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US 11,008,358 B2Granted
Synthesis of desosamines
AssigneePresident and Fellows of Harvard College
InventorsAndrew G. Myers, Ziyang Zhang
Life of this patent
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Abstract
The present invention provides desosamine and mycaminose analogs and nitro sugars and methods for their preparation. The invention also provides methods of cyclizing a compound of Formula (A′) with glyoxal to give a nitro sugar of Formula (B). Methods for the preparation of compound of Formula (D′) are provided comprising cyclization of a nitro alcohol to give a nitro sugar and reduction and alkylation of the nitro sugar to give a desosamine, mycaminose, or an analog thereof.
Claims20
A compound of Formula (J):
- or salt thereof, wherein:
- R1a is —N(RS)2, —NRS(ORS), or of formula:
- each of R2a and R3a is independently hydrogen, halogen, optionally substituted C1-C6 alkyl, or —ORSO;
- XS is a bond, —C(═O)—, —C(═NRSN)—, —S(═O)—, or —S(═O)2—;
- LS2 is a bond, —NRS—, —O—, or —S—, or a linking group selected from the group consisting of optionally substituted alkylene, optionally substituted alkenylene, optionally substituted alkynylene, optionally substituted heteroalkylene, optionally substituted heteroalkenylene, and optionally substituted heteroalkynylene, and combinations thereof;
- each RS is independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted carbocyclyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl, an oxygen protecting group when attached to an oxygen atom, a nitrogen protecting group when attached to a nitrogen atom, or a sulfur protecting group when attached to a sulfur atom, or two RS attached to the same nitrogen atom are taken together to form ═N2 or an optionally substituted heterocyclyl or heteroaryl ring;
- each of R7a and R8a is independently optionally substituted C1-C6 alkyl, optionally substituted carbocyclyl, optionally substituted aryl, optionally substituted heterocyclyl, optionally substituted heteroaryl, optionally substituted acyl, or a nitrogen protecting group, or R7a and R8a are joined to form an optionally substituted heterocyclyl or heteroaryl ring;
- each RSN is independently hydrogen, optionally substituted C1-C6 alkyl, or a nitrogen protecting group, or two RSN attached to the same nitrogen atom are joined to form an optionally substituted heterocyclyl or heteroaryl ring;
- each of R4a and R4b is independently hydrogen, halogen, optionally substituted C1-C6 alkyl, or —ORSO;
- and
- each of R5, R6 and RSO is independently hydrogen, optionally substituted C1-C6 alkyl, a carbohydrate, or an oxygen protecting group;
- provided R1a is not:
9 more elements
A compound of Formula (K):
- or salt thereof, wherein:
- R1b is —N(RS)2, —NRS(ORS), or of formula:
- each of R2b and R3b is independently hydrogen, halogen, optionally substituted C1-C6 alkyl, or —ORSO;
- XS is a bond, —C(═O)—, —C(═NRSN)—, —S(═O)—, or —S(═O)2—;
- LS2 is a bond, —NRS—, —O—, or —S—, or a linking group selected from the group consisting of optionally substituted alkylene, optionally substituted alkenylene, optionally substituted alkynylene, optionally substituted heteroalkylene, optionally substituted heteroalkenylene, and optionally substituted heteroalkynylene, and combinations thereof;
- each RS is independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted carbocyclyl, optionally substituted heterocyclyl, optionally substituted aryl, optionally substituted heteroaryl, an oxygen protecting group when attached to an oxygen atom, a nitrogen protecting group when attached to a nitrogen atom, or a sulfur protecting group when attached to a sulfur atom, or two RS attached to the same nitrogen atom are taken together to form ═N2 or an optionally substituted heterocyclyl or heteroaryl ring;
- RSN is hydrogen, optionally substituted alkyl, or a nitrogen protecting group;
- each of R4a and R4b is independently hydrogen, optionally substituted C1-C6 alkyl, or —ORSO;
- and
- each of R5, R6 and RSO is independently hydrogen, halogen, optionally substituted C1-C6 alkyl, a carbohydrate, or an oxygen protecting group;
- provided R1b is not:
8 more elements
Dependencies are inferred from the claim text.