# US 4,380,652 A · Enamines of 6'-methylspectinomycin and process for preparing the same

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- Number: US 4,380,652 A
- Document ID: US4380652A
- Status: Granted
- Kind: A
- Application number: 06/285,165
- Filed: 1981-07-20
- Granted: 1983-04-19
- Earliest claimed: 1981-07-20
- Assignees: The Upjohn Company
- Inventors: David R. White
- Web page: https://patentgrep.com/patent/US4380652A

## CPC

- C07H 15/224: with only one saccharide radical directly attached to the cyclohexyl radical, e.g. destomycin, fortimicin, neamine
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)

## Abstract

A method for the preparation of 6'-methylspectinomycin and analogs thereof. Additionally provides novel intermediates utilized in said method.

## Claims

### Claim 1

A compound having the formula
wherein R is hydrogen or alkyl and R.sub.1, R.sub.4, R.sub.5, R.sub.8, and R.sub.9 are selected from the group consisting of hydrogen, lower alkyl, lower alkenyl, and lower alkylyl; B and B.sub.1 are the same or different and are selected from the group consisting of hydrogen, hydroxy, alkoxy, o-lower alkenyl, thio, thio-lower alkyl and thio-lower alkenyl; A is selected from the group consisting of oxygen and sulfur; R'.sub.2, R'.sub.3, R'.sub.6 and R'.sub.7 are selected from the group consisting of lower alkyl, lower alkenyl, lower alkynyl, and a blocking group selected from the group consisting of aralkoxycarbonyl, halogenated-alkoxycarbonyl and alkoxycarbonyl; with the proviso that one of R'.sub.2 and R'.sub.3 is always a blocking group, and that one of R'.sub.6 and R'.sub.7 is always a blocking group; and R.sub.10 is acyl.

### Claim 2 (depends on 1)

A compound according to claim 1 having the formula ##STR162## wherein R'.sub.2, R'.sub.3, R'.sub.6, R'.sub.7, R.sub.10, B and B.sub.1 are the same as in claim 1.

### Claim 3 (depends on 2)

A compound according to claim 2, where R'.sub.2 and R'.sub.6 are hydrogen, R'.sub.3 and R'.sub.7 are carbobenzyloxy, R.sub.10 is acetyl, B and B.sub.1 are hydroxy, so that the specific embodiment is the enamine of N,N'-dicarbobenzyloxy-2'-O-acetyl-4',5'-didehydrospectinomycin.

### Claim 4

A process for preparing a compound having the formula ##STR163## which comprises reacting a compound having the formula ##STR164## with, in an excess of an acetal of dimethylformamide wherein R is hydrogen or alkyl and R.sub.1, R.sub.4, R.sub.5, R.sub.8, and R.sub.9 are selected from the group consisting of hydrogen, lower alkyl, lower alkenyl, and lower alkynyl; B and B.sub.1 are the same or different and are selected from the group consisting of hydrogen, hydroxy, alkoxy, o-lower alkenyl, thio, thio lower alkyl and thio-lower alkenyl; A is selected from the group consisting of oxygen and sulfur; R'.sub.2, R'.sub.3, R'.sub.6 and R'.sub.7 are selected from the group consisting of lower alkyl, lower alkenyl, lower alkynyl, and a blocking group selected from the group consisting of aralkoxycarbonyl, halogenated-alkoxycarbonyl and alkoxycarbonyl; with the proviso that one of R'.sub.2 and R'.sub.3 is always a blocking group, and that one of R'.sub.6 and R'.sub.7 is always a blocking group; and R.sub.10 is acyl.

### Claim 5 (depends on 4)

A process according to claim 4 wherein the compound prepared has the formula ##STR165## wherein R'.sub.2, R'.sub.3, R'.sub.6, and R'.sub.7 are selected from the group consisting of lower alkyl and a blocking group and B and B.sub.1 are selected from the group consisting of hydrogen or lower alkoxy; and R.sub.10 is acyl.

### Claim 6 (depends on 5)

A process according to claim 5 wherein the compound prepared is the enamine of N,N'-dicarbobenzyloxy-2'-O-acetyl-4',5'-didehydrospectinomycin.