone, 7-Ketodehydroepiandrosterone) 3-SULFATE Sodium salt - ClgH25NaOsS·2H20 (anal. C, H), mp 162-165°, IR (61-1) (62-2) (65-11). Allied Characterization Data 3-SULFATE CC (62-1) • PC (62-1) (62-2) (66-32). 53 o 5 a-Androstane-3 ,17 -dione (Androstanedione) ,B-D-GLUCOPYRANOSIDURONIC ACID (Unspecified Location) PC, TLC (67-19).

17-I'l-D-GLUCOPYRANOSIDURONIC ACID Acid - C 24 H3Pg, mp 253-256° (64-4) (67 -10) • mp 262- 263° (65-7) • C24H3209·H20 (anal. 29) (67-22). m· Sodium salt - C24H31NaOg '3Hp (anal. C, H), mp (67-10) • PC, TLC (65-7). > 310° 39 2' ,3' ,4' -Tri- a-acetyl methyl ester - C31H40012 'H 20 (anal. ;;:~;ane 281 and 288 mfJ. 30) (67-22). '3-D-GLUCOPYRANOSIDURONIC ACID-3-BENZYL ETHER 2',3',4'-Tri-a-acetyl methyl ester - C3sH4S012 (anal. ~~~ane 279 and 287 mfJ. 26), TLC (67 -22). '3-D-GLUCOPYRANOSIDURONIC ACID-3-BENZYL ETHER16-ACETATE 2' ,3' ,4'-Tri-a-acetyl methyl ester - C4oH4S013 (anal.

30 3-SULFATE-17-ACETATE Sodium salt - C20H2SNa06S'H20 (anal. acetyl), [a]D + 14° (33% ethanol), A~f~ ethanol 269 and 275 mil (E 771 and 696) (68-4) . Triethylammonium salt - C26H41NOsS (anal. C, H, N, S), mp 142-145°, [a]~ + 31° (chloroform), A~i;ranoI269 and 275 mil, NMR (68-3). 17-SULFATE Sodium salt - CIBH23NaO~S'HfO (anal. \er 276278 mil (E 1770), [a]~ + 16° (water), [a]:g; + 42S (alcohol) (50-5) • CIBH23NaOsS'2H20 (anal. C, H, S, HP), [a]D + 35° (33% ethanol), A ~Of~ethanoI279 mil (E 1978) (68-4) • CIBH~fiNa05S'4HP (anal.

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