Takeda Chemical Industries, Inc.

Keiichi Sugimoto

Hiroshi Akimoto

Tadashi Hanaoka

Nobuharu Kakeya

Koji Nishijima

Yukio Mizuno

A method of producing (S)-glyceraldehyde acetonide, which comprises reacting 3,4-O-isopropylidene-L-threonic acid or a salt thereof with hypochlorite ion or hypochlorous acid under an acid condition. Also a method of producing (S)-glyceraldehyde acetonide, which comprises reacting 5,6-O-isopropylidene-L-ascorbic acid or a salt thereof with an oxidizing agent to produce 3,4-O-isopropylidene-L-threonic acid or a salt thereof and then reacting the 3,4-O-isopropylidene-L-threonic acid or a salt thereof with hypochlorite ion or hypochlorous acid under an acid condition. Also a method for producing (S)-glyceraldehyde acetonide, which comprises (1) reacting L-ascorbic acid or a salt thereof with acetone or a conventional equivalent thereof to produce 5,6-O-isopropylidene-L-ascorbic acid or a salt thereof; (2) reacting the 5,6-O-isopropylidene-L-ascorbic acid or a salt thereof with an oxidizing agent to produce 3,4-O-isopropylidene-L-threonic acid or a salt thereof; and (3) reacting the 3,4-O-isopropylidene-L-threonic acid or a salt thereof with hypochlorite ion or hypochlorous acid under an acid condition.

Method of producing (S)-glyceraldehyde acetonide

Novel penicillins of the formula ##STR1## wherein R is a branched chain alkyl group of from 3 to 14 carbon atoms, and their pharmaceutically acceptable salts, are easily absorbed in the blood and tissues through oral administration and show excellent antimicrobial activity against Gram-positive and Gram-negative bacteria, particularly against microorganisms of the genus Pseudomonas, such as Pseudomonas aeruginosa.

.alpha.-Alkylsulfobenzyl penicillins

Novel d-.alpha.-isobutylsulfobenzylpenicillin hemi-solvate crystals of the formula: ##STR1## (wherein A is a solvent selected from the class consisting of alcohols, ketones, ethers and esters) have excellent antibacterial activities and improved stability in terms of shelf-life.

d-.alpha.-Isobutylsulfobenzylpenicillin hemi-solvate crystals

.alpha.-Sulfophenylacetic acid derivatives of the general formula: ##STR1## (wherein R is a substituted or unsubstituted primary alcohol, cyclic alcohol or phenol compound residue), which are of value as intermediates of antibacterial agents, are selectively produced in a high yield by bringing a diester compound of the general formula: ##STR2## (wherein R has the same meaning as defined above) into contact with a strong acid.

Process for producing alpha-sulfophenylacetic acid derivatives

.alpha.-Sulfophenylacetic acid derivatives of the general formula: ##EQU1## (wherein R is a substituted or unsubsituted primary alcohol, cyclic alcohol or phenol compound residue), which are of value as intermediates of antibacterial agents, are selectively produced in a high yield by bringing a diester compound of the general formula: ##EQU2## (wherein R has the same meaning as defined above) into contact with a strong acid.

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Kawanishi, Japan

Keiichi Sugimoto