Facile synthesis of unusual glycosyl carbamates and amino acid glycosides from propargyl 1,2-orthoesters as glycosyl donors

TY - JOUR

T1 - Facile synthesis of unusual glycosyl carbamates and amino acid glycosides from propargyl 1,2-orthoesters as glycosyl donors

AU - Shaikh, Ashif Y.

AU - Sureshkumar, Gopalsamy

AU - Pati, Debasish

AU - Gupta, Sayam Sen

AU - Hotha, Srinivas

PY - 2011/9/7

Y1 - 2011/9/7

N2 - Propargyl 1,2-O-orthoesters are exploited for the synthesis of 1,2-trans O-glycosides of protected amino acids. N-Fmoc- and N-Cbz protected serine/threonine - benzyl/methyl esters reacted well with glucosyl-, galactosyl-, mannosyl- and lactosyl- derived propargyl 1,2-orthoesters affording respective 1,2-trans glycosides in good yields under AuBr 3/4 Å MS Powder/CH 2Cl 2/rt. t-Boc serine derivative gave serine 1,2-orthoester and glycosyl carbamate. Optimized conditions enabled preparation of new glycosyl carbamates from N-Boc protected amines in a single step using gold catalysts and propargyl 1,2-orthoesters in excellent yields.

AB - Propargyl 1,2-O-orthoesters are exploited for the synthesis of 1,2-trans O-glycosides of protected amino acids. N-Fmoc- and N-Cbz protected serine/threonine - benzyl/methyl esters reacted well with glucosyl-, galactosyl-, mannosyl- and lactosyl- derived propargyl 1,2-orthoesters affording respective 1,2-trans glycosides in good yields under AuBr 3/4 Å MS Powder/CH 2Cl 2/rt. t-Boc serine derivative gave serine 1,2-orthoester and glycosyl carbamate. Optimized conditions enabled preparation of new glycosyl carbamates from N-Boc protected amines in a single step using gold catalysts and propargyl 1,2-orthoesters in excellent yields.

UR - http://www.scopus.com/inward/record.url?scp=80052041782&partnerID=8YFLogxK

U2 - 10.1039/c1ob05056g

DO - 10.1039/c1ob05056g

M3 - Journal article

C2 - 21483986

AN - SCOPUS:80052041782

SN - 1477-0520

VL - 9

SP - 5951

EP - 5959

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 17

ER -