# US 2021/0277032 A1 · Scalable polypropionate lactone stereotetrads

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- Number: US 2021/0277032 A1
- Document ID: US20210277032A1
- Status: Published application
- Kind: A1
- Application number: 17/070,115
- Filed: 2020-10-14
- Published: 2021-09-09
- Earliest claimed: 2016-12-09
- Assignees: Akanocure Pharmaceuticals, Inc.
- Applicants: Akanocure Pharmaceuticals, Inc.
- Inventors: Mohammad N. NOSHI; Philip L. FUCHS
- Web page: https://patentgrep.com/patent/US20210277032A1

## CPC

- C07D 309/30: Oxygen atoms, e.g. delta-lactones
- C07F 7/1804: {Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896)}
- C07F 7/04: Esters of silicic acids
- C07B 2200/13: Crystalline forms, e.g. polymorphs
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

The present technology is directed to polypropionate lactone stereotetrads of Formula (I) (or a pharmaceutically acceptable salt and/or solvate thereof) which are significant intermediates for multiple synthetic applications.

## Claims

### Claim 1

A compound of any one of Formulas I2, I4, I6, I7, and I9-I11:
or a pharmaceutically acceptable salt and/or solvate thereof, wherein
R1 is independently at each occurrence H, trimethylsilyl (TMS), triethylsilyl (TES), tert-butyl-dimethylsilyl (TBS), triisopropylsilyl (TIPS), tert-butyl-diphenylsilyl (TBDPS), triphenylsilyl, dimethylphenylsilyl, methyldiphenylsilyl, acetyl (Ac), pivaloyl (Piv), trichloroacetyl, 2,2,2-trichloroethoxycarbonyl (Troc), benzyl, p-methoxybenzyl (PMB), 3-(phenylsulfonyl)propionyl, tosyl (Ts), or mesyl (Ms);
R2 is independently at each occurrence H, TMS, TES, TBS, TIPS, TBDPS, triphenylsilyl, dimethylphenylsilyl, methyldiphenylsilyl, Ac, Piv, trichloroacetyl, Troc, benzyl, PMB, 3-(phenylsulfonyl)propionyl, Ts, or Ms; and
n is independently at each occurrence 1 or 2.

### Claim 2

(canceled)

### Claim 3 (depends on 1)

The compound of claim 1, wherein R1 is TBS or acetyl; and/or R2 is triphenylsilyl.

### Claim 4 (depends on 3)

The compound of claim 3, wherein the compound of Formula I is a crystalline solid.

### Claim at position 5

-7. (canceled)

### Claim 8 (depends on 1)

The compound of claim 1, wherein the compound is of Formula I2:
or a pharmaceutically acceptable salt and/or solvate thereof.

### Claim 9

(canceled)

### Claim 10 (depends on 1)

The compound of claim 1, wherein the compound is of Formula I4:
or a pharmaceutically acceptable salt and/or solvate thereof.

### Claim 11

(canceled)

### Claim 12 (depends on 1)

The compound of claim 1, wherein the compound is of Formula I6:
or a pharmaceutically acceptable salt and/or solvate thereof.

### Claim 13 (depends on 1)

The compound of claim 1, wherein the compound is of Formula I7:
or a pharmaceutically acceptable salt and/or solvate thereof.

### Claim 14

(canceled)

### Claim 15 (depends on 1)

The compound of claim 1, wherein the compound is of Formula I9:
or a pharmaceutically acceptable salt and/or solvate thereof.

### Claim 16 (depends on 1)

The compound of claim 1, wherein the compound is of Formula I10:
or a pharmaceutically acceptable salt and/or solvate thereof.

### Claim 17 (depends on 1)

The compound of claim 1, wherein the compound is of Formula I11:
or a pharmaceutically acceptable salt and/or solvate thereof.

### Claim at position 16

-23. (canceled)

### Claim 24

A compound of Formula I5 or Formula I8:
or a pharmaceutically acceptable salt and/or solvate thereof, wherein
R1 is independently at each occurrence H, trimethylsilyl (TMS), triethylsilyl (TES), tert-butyl-dimethylsilyl (TBS), triisopropylsilyl (TIPS), tert-butyl-diphenylsilyl (TBDPS), triphenylsilyl, dimethylphenylsilyl, methyldiphenylsilyl, acetyl (Ac), pivaloyl (Piv), trichloroacetyl, 2,2,2-trichloroethoxycarbonyl (Troc), benzyl, p-methoxybenzyl (PMB), 3-(phenylsulfonyl)propionyl, tosyl (Ts), or mesyl (Ms);
R2 is independently at each occurrence TMS, TES, TBS, TIPS, TBDPS, triphenylsilyl, dimethylphenylsilyl, methyldiphenylsilyl, Ac, Piv, trichloroacetyl, Troc, benzyl, PMB, 3-(phenylsulfonyl)propionyl, Ts, or Ms; and
n is 1 or 2.

### Claim 25 (depends on 24)

The compound of claim 24, wherein R1 is TBS or acetyl; and/or R2 is triphenylsilyl.

### Claim 26 (depends on 25)

The compound of claim 25, wherein the compound is a crystalline solid.