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3, 6-O-bridged pyranose inversion compound and process for producing B-O-pyranoside

Foreign code F120006455
File No. KG0064-US01
Posted date Apr 27, 2012
Country United States of America
Application number 86758209
Gazette No. 20100324275
Gazette No. 8445652
Date of filing Feb 13, 2009
Gazette Date Dec 23, 2010
Gazette Date May 21, 2013
International application number JP2009052416
International publication number WO2009102022
Date of international filing Feb 13, 2009
Date of international publication Aug 20, 2009
Priority data
  • P2008-033960 (Feb 15, 2008) JP
  • 2009WO-JP52416 (Feb 13, 2009) WO
Title 3, 6-O-bridged pyranose inversion compound and process for producing B-O-pyranoside
Abstract (US8445652)
An object of the present invention is to provide a 3,6-O-bridged pyranose-inverted compound useful for being easy to produce beta-O-pyranosides selectively.
The 3,6-O-bridged pyranose-inverted compound according to the present invention is represented by General Formula (1): wherein RA and RB each represent hydrogen or are bonded to each other to form a benzene ring; one of RC and RD represents hydrogen and the other represents -OR2; R1 represents hydroxy or halogen; and R2 and R3 each represent a hydroxy-protecting group.
Scope of claims [claim1]
1. A 3,6-O-bridged pyranose-inverted compound, represented by the following formula:
wherein one of RC and RD represents hydrogen and the other represents -- OR2; R1 represents hydroxy or halogen; and R2 and R3 each represent a hydroxy-protecting group.
[claim2]
2. The 3,6-O-bridged pyranose-inverted compound according to claim 1, wherein RC represents hydrogen; and RD represents -- OR2.
[claim3]
3. The 3,6-O-bridged pyranose-inverted compound according to claim 1, wherein RC represents -- OR2; and RD represents hydrogen.
[claim4]
4. A 3,6-O-bridged pyranose-inverted compound, represented by the following formula:
wherein one of RC and RD represents hydrogen and the other represents -- OR2; R1 represents hydroxy or halogen; and R2 and R3 each represent a hydroxy-protecting group.
[claim5]
5. The 3,6-O-bridged pyranose-inverted compound according to claim 1, wherein the hydroxy-protecting group represented by R2 and R3 is benzyl, dimethyl benzyl, 4-methoxybenzyl, allyl or trialkyl silyl.
[claim6]
6. A process for producing beta -O-pyranoside represented by the following formula:
wherein one of RC and RD represents hydrogen and the other represents -- OR2; R2 and R3 each represent a hydroxy-protecting group; and R4 represents a residue of a primary, secondary or tertiary alcohol,
the process comprising reacting a 3,6-O-bridged pyranose-inverted compound represented by the following formula:
wherein X represents halogen; and RC, RD, R2 and R3 are the same as above,
with an alcohol represented by R4OH, wherein R4 is the same as above.
[claim7]
7. The 3,6-O-bridged pyranose-inverted compound according to claim 4, wherein RC represents hydrogen; and RD represents -- OR2.
[claim8]
8. The 3,6-O-bridged pyranose-inverted compound according to claim 4, wherein RC represents -- OR2; and RD represents hydrogen.
[claim9]
9. The 3,6-O-bridged pyranose-inverted compound according to claim 4, wherein the hydroxy-protecting group represented by R2 and R3 is benzyl, dimethyl benzyl, 4-methoxybenzyl, allyl or trialkyl silyl.
[claim10]
10. A process for producing beta -O-pyranoside represented by the following formula:
wherein one of RC and RD represents hydrogen and the other represents -- OR2; R2 and R3 each represent a hydroxy-protecting group; and R4 represents a residue of a primary, secondary or tertiary alcohol,
the process comprising reacting a 3,6-O-bridged pyranose-inverted compound represented by the following formula:
wherein X represents halogen; and RC, RD, R2 and R3 are the same as above,
with an alcohol represented R4OH, wherein R4 is the same as above.
  • Inventor, and Inventor/Applicant
  • YAMADA HIDETOSHI
  • ASAKURA NORIAKI
  • OKADA YASUNORI
  • KWANSEI GAKUIN
IPC(International Patent Classification)
U.S. Cl./(Sub)
  • C07H001/00
  • C07H009/02
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