US 12,473,321 B2
Compositions and methods for phosphoramidite and oligonucleotide synthesis
David Charles Donnell Butler, Medford, MA (US); Pachamuthu Kandasamy, Lexington, MA (US); Subramanian Marappan, Acton, MA (US); Ik-Hyeon Paik, Needham, MA (US); Jayakanthan Kumarasamy, Arlington, MA (US); and Gopal Reddy Bommineni, Belmont, MA (US)
Assigned to WAVE LIFE SCIENCES LTD., Singapore (SG)
Filed by WAVE LIFE SCIENCES LTD., Singapore (SG)
Filed on Nov. 28, 2023, as Appl. No. 18/522,146.
Application 18/522,146 is a division of application No. 16/463,328, granted, now 11,873,316, previously published as PCT/US2017/062996, filed on Nov. 22, 2017.
Claims priority of provisional application 62/426,079, filed on Nov. 23, 2016.
Prior Publication US 2024/0368207 A1, Nov. 7, 2024
Int. Cl. C07H 1/06 (2006.01); C07H 19/10 (2006.01); C07H 19/207 (2006.01); C07H 21/00 (2006.01)
CPC C07H 1/06 (2013.01) [C07H 19/10 (2013.01); C07H 19/207 (2013.01); C07H 21/00 (2013.01)] 10 Claims
 
1. A composition comprising a compound having the structure of formula I:

OG Complex Work Unit Chemistry
or a salt thereof and a silylating reagent;
BA is

OG Complex Work Unit Chemistry
SU is

OG Complex Work Unit Chemistry
 wherein SU is connected to the phosphorus atom in formula I through the oxygen atom;
R5s is R′ or —OR′;
R2s is —H, —F, —CN, —N3, —NO, —NO2, —O—(C1-10 alkyl), or —O-(optionally substituted C1-6 alkylene)-OR′, or R2s is L connecting C2 with C1, C2, C3, C4 or C5, wherein L is —O—CH2— wherein the —CH2— is optionally substituted;

OG Complex Work Unit Chemistry
 each R′ is independently —R, —C(O)R, —CO2R, or —SO2R, or:
two or more R′ are taken together with their intervening atoms to form an optionally substituted monocyclic, bicyclic or polycyclic, saturated, partially unsaturated, or aryl 3-30 membered ring having, in addition to the intervening atoms, 0-10 heteroatoms independently selected from oxygen, nitrogen, sulfur, phosphorus and silicon; and
each R is independently hydrogen, or an optionally substituted group selected from C1-30 aliphatic, C1-30 heteroaliphatic having 1-10 heteroatoms independently selected from oxygen, nitrogen, sulfur, phosphorus and silicon, C6-30 aryl, a 5-30 membered heteroaryl ring having 1-10 heteroatoms independently selected from oxygen, nitrogen, sulfur, phosphorus and silicon, and a 3-30 membered heterocyclic ring having 1-10 heteroatoms independently selected from oxygen, nitrogen, sulfur, phosphorus and silicon.