TY - CHAP
T1 - Simplifying Access to 3, 4-Di-O-acetyl-1, 5 anhydro-2, 6-dideoxy-D- lyxo-hex-1-enitol (3, 4-Di-O-acetyl-d-fucal)
AU - Gagarinov, Ivan A.
AU - Srivastava, Apoorva D.
AU - Boons, Geert Jan
AU - Visansirikul, Satsawat
N1 - Publisher Copyright:
© 2018 by Taylor and Francis Group, LLC.
PY - 2017/10/5
Y1 - 2017/10/5
N2 - 196 N-Acetyl-d-fucosamine (d-FucNAc) is a rare sugar found in a variety of bacterial glycoconjugates. 1 Chemical synthesis of their repeating units heavily relies on the use of orthogonally protected d-FucNAc-derived building blocks, which are available from diverse precursors. 2 Azidonitration of the title 3, 4-di-O-acetyl-D-fucal2b, 3 (3, 4-di-O-acetyl-1, 5-anhydro-2, 6-dideoxy-d-lyxo-hex-1-enitol) has been routinely used in this laboratory to produce large quantities (>20.0 g) of d-fucosamine and derivatives thereof. Accessing the title compound 3 on a large scale from commercially available d-fucose is prohibitively expensive. We have developed a convenient, six-step procedure to produce this valuable compound in 34%-40% overall yield, starting from commercially available 1, 2:3, 4-di-O-isopropylidene-d-galactose.
AB - 196 N-Acetyl-d-fucosamine (d-FucNAc) is a rare sugar found in a variety of bacterial glycoconjugates. 1 Chemical synthesis of their repeating units heavily relies on the use of orthogonally protected d-FucNAc-derived building blocks, which are available from diverse precursors. 2 Azidonitration of the title 3, 4-di-O-acetyl-D-fucal2b, 3 (3, 4-di-O-acetyl-1, 5-anhydro-2, 6-dideoxy-d-lyxo-hex-1-enitol) has been routinely used in this laboratory to produce large quantities (>20.0 g) of d-fucosamine and derivatives thereof. Accessing the title compound 3 on a large scale from commercially available d-fucose is prohibitively expensive. We have developed a convenient, six-step procedure to produce this valuable compound in 34%-40% overall yield, starting from commercially available 1, 2:3, 4-di-O-isopropylidene-d-galactose.
UR - http://www.scopus.com/inward/record.url?scp=85135969873&partnerID=8YFLogxK
U2 - 10.1201/9781315120300-24
DO - 10.1201/9781315120300-24
M3 - Chapter
AN - SCOPUS:85135969873
SN - 9781498726917
T3 - Proven Synthetic Methods
SP - 195
EP - 200
BT - Carbohydrate Chemistry
A2 - Vogel, Christian
A2 - Murphy, Paul
PB - CRC Press
CY - Boca Raton
ER -