Preparation of (S,S)-secoisolariciresinol diglucoside and (R,R)-secoisolariciresinol diglucoside
AssigneesThe Scripps Research Institute, The Trustees of the University of Pennsylvania
InventorsMelpo Christofidou-Solomidou, Kyriacos C. Nicolaou, Roman A. Valiulin, Nicholas Simmons, Philipp M. Heretsch
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Abstract
The invention relates to processes for preparing (S,S)-secoisolariciresinol diglucoside and (R,R)-secoisolariciresinol diglucoside and compositions comprising the same.
Claims103
A process for preparing a compound of formula ((S,S)-SDG-1) or a compound of formula ((R,R)-SDG-2)
- the process comprising:
- (a) reacting a compound of formula (6)
- with a compound of formula (7)
- to prepare a compound of formula ((S,S)-S3) or a compound of formula ((R,R)-S4), respectively
- (b) cleaving benzyl ethers of the compound of formula ((S,S)-S3) and benzyl ethers of the compound of formula ((R,R)-S4), followed by a separation procedure to prepare a compound of formula ((S,S)-8) or a compound of formula ((R,R)-9), respectively
- (c) deprotecting the compound of formula ((S,S)-8) or the compound of formula ((R,R)-9) to prepare the compound of formula ((S,S)-SDG-1) or the compound of formula ((R,R)-SDG-2), respectively.
A process for preparing a compound of formula ((S,S)-SDG-1) or a compound of formula ((R,R)-SDG-2)
- the process comprising:
- (a) reacting a compound of formula (S2)
- with a reducing agent to prepare a compound of formula (6)
- (b) reacting the compound of formula (6) with a compound of formula (7)
- to prepare a compound of formula ((S,S)-S3) or a compound of formula ((R,R)-S4), respectively
- (c) cleaving benzyl ethers of the compound of formula ((S,S)-S3) and benzyl ethers of the compound of formula ((R,R)-S4), followed by a separation procedure to prepare a compound of formula ((S,S)-8) or a compound of formula ((R,R)-9), respectively
- and
- (d) deprotecting the compound of formula ((S,S)-8) or the compound of formula ((R,R)-9) to prepare the compound of formula ((S,S)-SDG-1) or the compound of formula ((R,R)-SDG-2), respectively.
A process for preparing a compound of formula ((S,S)-SDG-1) or a compound of formula ((R,R)-SDG-2)
- the process comprising:
- (a) reacting a compound of formula (5)
- with a reducing agent to prepare a compound of formula (S1)
- (b) reacting the compound of formula (S1)
- with a benzylating agent to prepare a compound of formula (S2)
- (c) reacting the compound of formula (S2) with a reducing agent to prepare a compound of formula (6)
- (d) reacting the compound of formula (6) with a compound of formula (7)
- to prepare a compound of formula ((S,S)-S3)
- (e) cleaving benzyl ethers of the compound of formula ((S,S)-S3) and benzyl ethers of the compound of formula ((R,R)-S4), followed by a separation procedure to prepare a compound of formula ((S,S)-81 or a compound of formula ((R,R)-9), respectively
- and
- (f) deprotecting the compound of formula ((S,S)-8) or the compound of formula ((R,R)-9) to prepare the compound of formula ((S,S)-SDG-1) or the compound of formula ((R,R)-SDG-2), respectively.
A process for preparing a compound of formula ((S,S)-S3)
- the process comprising reacting a compound of formula (6)
- with a compound of formula (7)
- to prepare the compound of formula ((S,S)-S3).
A process for preparing a compound of formula ((S,S)-8)
- the process comprising:
- (a) reacting a compound of formula (6)
- with a compound of formula (7)
- to prepare a compound of formula ((S,S)-S3)
- and
- (b) cleaving benzyl ethers of the compound of formula ((S,S)-S3), followed by a separation procedure to prepare the compound of formula ((S,S)-8).
A process for preparing a compound of formula ((R,R)-S4)
- the process comprising:
- (a) reacting a compound of formula (6)
- with a compound of formula (7)
- to prepare a compound of formula ((R,R)-S4).
A process for preparing a compound of formula ((R,R)-9)
- the process comprising:
- (a) reacting a compound of formula (6)
- with a compound of formula (7)
- to prepare a compound of formula ((R,R)-S4)
- (b) cleaving benzyl ethers of the compound of formula ((R,R)-S4), followed by a separation procedure to prepare a compound of formula ((R,R)-9).
Dependencies are inferred from the claim text.